In this assignment, I am asking you to reflect on the election of 2020. I have posted 5 interesting articles which I will briefly describe below. You must submit a thoughtful reflection (500 words)on the presidential election of 2020. You need to pick 1 article out of the 5 and use this article as the basis for your reflection. You don’t need to agree with the article you choose. None of the articles is about Joe Biden or Kamala Harris. Only 1 of the articles is written from an essentially pro-Trump perspective: “How Trump Lost,” by Peter Beinart. Two articles consider how Trump fits into the Republican Party: “How Greenwich Republicans Learned to Love Trump,” by Evan Osnos and “Why Trump Lost,” by Matt Maier. There will be legal challenges to the vote count in a number of states. Jane Mayer, in “Why Trump Can’t Afford to Lose,” spells out some of the personal stakes for Trump. Finally, even assuming the inauguration of Joe Biden in January, 2021, America still faces a challenge to its ability to continue as a democracy. We are becoming a nation whose government can’t agree on anything. Paul Krugman lays this out in, “Is America Becoming a Failed State?”You should include:A clear explanation of the major points that your chosen author makes.A clear explanation of how you respond to your author’s points.A Reporter at Large
November 9, 2020 Issue
Why Trump Can’t Afford to Lose

The President has survived one impeachment, twenty-six accusations of sexual misconduct, and
an estimated four thousand lawsuits. That run of good luck may well end, perhaps brutally, if Joe
Biden wins.
By Jane Mayer
November 1, 2020
Few people have evaded consequences more cunningly than Trump. His luck may run out if Joe
Biden defeats him.
The President was despondent. Sensing that time was running out, he had asked his aides
to draw up a list of his political options. He wasn’t especially religious, but, as daylight
faded outside the rapidly emptying White House, he fell to his knees and prayed out loud,
sobbing as he smashed his fist into the carpet. “What have I done?” he said. “What has
happened?” When the President noted that the military could make it easy for him by
leaving a pistol in a desk drawer, the chief of staff called the President’s doctors and
ordered that all sleeping pills and tranquillizers be taken away from him, to insure that he
wouldn’t have the means to kill himself.
The downfall of Richard Nixon, in the summer of 1974, was, as Bob Woodward and Carl
Bernstein relate in “The Final Days,” one of the most dramatic in American history. That
August, the Watergate scandal forced Nixon—who had been cornered by self-incriminating
White House tape recordings, and faced impeachment and removal from office—to resign.
Twenty-nine individuals closely tied to his Administration were subsequently indicted, and
several of his top aides and advisers, including his Attorney General, John Mitchell, went to
prison. Nixon himself, however, escaped prosecution because his successor, Gerald Ford,
granted him a pardon, in September, 1974.
No American President has ever been charged with a criminal offense. But, as Donald
Trump fights to hold on to the White House, he and those around him surely know that if he
loses—an outcome that nobody should count on—the presumption of immunity that attends the
Presidency will vanish. Given that more than a dozen investigations and civil suits involving
Trump are currently under way, he could be looking at an endgame even more perilous than the
one confronted by Nixon. The Presidential historian Michael Beschloss said of Trump, “If he
loses, you have a situation that’s not dissimilar to that of Nixon when he resigned. Nixon spoke
of the cell door clanging shut.” Trump has famously survived one impeachment, two divorces,
six bankruptcies, twenty-six accusations of sexual misconduct, and an estimated four thousand
lawsuits. Few people have evaded consequences more cunningly. That run of good luck may
well end, perhaps brutally, if he loses to Joe Biden. Even if Trump wins, grave legal and
financial threats will loom over his second term.
Two of the investigations into Trump are being led by powerful state and city law-enforcement
officials in New York. Cyrus Vance, Jr., the Manhattan District Attorney, and Letitia James,
New York’s attorney general, are independently pursuing potential criminal charges related to
Trump’s business practices before he became President. Because their jurisdictions lie outside
the federal realm, any indictments or convictions resulting from their actions would be beyond
the reach of a Presidential pardon. Trump’s legal expenses alone are likely to be daunting. (By
the time Bill Clinton left the White House, he’d racked up more than ten million dollars in legal
fees.) And Trump’s finances are already under growing strain. During the next four years,
according to a stunning recent Times report, Trump—whether reëlected or not—must meet
payment deadlines for more than three hundred million dollars in loans that he has personally
guaranteed; much of this debt is owed to such foreign creditors as Deutsche Bank. Unless he can
refinance with the lenders, he will be on the hook. The Financial Times,
meanwhile, estimates that, in all, about nine hundred million dollars’ worth of Trump’s realestate debt will come due within the next four years. At the same time, he is locked in a dispute
with the Internal Revenue Service over a deduction that he has claimed on his income-tax forms;
an adverse ruling could cost him an additional hundred million dollars. To pay off such debts, the
President, whose net worth is estimated by Forbes to be two and a half billion dollars, could sell
some of his most valuable real-estate assets—or, as he has in the past, find ways to stiff his
creditors. But, according to an analysis by the Washington Post, Trump’s properties—especially
his hotels and resorts—have been hit hard by the pandemic and the fallout from his divisive
political career. “It’s the office of the Presidency that’s keeping him from prison and the
poorhouse,” Timothy Snyder, a history professor at Yale who studies authoritarianism, told me.
The White House declined to answer questions for this article, and if Trump has made plans for a
post-Presidential life he hasn’t shared them openly. A business friend of his from New York
said, “You can’t broach it with him. He’d be furious at the suggestion that he could lose.” In
better times, Trump has revelled in being President. Last winter, a Cabinet secretary told me
Trump had confided that he couldn’t imagine returning to his former life as a real-estate
developer. As the Cabinet secretary recalled, the two men were gliding along in a motorcade,
surrounded by throngs of adoring supporters, when Trump remarked, “Isn’t this incredible? After
this, I could never return to ordering windows. It would be so boring.”
Throughout the 2020 campaign, Trump’s national poll numbers have lagged behind Biden’s, and
two sources who have spoken to the President in the past month described him as being in a foul
mood. He has testily insisted that he won both Presidential debates, contrary to even his own
family’s assessment of the first one. And he has raged not just at the polls and the media but also
at some people in charge of his reëlection campaign, blaming them for squandering money and
allowing Biden’s team to have a significant financial advantage. Trump’s bad temper was visible
on October 20th, when he cut short a “60 Minutes” interview with Lesley Stahl. A longtime
observer who spent time with him recently told me that he’d never seen Trump so angry.
The President’s niece Mary Trump—a psychologist and the author of the tell-all memoir “Too
Much and Never Enough”—told me that his fury “speaks to his desperation,” adding, “He knows
that if he doesn’t manage to stay in office he’s in serious trouble. I believe he’ll be prosecuted,
because it seems almost undeniable how extensive and long his criminality is. If it doesn’t
happen at the federal level, it has to happen at the state level.” She described the “narcissistic
injury” that Trump will suffer if he is rejected at the polls. Within the Trump family, she said,
“losing was a death sentence—literally and figuratively.” Her father, Fred Trump, Jr., the
President’s older brother, “was essentially destroyed” by her grandfather’s judgment that Fred
was not “a winner.” (Fred died in 1981, of complications from alcoholism.) As the President
ponders potential political defeat, she believes, he is “a terrified little boy.”
Barbara Res, whose new book, “Tower of Lies,” draws on the eighteen years that she spent, off
and on, developing and managing construction projects for Trump, also thinks that the President
is not just running for a second term—he is running from the law. “One of the reasons he’s so
crazily intent on winning is all the speculation that prosecutors will go after him,” she said. “It
would be a very scary spectre.” She calculated that, if Trump loses, “he’ll never, ever
acknowledge it—he’ll leave the country.” Res noted that, at a recent rally, Trump mused to the
crowd about fleeing, ad-libbing, “Could you imagine if I lose? I’m not going to feel so good.
Maybe I’ll have to leave the country—I don’t know.” It’s questionable how realistic such talk is,
but Res pointed out that Trump could go “live in one of his buildings in another country,”
adding, “He can do business from anywhere.”
It turns out that, in 2016, Trump in fact made plans to leave the United States right after the
vote. Anthony Scaramucci, the former Trump supporter who served briefly as the White House
communications director, was with him in the hours before the polls closed. Scaramucci told me
that Trump and virtually everyone in his circle had expected Hillary Clinton to win. According to
Scaramucci, as he and Trump milled around Trump Tower, Trump asked him, “What are you
doing tomorrow?” When Scaramucci said that he had no plans, Trump confided that he had
ordered his private plane to be readied for takeoff at John F. Kennedy International Airport, so
that the next morning he could fly to Scotland, to play golf at his Turnberry resort. Trump’s
posture, Scaramucci told me, was to shrug off the expected defeat. “It was, like, O.K., he did it
for the publicity. And it was over. He was fine. It was a waste of time and money, but move on.”
Scaramucci said that, if 2016 is any guide, Trump would treat a loss to Biden more matter-offactly than many people expect: “He’ll go down easier than most people think. Nothing crushes
this guy.”
Mary Trump, like Res, suspects that her uncle is considering leaving the U.S. if he loses the
election (a result that she regards as far from assured). If Biden wins, she suggested, Trump will
“describe himself as the best thing that ever happened to this country and say, ‘It doesn’t deserve
me—I’m going to do something really important, like build the Trump Tower in Moscow.’ ”
Biden Calls for Unity in His First Speech as President-Elect
The notion that a former American President would go into exile—like a disgraced king or a
deposed despot—sounds almost absurd, even in this heightened moment, and many close
observers of the President, including Tony Schwartz, the ghostwriter of Trump’s first best-seller,
“The Art of the Deal,” dismiss the idea. “I’m sure he’s terrified,” Schwartz told me. “But I don’t
think he’ll leave the country. Where the hell would he go?” However, Snyder, the Yale
professor, whose specialty is antidemocratic regimes in Eastern Europe, believes that Trump
might well abscond to a foreign country that has no extradition treaty with the U.S. “Unless
you’re an idiot, you have that flight plan ready,” Snyder said. “Everyone’s telling me he’ll have a
show on Fox News. I think he’ll have a show on RT”—the Russian state television network.
In Snyder’s view, such desperate maneuverings would not have been necessary had Trump been
a more adept autocrat. Although the President has recently made various authoritarian gestures—
in June, he threatened to deploy the military against protesters, and in July he talked about
delaying the election—Snyder contends that Trump’s predicament “is that he hasn’t ruined our
system enough.” Snyder explained, “Generally, autocrats will distort the system as far as
necessary to stay in power. Usually, it means warping democracy before they get to where
Trump is now.” For an entrenched autocrat, an election is mere theatre—but the conclusion of
the Trump-Biden race remains unpredictable, despite concerns about voter suppression, disputed
ballot counts, and civil unrest.
On Election Day, the margin of victory may be crucial in determining Trump’s future. If the
winner’s advantage in the Electoral College is decisive, neither side will be able to easily dispute
the result. But several of Trump’s former associates told me that if there is any doubt at all—no
matter how questionable—the President will insist that he has won. Michael Cohen, Trump’s
former attorney, told me, “He will not concede. Never, ever, ever.” He went on, “I believe he’s
going to challenge the validity of the vote in each and every state he loses—claiming ballot
fraud, seeking to undermine the process and invalidate it.” Cohen thinks that the recent rush to
confirm Amy Coney Barrett to the Supreme Court was motivated in part by Trump’s hope that a
majority of Justices would take his side in a disputed election.
Cohen, who pleaded guilty in 2018 to lying to Congress and to various financial crimes,
including making an illegal contribution to Trump’s Presidential campaign, has faced questions
about his credibility. But he affirmed, “I have heard that Trump people have been speaking to
lawyers all over the country, taking their temperatures on this topic.” One of Trump’s personal
attorneys, the Supreme Court litigator William Consovoy, has initiated legal actions across the
nation challenging mail-in voting, on behalf of the Republican Party, the Trump campaign, and a
dark-money group that calls itself the Honest Elections Project. And a former Trump White
House official, Mike Roman, who has made a career of whipping up fear about nonwhite voter
fraud, has assumed the role of field general of a volunteer fleet of poll watchers who refer to
themselves as the Army for Trump.
Cohen is so certain that Trump will lose that he recently placed a ten-thousand-dollar bet on it.
“He’ll blame everyone except for himself,” Cohen said. “Every day, he’ll rant and rave and yell
and scream about how they stole the Presidency from him. He’ll say he won by millions and
millions of ballots, and they cheated with votes from dead people and people who weren’t born
yet. He’ll tell all sorts of lies and activate his militias. It’s going to be a pathetic show. But, by
stacking the Supreme Court, he’ll think he can get an injunction. Trump repeats his lies over and
over with the belief that the more he tells them the more people will believe them. We all wish
he’d just shut up, but the problem is he won’t.”
Schwartz agreed that Trump “will do anything to make the case he didn’t lose,” and noted that
one of Trump’s strengths has been his refusal to admit failure, which means that “when he wins
he wins, and when he loses he also wins.” But if Trump loses by a landslide, Schwartz said,
“he’ll have many fewer cards to play. He won’t be able to play the election-was-stolen-from-me
card—and that’s a big one.”
It’s hard to imagine a former U.S. President behind bars or being forced to perform community
service, as the former Italian Prime Minister Silvio Berlusconi was, after being convicted of tax
fraud. Yet some of the legal threats aimed at Trump are serious. The case that Vance’s office, in
Manhattan, is pursuing appears to be particularly strong. According to court documents from the
prosecution of Cohen, he didn’t act alone. Cohen’s case centered on his payment of hush money
to the porn star Stormy Daniels, with whom the President allegedly had a sexual liaison. The
government claimed that Cohen’s scheme was assisted by an unindicted co-conspirator whom
federal prosecutors in the Southern District of New York referred to as “Individual-1,” and who
ran “an ultimately successful campaign for President of the United States.”
Clearly, this was a reference to Trump. But, because in recent decades the Justice Department
has held that a sitting President can’t be prosecuted, the U.S. Attorney’s office wrapped up its
case after Cohen’s conviction. Vance appears to have picked up where the U.S. Attorney left off.
The direction of Vance’s inquiry can be gleaned from Cohen’s sentencing memo: it disclosed
that, during the 2016 Presidential campaign, Cohen set up a shell company that paid a hundred
and thirty thousand dollars to Daniels. The Trump Organization disguised the hush-money
payment as “legal expenses.” But the government argued that the money, which bought her
silence, was an illegal campaign contribution: it helped Trump’s candidacy, by suppressing
damaging facts, and far exceeded the federal donation limit of twenty-seven hundred dollars.
Moreover, because the payment was falsely described as legal expenses, New York laws
prohibiting the falsification of business records may have been violated. Such crimes are usually
misdemeanors, but if they are committed in furtherance of other offenses, such as tax fraud, they
can become felonies. Court documents stated that Cohen “acted in coordination with and at the
direction of Individual-1”—an allegation that Trump has vehemently denied.
It has become clear that the Manhattan D.A.’s investigation involves more than the Stormy
Daniels case. Secrecy surrounds Vance’s grand-jury probe, but a well-informed source told me
that it now includes a hard-hitting exploration of potentially illegal self-dealing in Trump’s
financial practices. In an August court filing, the D.A.’s office argued that it should be allowed to
subpoena Trump’s personal and corporate tax records, explaining that it is now investigating
“possibly extensive and protracted criminal conduct at the Trump Organization.” The
prosecutors didn’t specify what the grand jury was looking into, but they cited news stories
detailing possible tax fraud, insurance fraud, and “schemes to defraud,” which is how New York
penal law addresses bank fraud. As the Times’ recent reports on Trump’s tax records show, he
has long made aggressive, and potentially fraudulent, use of accounting gimmicks to all but
eliminate his income-tax burden. One minor but revealing detail is that he deducted seventy
thousand dollars for hair styling, which ordinarily is a personal expense. At the same time,
according to congressional testimony that Cohen gave last year, Trump has provided insurance
companies with inflated income statements, in effect keeping two sets of books: one stating
losses, for the purpose of taxes, the other exaggerating profits, for business purposes. Trump’s
lawyers have consistently refused to disclose his tax records, fighting subpoenas in both the
circuit courts and the Supreme Court. Trump has denied any financial wrongdoing, and has
denounced efforts to scrutinize his tax returns as “a continuation of the worst witch hunt in
American history.” But his legal team has lost every round in the courts, and may be running out
of arguments. It’s possible that New York’s legal authorities will back off. Even a Trump critic
such as Scaramucci believes that “it’s too much of a strain on the system to put an American
President in jail.” But a former top official in New York suggested to me that Vance and James
are unlikely to abandon their investigations if Trump loses on November 3rd, if only because it
would send an unwanted message: “If you’re Tish James or Cy Vance and you drop the case the
moment he’s out of office, you’re admitting it was political.”
To get a conviction, the government would need to prove beyond a reasonable doubt that Trump
knowingly engaged in fraud. Prosecutors I spoke with said that this could be difficult. As Cohen
has noted, Trump writes little down, sends no e-mails or texts, and often makes his wishes
known through indirect means. There are also potential obstacles posed by statutes of limitation.
But prosecutors have clearly secured Cohen’s coöperation. Since Cohen began serving a threeyear prison sentence, at the federal correctional facility in Otisville, New York, he has been
interviewed by lawyers from Vance’s Major Economic Crimes Bureau no fewer than four times.
(Cohen was granted early release because of the pandemic.)
Norman Ornstein, a political scientist at the American Enterprise Institute, in Washington, D.C.,
and an outspoken Trump critic, said, “The odds are 99.9999 per cent that New York State
authorities have him on all kinds of tax fraud. We know these aren’t crimes that end up just with
fines.” Martin Flaherty, a founding director of the Leitner Center for International Law and
Justice, at Fordham University, and an expert in transitional justice, agreed: “I have to believe
Trump has committed enough ordinary crimes that you could get him.”
The question of what would constitute appropriate accountability for Trump—and serve to
discourage other politicians from engaging in similar, or worse, transgressions—has already
sparked debate. Flaherty, an authority on other countries’ struggles with state crimes, believes
that in America it would have “a salutary effect to have a completely corrupt guy getting thrown
in jail.” He acknowledged that Trump “might get pardoned,” but said, “A big problem since
Watergate is that élites don’t face accountability. It creates a culture of impunity that encourages
the shamelessness of someone like Trump.”
There are obvious political risks, though. Anne Milgram, a former attorney general of New
Jersey and a former Justice Department lawyer, suggested that Biden, should he win, is likely to
steer clear of any actions that would undermine trust in the impartiality of the justice system, or
re-galvanize Trump’s base. “The ideal thing,” she told me, would be for the Manhattan D.A.’s
office, not the Justice Department, to handle any criminal cases. Vance, she noted, is a
democratically elected local prosecutor in the city where the Trump Organization is based.
Unthinkable though it may be to imagine Trump doing time on Rikers Island, she said, “there’s
also a cost to a new Administration just turning the page and doing nothing.” Milgram continued,
“Trump will declare victory, and Trumpism won’t be over. It raises huge questions. It’s a fairly
impossible situation.”
Though Trump doesn’t have the power to pardon or commute a New York State court
conviction, he can pardon virtually anyone facing federal charges—including, arguably, himself.
When Nixon, a lawyer, was in the White House, he concluded that he had this power, though he
felt that he would disgrace himself if he attempted to use it. Nixon’s own Justice Department
disagreed with him when it was asked whether a President could, in fact, self-pardon. The acting
Assistant Attorney General, Mary C. Lawton, issued a memo proclaiming, in one sentence with
virtually no analysis, that, “under the fundamental rule that no one may be a judge in his own
case, it would seem that the question should be answered in the negative.” However, the memo
went on to suggest that, if the President were declared temporarily unable to perform the duties
of the office, the Vice-President would become the acting President, and in that capacity could
pardon the President, who could then either resign or resume the duties of the office.
To date, that is the only known government opinion on the issue, according to Jack Goldsmith,
who, under George W. Bush, headed the Justice Department’s Office of Legal Counsel and now
teaches at Harvard Law School. Recently, Goldsmith and Bob Bauer, a White House counsel
under Barack Obama, co-wrote “After Trump: Reconstructing the Presidency,” in which the
bipartisan pair offer a blueprint for remedying some of the structural weaknesses exposed by
Trump. Among their proposals is a rule explicitly prohibiting Presidents from pardoning
themselves. They also propose that bribery statutes be amended to prevent Presidents from using
pardons to bribe witnesses or obstruct justice.
Such reforms would likely come too late to stop Trump, Goldsmith noted: “If he loses—if—we
can expect that he’ll roll out pardons promiscuously, including to himself.” The President has
already issued forty-four pardons, some of them extraordinarily controversial: one went to his
political ally Joe Arpaio, the former Arizona sheriff who was convicted of criminal contempt in
his persistent violation of immigrants’ rights. Trump also commuted the sentence of his friend
Roger Stone, the political operative who was convicted of seven felonies, including witness
tampering, lying to federal investigators, and impeding a congressional inquiry. Other Presidents
have also granted questionable pardons. Bill Clinton’s decision to pardon the financier Marc
Rich, in 2001, not long after Rich’s former wife donated more than a million dollars to Clinton’s
Presidential library and to Democratic campaign war chests, was so redolent of bribery that it
provoked a federal investigation. (Clinton was cleared.) But, Goldsmith said, “no President has
abused the pardon power the same way that Trump has.” Given this pattern, he added, “I’d be
shocked if he didn’t pardon himself.” Jon Meacham, a Presidential historian, agreed. As he put it,
“A self-pardon would be the ultimate act of constitutional onanism for a narcissistic President.”
Whether a self-pardon would stand up to court review is another matter. “Its validity is
completely untested,” Goldsmith said. “It’s not clear if it would work. The pardon power is very,
very broad. But there’s no way to really know. Scholars are all over the map.”
Roberta Kaplan, a New York litigator, suggested the same scenario sketched out in Lawton’s
memo: Trump “could quit and be pardoned by Pence.” Kaplan represents E. Jean Carroll, who is
suing Trump for defamation because he denied her accusation that he raped her in a dressing
room at Bergdorf Goodman, in the nineteen-nineties. The suit, which a federal judge allowed to
move forward on October 27th, is one of many civil legal threats aimed at Trump. Although
Kaplan can imagine Trump trying to pardon himself, she believes that it would defy common
sense. She joked, “If that’s O.K., I might as well just pardon myself at Yom Kippur.”
Scholars today are far less united than they used to be about the wisdom of pardoning Presidents.
Ford’s pardon of Nixon is increasingly viewed with skepticism. Though Ford’s action generated
public outrage, a consensus eventually formed among Washington’s wise men that he had
demonstrated selfless statesmanship by ending what he called “our long national nightmare.”
Ford lost the 1976 election, partly because of the backlash, but he later won the John F. Kennedy
Profile in Courage Award for his decision, and he was lauded by everyone from Bob Woodward
to Senator Ted Kennedy. Beschloss, the historian, who interviewed Ford about the matter, told
me, “I believe he was right to offer the pardon but wrong not to ask for a signed confession that
Nixon was guilty as charged. As a result, Nixon spent the rest of his life arguing that he had done
nothing worse than any other President.” The journalist and historian Sam Tanenhaus has written
that Ford’s pardon enabled Nixon and his supporters to “plant the seeds of a counter-history of
Watergate,” in which Nixon “was not the perpetrator but the victim, hounded by the liberal
media.” This narrative allowed Nixon to reframe his impeachment and the congressional
investigations of his misconduct as an illegitimate “criminalization of politics.”
Since then, Trump and other demagogues have echoed Nixon’s arguments in order to deflect
investigations of their own misconduct. Meacham, who also spoke with Ford about the pardon,
says that Ford was so haunted by criticism alleging he had given Nixon a free pass that he began
carrying a typewritten card in his wallet quoting a 1915 Supreme Court decision, in Burdick v.
United States, that suggested the acceptance of a pardon implies an admission of guilt. The
burden of adjudicating a predecessor’s wrongdoing weighed heavily on Ford, and, Meacham
said, “that’s what Biden may have to wrestle with.”
Several former Trump associates worry that, if Biden does win, there may be a period of tumult
before any transfer of power. Schwartz, who has written a new book about Trump, “Dealing with
the Devil,” fears that “this period between November and the Inauguration in 2021 is the most
dangerous period.” Schwartz went on, “If Biden is inaugurated President, we’ll know that there’s
a new boss, a new sheriff in town. In this country, the President is No. 1. But, until then, the
biggest danger is that Trump will implicitly or explicitly tell his supporters to be violent.”
(Trump has already done so implicitly, having said at the first debate that the Proud Boys, an
extremist group, should “stand by.”) Mary Trump predicted that, if Trump is defeated, he and his
associates will spend the next eleven weeks “breaking as much stuff on the way out as they
can—he’ll steal as much of the taxpayers’ money as he can.”
Joe Lockhart, who served as Bill Clinton’s press secretary, suggested to me that, if Biden
narrowly wins, a chaotic interregnum could provide an opportunity for a “global settlement” in
which Trump will concede the election and “go away” in exchange for a promise that he won’t
face charges anywhere, including in New York. Lockhart argued that New York’s legal
authorities are not just lawyers but also politicians, and might be convinced that a deal is in the
public interest. He pointed out that a global-settlement arrangement was made, “in microcosm,”
at the end of the Clinton Presidency, when the independent counsel behind the Monica
Lewinsky investigation agreed to wrap things up if Clinton paid a twenty-five-thousand-dollar
fine, forfeited his law license, and admitted that he had testified falsely under oath. “So there’s
some precedent,” Lockhart said, although he admitted that such a deal would anger many
Among them would be Bauer, Obama’s White House counsel, who is now a professor at the
N.Y.U. School of Law. Bauer has argued that Presidents should be subjected to the same
consequences for lawbreaking as everyone else. “How can the highest law-enforcement officer
in the U.S. achieve executive immunity?” he said. “I understand the concerns, but, given the
lamentable condition of the justice system in this country, I just don’t get it.” Ian Bassin, who
also worked in the White House counsel’s office under Obama, and now heads the nonprofit
group Protect Democracy, said that the impetus is less to punish Trump than to discourage future
would-be tyrants. “I think Trump’s a canary in the coal mine,” he told me. “Trump 2.0 is what
terrifies me—someone who says, ‘Oh, America is open to a strongman kind of government, but I
can do it more competently.’ ”
Guessing what Trump might do if he loses (and isn’t in prison) has become a parlor game among
his former associates. In 2016, when it seemed all but certain that Trump wouldn’t be elected,
aides started preparing for what they referred to as the Trump News Network—a media platform
on which he could continue to sound off and cash in. According to a political activist with
conservative ties, among the parties involved in the discussions were Steve Bannon—who at the
time was running both the Trump campaign and the alt-right Web site Breitbart—and the
Sinclair Broadcast Group, which provides conservative television programming to nearly ninety
markets. (Sinclair denies involvement in these discussions.) Before Trump beat Hillary Clinton,
he also reportedly encouraged his son-in-law, Jared Kushner, to explore mass-media business
opportunities. After word of the machinations leaked to the press, Trump acknowledged that he
had what he called a “tremendous fan base,” but claimed, “No, I have no interest in Trump TV.”
However, as Vanity Fair recently reported, Kushner, during that preëlection period, went so far
as to make an offer to acquire the Weather Channel as a vehicle that could be converted into a
pro-Trump network. But, according to the magazine, Kushner’s offer—three hundred million
dollars—fell well short of the four hundred and fifty million dollars sought by one of the
channel’s owners, the private-equity firm Blackstone. Both Kushner and Blackstone denied the
story, but a source who was personally apprised of the negotiations told me that it was accurate.
Barbara Res, the former Trump Organization employee, and a number of other former Trump
associates believe that, if the President is defeated, he will again try to launch some sort of media
venture. A Democratic operative in New York with ties to Republican business circles told me
that Bernard Marcus—the billionaire co-founder of Home Depot and a Trump supporter—has
been mentioned recently as someone who might back a second iteration of a Trump-friendly
media platform. Through a spokesperson, Marcus didn’t rule out the idea. He said that, to date,
he has not been involved, but added, “It may be necessary going into the future, and it’s a great
idea.” Speculation has focussed on Trump’s joining forces with one of two existing nationwide
pro-Trump mouthpieces: Sinclair and the One America News Network, an anemic cable venture
notable for its promotion of such fringe figures as Jack Posobiec, who spread
the Pizzagate conspiracy theory. A Trump media enterprise would likely run pointedly to the
right of Fox News, which Trump has increasingly faulted for being insufficiently loyal. On April
26th, for instance, Trump tweeted, “The people who are watching @FoxNews, in record
numbers (thank you President Trump), are angry. They want an alternative now. So do I!”
A former Trump associate who is in the media world speculated that Trump might instead fill the
talk-radio vacuum left by Rush Limbaugh, who announced in mid-October that he has terminal
lung cancer. Neither Limbaugh nor his producers could be reached for comment. But the former
associate suggested that if Trump anchored such a show—perhaps from his golf club in West
Palm Beach, Florida—he could continue to try to rally his base and remain relevant. The former
associate pointed out that Trump could broadcast the show after spending the morning playing
golf. Just as on “The Apprentice”—and in the White House—he could riff, with little or no
preparation. Trump has been notably solicitous of Limbaugh, giving him the Presidential Medal
of Freedom, and tweeting sympathetically about his health. Limbaugh has become rich from his
show, and is estimated to be worth half a billion dollars; Trump has publicly commented on how
lucrative Limbaugh’s gig is, exclaiming in a speech last December that Limbaugh “makes, like,
they tell me, fifty million a year, and it may be on the low side—so, if anybody wants to be a
nice conservative talk-show host, it’s not a bad living.”
Res, however, can’t imagine Trump settling for a mere radio show, calling the platform “too
small.” Tony Schwartz said of the President, “He’s too lazy to do a three-hour daily show like
that.” Nevertheless, such a platform would offer Trump a number of advantages, including its
potential to make him a political power broker in the key state of Florida. (Bannon recently
forecast, to considerable skepticism, that if Trump loses the election he might run again in 2024.)
In 1997, Trump published his third book, “The Art of the Comeback,” which boasted of his
resilience after a brush with bankruptcy. But, in a recent head-to-head matchup of televised
town-hall events, Biden drew significantly higher ratings than Trump—a sign that a television
comeback might not be a guaranteed success for the President. The New York columnist Frank
Rich—a former theatre critic who has helped produce two hit shows for HBO—recently
published an essay titled “America Is Tired of the Trump Show.”
Signals from the New York real-estate world are also not encouraging. I recently asked a top
New York banker, who has known Trump for decades, what he thought of Trump’s prospects.
He answered bluntly: “He’s done in the real-estate business. Done! No bank would touch him.”
He argued that even Deutsche Bank—notoriously, the one institution that continued loaning
money to Trump in the two decades before he became President—might be reluctant to continue
the relationship. “They could lose every American client they have around the world,” he said.
“The Trump name, I think, has turned into a giant liability.” He conceded that in some parts of
the country, and in other parts of the world, the Trump name might still be a draw. “Maybe on
gas stations in the South and Southwest,” he joked.
If Trump is forced to concede the election, he will, Scaramucci expects, “go down to Florida and
build up his war chest doing transactions with foreign oligarchs—I think he’s going to these guys
and saying, ‘I’ve done a lot of favors, and so send me five billion.’ ” Nixon’s disgraced VicePresident, Spiro Agnew, who was forced to resign, in 1973, amid a corruption scandal, later
begged the Crown Prince of Saudi Arabia for financial support—while pledging to continue
fighting Zionists in America. Starting with Gerald Ford, ex-Presidents have collected enormous
speaking fees, sometimes from foreign hosts. After Ronald Reagan left office, he was paid two
million dollars to visit Japan, and half of that amount was reportedly for one speech. White
House memoirs have been another lucrative source of income for former Presidents and First
Ladies. Bill and Hillary Clinton received a combined $36.5 million in advances for their books,
and Barack and Michelle Obama reportedly made more than sixty-five million dollars for their
joint worldwide book rights. Trump has acknowledged that he’s not a book reader, and Schwartz
has noted that, during the year and a half that they worked together on “The Art of the Deal,” he
never saw a single book in Trump’s office or apartment. Yet Trump has taken authorial credits
on more than a dozen books to date, and, given that he’s a proven marketing master, it’s
inconceivable that he won’t try to sell more.
Lawrence Douglas, a professor of law at Amherst College and the author of a recent book on the
President, “Will He Go?,” predicted that Trump—whether inside the White House or out—will
“continue to be a source of chaos and division in the nation.” Douglas, who is co-editing a
textbook on transitional justice, told me that he’s uncomfortable with the notion of an incoming
Administration prosecuting an outgoing head of state. “That really looks like a tin-pot
dictatorship,” he said. He also warned that such a move could be inflammatory because, “to tens
of millions of Americans, Trump will continue to be a heroic figure.” Whatever the future holds,
Douglas doubts whether Trump could ever fade away contentedly, as many other Presidents have
done: “He craves the spotlight, both because it satisfies his narcissism and because he’s been
very successful at merchandising it.” Peaceful pursuits might have worked for George W. Bush,
but Douglas is certain of one thing about Trump’s future: “This guy is not going to take up
painting his feet in the bathtub.” ♦
Retrieved Nov. 8, 2020 at
Spectator USA
Why Trump lost
Four key reasons
Matt Mayer
Donald Trump (Getty)
Matt Mayer
November 6, 2020
8:49 PM

With the last dominoes of Georgia and Pennsylvania falling, there is now
clarity on the 2020 election cycle. Based on all of the data available at the
time and, more fundamentally, the political antennae cultivated over the last
three decades, I predicted Donald Trump would be reelected with a 305 to
233 electoral vote victory. My presidential tally was wrong. Joe Biden will
secure at least 306 electoral votes, assuming North Carolina also doesn’t fall
when final numbers are released next week.
But (there is always a but), in my defense, I was also right. When the sheer
mass of pollsters, pundits and media sages predicted a blue landslide from the
presidency down to state legislatures, I predicted America would stick with
Trump and, more importantly, the direction in which his policies were taking
our country. On that issue, the election results overwhelmingly agreed.
Outside of Trump’s loss, it looks likely Republicans will hold the Senate
despite having to defend so many seats. Republicans are making strong gains
in the House, won the sole vacant governor’s race and gained ground in state
legislatures on net. Thus, America soundly rejected the progressive agenda of
Biden, Pelosi and Schumer. A majority of Americans in a majority of states
also rejected Trump and his divisiveness. Biden’s victory came, like Trump’s
did in 2016, with thin margins in a handful of states. Biden clearly really
didn’t win as much as Trump lost.
I believe Trump lost for four key reasons.
First, Trump fatigue. Enough voters in enough key states simply had enough
of Trump and his histrionics. Yes, Trump inspired more Americans to vote
for him in 2020 then any Republican and even increased his share of the
African American, Hispanic, Muslim and Asian vote — netting a greater
share of minority votes than any Republican since 1960, but not enough to
overcome the increase in votes Biden received from Democrats and voters
tired of Trump.
Given the other election results, it is hard not to see clearly that the same
voters who rejected Trump voted for Republicans on the rest of the ticket.
That doesn’t, therefore, mean another Republican would have won the
presidency. Trump is the double-edged sword that greatly expanded the
Republican base over the last four years, but also alienated key voters from
supporting him personally. There is little evidence another candidate would
have expanded the base enough to allow other Republicans to win. The key
going forward is the Trump policy agenda without the Trump fatigue. That
makes Mike Pence a prime contender in 2024.
Next, the continued ability of the mainstream media to craft a powerful antiRepublican narrative that reaches too many Americans still is too dominant.
As I’ve noted before, imagine what the outcome of the election would have
looked like if the media coverage of Trump was just 60 percent percent
negative instead of the 90 percent negative coverage it has been for four
years. Frankly, it is stunning the presidential election was as close as it was
given the non-stop hits Trump took for four years.
From the false Russia collusion to the baseless racism allegations, no
candidate in the history of America has had to deal with such a persistently
opposition media. If Republicans want to change things, their donors should
invest billions in starting legitimate, fully-funded competing news outlets
tailored to Trump supporters and, equally critical, Republicans should stop
giving interviews to CNN, MSNBC, the New York Times, the Washington
Post and every other media outlet that slants coverage so heavily towards the
Democrats. No Republican wins because they appeared on or in any of those
outlets. Republicans need to cut-off all media entities who simply can’t be
Then, just as in 2016 when the Green party candidate Jill Stein took votes
from Hillary Clinton in key states that enabled a Trump win, the Libertarian
party candidate Jo Jorgensen deprived Trump of too many votes in key states.
Specifically, in Georgia, Pennsylvania and Wisconsin, Jorgensen’s vote total
far exceeds Biden’s margin of victory. Arizona and Nevada are close and if
North Carolina flips to Biden then Jorgensen’s total there will have hurt
Trump there, too. Those Biden victories offer from 46 to 78 electoral votes,
which means he should be thanking Jorgensen for her help in electing him
president. Libertarians can ‘celebrate’ their role in electing the candidate far
more likely to use government to infringe on their individual liberty.
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Finally, the Democrat-heavy Greater Atlanta area has become a megacity like
Greater Chicago and Great New York City that will make Georgia a
progressively harder state for Republicans to win. Because it is growing
bigger every year, the Atlanta area will only increase its sway over elections
in the coming decade. For example, in 2020 as of Thursday night, the eight
Atlanta area counties gave Biden a 639,000-vote margin compared to the
other 21 counties he won that only provided him a 140,000-vote margin. Like
Illinois and New York, Republicans largely win everywhere else, but the
margin achieved in the megacity overwhelms votes from the rest of the state.
Republicans must solve this problem or watch Georgia join the other
populated blue states making winning the presidency and US Senate more
The silver lining of this election is that Democrats and their media allies
grossly outspent Republicans and largely lost. Yes, they will control the
White House for four years, but that control will seemingly be checked by a
Republican US Senate and Justice Amy Coney Barrett is seated. Moreover,
with Eric Holder’s total failure to take over any statehouses, Republicans will
drive the redistricting and reapportionment battles in the 50 states that will
determine control of the US House starting in 2022. Fundamentally, the
Trump agenda will remain a powerful and driving force in America and the
Democrats and media won’t have Trump to kick around anymore to
undermine it.
In the long march of history, sometimes being wrong ends up being right.
Retrieved November 8, 2020 at
How Trump Lost
Peter Beinart
If he’d governed as he ran in 2016, as an economic populist, he
would likely have been reelected. Instead, he reverted to the
same old Republican playbook.
November 7, 2020
Yuri Gripas/Bloomberg
President Donald Trump attending a roundtable discussion on the Foreign Investment Risk Review
Modernization Act in the White House, Washington, D.C., August 23, 2018
The roots of Donald Trump’s reelection defeat can be traced to the early summer of 2016, when
he made a fateful bargain with his own party. In June of that year, House Speaker Paul Ryan—
who had pointedly refused to endorse Trump even after he became the de facto Republican
nominee—finally caved. Or that’s the way it appeared. “Speaker Ryan’s abject surrender makes
it official,” declared a Democratic spokesman. “The GOP is Trump’s party now.”
But that wasn’t quite right. Ryan hadn’t raised the white flag; he had made a bet. “I’ll be voting
for @realDonaldTrump,” the Wisconsin native tweeted, because “I’m confident he will help turn
the House GOP’s agenda into laws.” Ryan wagered that if he swallowed Trump’s racist
authoritarianism, Trump would enact his economic vision. For Ryan and his ideological allies—
who have devoted their careers to shredding America’s social safety net—that bet has paid off. It
has also helped cost Trump a second term.
In his campaign four years ago, Trump didn’t tell Americans that he had embraced Ryan’s takefrom-the-poor-and-give-to-the-rich agenda. To the contrary, Trump vowed not to cut Social
Security, Medicare, or Medicaid. He said he’d raise the minimum wage. He pledged to end Wall
Street’s beloved carried-interest deduction. In his election night victory speech, he promised to
“rebuild our highways, bridges, tunnels, airports, schools, hospitals.” In part because of these
claims, polls found that Americans viewed Trump as more ideologically moderate than any
Republican presidential nominee since 1972.
What Trump promised was authoritarian nationalism plus economic populism. It’s a recipe that
in other countries has proven strikingly popular. In 2019, Poland’s xenophobic and homophobic
Law and Justice party won a dominant election victory in large measure because of
its immensely popular payouts to Polish families, which, according to the World
Bank, dramatically reduced child poverty. (Law and Justice’s popularity has fallen since then, as
many Poles have revolted against its draconian efforts to outlaw abortion.) In Hungary, Viktor
Orbán has launched a New Deal-style public works program that gives hundreds of thousands of
Hungarians government jobs. In Brazil, another Trump ally, Jair Bolsonaro, has boosted his
approval ratings—particularly with poor Brazilians—by buffering them during the pandemic
with government checks. Obviously, these autocrats also use repression and propaganda to
buttress their rule. But even commentators who acknowledge their authoritarianism admit that
their economic policies enjoy substantial support.
By contrast, Trump has—in spite of his campaign promises—embraced a fiercely anti-populist
economic agenda. A Gallup poll taken the month he was inaugurated found that Americans
considered infrastructure his most important campaign promise. But a former Trump
official told The Washington Post that the White House never seriously considered making
infrastructure its top agenda item because “Paul Ryan and these guys had waited 30 years for this
once-in-a-lifetime chance to cut taxes. They were not going to let that go.” In 2017, after Ryan
and Senate majority leader Mitch McConnell shepherded a tax cut through Congress, Trump
signed it into law even though, according to the recent book Let Them Eat Tweets by political
scientists Jacob Hacker and Paul Pierson, it constituted the second-least popular piece of major
legislation of the last twenty-five years. When the Trump White House did finally propose an
infrastructure bill, congressional Republicans reportedly balked at both its price tag and the
prospect that it would increase the deficit. So the idea was shelved.
The other major congressional initiative of Trump’s first year was the effort to cancel
Obamacare—a repeal effort that, according to Hacker and Pierson, constituted the least popular
major legislation of the last quarter-century. According to one poll, the GOP’s bill enjoyed the
support of just 17 percent of Americans. Yet Trump supported that, too.
But Trump’s most self-destructive acquiescence to the congressional GOP came this fall. Last
month, after the Democratic-controlled House passed a $2.2 trillion relief bill, Trump’s Treasury
Secretary proposed legislation totaling $1.8 trillion, which would have included $1,200 payments
to individuals, higher unemployment benefits, and money for ailing businesses. After Trump said
he “would go higher,” the White House and congressional Democrats appeared close to a deal.
Then McConnell intervened. He declared that the Senate would not even vote on a package of
that size. So Trump let the negotiations collapse, even though polling from The New York
Times showed that more than 70 percent of Americans—and a clear majority of Republicans—
supported a new, $2 trillion stimulus. A Pew Research poll found that a new stimulus bill was
especially popular among lower-income Republican voters.
Why did Trump, who is often portrayed as dominating his party, cave? For the same reason he
has caved to foreign leaders: because he lacks the knowledge and self-discipline to craft a
successful negotiating strategy. Overcoming the congressional GOP’s deeply-embedded hostility
to the social safety net would have required enormous effort and tactical skill. As Harvard
political scientist Pippa Norris has detailed, based on data from the Global Party Survey, the
Republican Party is far more hostile to welfare spending than culturally conservative, and even
far-right, parties in other countries. Authoritarian populists in Poland and Hungary don’t have to
contend with the Koch brothers, who spend vast sums making Republican domestic policy safe
for plutocracy.
Even a Republican president deeply committed to economic populism would have found it
difficult to stock his administration with like-minded people since there are few major
conservative think tanks or advocacy organizations that champion higher taxes or greater
spending on health care. Trump didn’t even try. As a result, some of his key domestic policy
advisers—from Vice President Mike Pence to White House Chief of Staff Mick Mulvaney to
Health and Human Services Secretary Tom Price—were former allies of Ryan from the
Republican House.
In the more than four years since he made it, Ryan’s bet has paid off. The Trump administration
has redistributed wealth upward even more aggressively than Ronald Reagan or George W. Bush
did. But for Trump, the political consequences have been dire. When he took office, more
Americans viewed him as ideologically “moderate” than as “very conservative.” Last month,
“very conservative” exceeded “moderate” by more than fifteen points. Some of that shift may
stem from Trump’s cruel and bigoted rhetoric. But Trump’s rhetoric was just as cruel and
bigoted four years ago. In fact, his attacks on Mexican-Americans and Muslims were even
harsher in 2016 than they have been this year.
This newfound perception of Trump as ideologically extreme likely stems in large measure from
his embrace of an economic agenda that most poor and working-class Americans loathe. In 2016,
according to exit polls, Trump lost voters who earned under $50,000 by roughly ten points; this
year, he lost them by fifteen points. In 2016, voters earning between $50,000 and $100,000
favored him by four points; this year, that flipped to a thirteen-point deficit.
Among the richest Americans—those earning over $100,000—Trump substantially improved his
margin of victory over 2016. But in blue-collar America, his support crumbled. Some of that
shift may be because of Trump’s opponent, but much of it is because of Trump himself. Except
perhaps on trade, he turned out not to be the economic populist he vowed to be in 2016.
For years now, commentators have wondered when the Republican Party would return to
normal. By “normal,” they generally mean well-mannered, not openly racist, and not openly
hostile to the rule of law. They mean the Republican Party as defined by people like Paul Ryan.
But that Republican Party, for all its supposed decorum, has for decades pushed policies that
threatened the wellbeing and economic survival of many Americans.
Four years ago, Trump won the presidency in part because he pledged to end that assault.
Instead, he escalated it, even during the worst economic downturn since the Depression. Donald
Trump didn’t lose reelection because he changed the Republican Party too much. He lost
because he changed it too little.
Retrieved November 8, 2020 at
The New Yorker Magazine
May 11, 2020 Issue
How Greenwich Republicans
Learned to Love Trump
To understand the President’s path to the 2020 election, look at what
he has provided the country’s executive class.
By Evan Osnos
May 3, 2020
In Greenwich, Trump’s rise was less a hostile takeover than a joint venture. “He says everything
I think,” a Republican said.
Prescott Bush, the father and grandfather of future Presidents, was the eight-time club champion
on the golf course at the Round Hill Club, one of eight country clubs in Greenwich, Connecticut.
Bush was a staunch believer in standards; he required his sons to wear a jacket and tie for dinner
at home. He was tall, restrained, and prone to righteousness; friends called him a “Ten
Commandments man.” In the locker room at Round Hill, someone once told an off-color joke in
front of his fourteen-year-old son, George H. W. Bush, and Prescott stormed out, saying, “I don’t
ever want to hear that kind of language in here again.”
In Greenwich, which had an unusually high number of powerful citizens, even by the standards
of New York suburbs, Prescott Bush cast a large shadow; he was an investment banker, the
moderator of the town council, and, from 1952 to 1963, a United States senator. In Washington,
he was President Eisenhower’s golf partner, and the embodiment of what Ike called “modern
Republicanism.” Prescott wanted government lean and efficient, but, like Nelson Rockefeller,
the New York governor whose centrism inspired the label Rockefeller Republican, he was more
liberal than his party on civil rights, birth control, and welfare. He denounced his fellowRepublican Joseph McCarthy for creating “dangerous divisions among the American people”
and for demanding that Congress follow him “blindly, not daring to express any doubts or
disagreements.” Bush could be ludicrously aristocratic—he had his grandchildren call him
Senator—but he believed, fundamentally, in the duty of government to help people who did not
enjoy his considerable advantages. He supported increasing the federal minimum wage and
immigration quotas, and he beseeched fellow-senators, for the sake of science, education, and
defense, to “have the courage to raise the required revenues by approving whatever levels of
taxation may be necessary.”
Long after Bush died, in 1972, his family stayed central to the community of Greenwich
Republicans. His son Prescott, Jr., known as Pressy, served as the chairman of the Republican
Town Committee; alumni of the Bush Administrations still live around town. Each year, the
highest honor bestowed by the Connecticut Republican Party is the Prescott Bush Award.
When Donald Trump ran for President, he was hardly a natural heir to the Greenwich Republican
tradition. In the eighties, he bought a mansion on the town’s waterfront, but he did not often
observe the prim Yankee ethic inscribed on the Greenwich coat of arms: fortitudine et
frugalitate—courage and thrift. Locals were embarrassed by the house’s gilded décor, and, after
he and his wife Ivana divorced, she sold it. When George H. W. Bush called for a “kinder,
gentler nation,” Trump responded, “If this country gets any kinder or gentler, it’s literally going
to cease to exist.” In early 2016, even before Trump was asserting his right to “locker-room
talk,” he was denounced in Greenwich Time, the town’s daily newspaper, by Leora Levy, a
prominent local fund-raiser. “He is vulgar, ill-mannered and disparages those whom he cannot
intimidate,” she wrote. Levy—the latest winner of the Prescott Bush Award—was lending her
support to Prescott’s grandson Jeb Bush, the former governor of Florida.
But not everyone in Greenwich was excited about Jeb. Jim Campbell was the chairman of the
Republican Town Committee. The Campbells, like the Bushes, had deep roots in town. Jim
prepped at Exeter and graduated from Harvard and Harvard Law School, before working in
Europe and returning home as a real-estate executive. On a fall evening, Campbell attended a
reception for Jeb Bush at the Belle Haven Club, a private tennis-and-boating club overlooking
Long Island Sound. Jeb was expansive and mild, which struck Campbell as precisely wrong for
the political moment: “He gave a whole talk about a woman named Juanita in South Florida, and
how ‘immigration is love,’ and I just looked at the people I came with and said, ‘Does he think
he’s already the nominee? He’s running in a tough Republican primary, and just because we’re at
the Belle Haven Club doesn’t mean we’re all voting for him.’ ”
At home one night, watching television, Campbell happened on a Trump rally in Iowa. “I’m not
a hard-core conservative—I’m a Republican from Greenwich,” Campbell said. “But I listened,
and he had that line that he would use: ‘Folks, we either have a country or we don’t.’ And I felt
the chill—like Chris Matthews with the little Obama zing up the leg. I’m, like, ‘Oh, my God, this
is a really good line.’ ” To Campbell, Trump was describing immigration in ways that resonated:
“Could somebody finally say that we’re allowed to enforce the law at the border without being
called a racist? I lived in Switzerland for ten years. Do you think I was allowed to go around
without a passport?”
Campbell tapped out a text message to a friend: “Trump live – can’t turn the channel.
Unbelievable. I don’t think any R can beat him.” Campbell watched the rally for forty-five
minutes. “He was mesmerizing,” he said. Not long afterward, he saw a Republican debate in
which Trump described the invasion of Iraq as a mistake. For Campbell, the acknowledgment
came as a catharsis. “Of course it was a big, fat mistake,” he told himself. “He says everything I
In early 2016, Campbell attended a dinner for Republicans at the Delamar Greenwich Harbor, a
Mediterranean-themed boutique hotel that is popular with local finance executives. After a
dinner speaker mocked the notion of building a wall and imposing tariffs, Campbell raised his
hand: “I said, ‘With all due respect, why is it that we’re not allowed to support a candidate who
supports the things that you just ticked off?’ ” Campbell knew that his question would cause a
stir, but he had decided that it was time “to let everybody know who I was supporting.” When
the event was over, he discovered that he was not alone: “I had four guys make a beeline for me,
Wall Streeters, all saying, ‘What can we do? Can I sign up? Are you organizing?’ ”
In February, 2016, with Jeb still vying for the nomination, Campbell endorsed Trump. “I just
think there’s a lot of people supporting Donald and don’t want to say so,” he told a local reporter.
That spring, as Connecticut Republicans prepared to vote in their primary, political observers
predicted that John Kasich, the moderate governor of Ohio, would prevail in towns and cities
from Greenwich to Fairfield—a stretch of American bounty known as the Gold Coast. Instead,
Trump largely dominated the region.
Four years later, Trump signs are still scarce in Greenwich (population 62,600), but his
supporters are easy to find. There is the first selectman—the local equivalent of mayor—and the
chairman of the Greenwich finance board, as well as an ardent backer who serves in the state
House of Representatives. Some local Republicans helped fund Trump’s Inauguration, and some
joined his White House, including Linda McMahon, the former professional-wrestling executive
who headed the Small Business Administration, and Hope Hicks, Trump’s longtime
communications adviser. (She once captained the Greenwich high-school lacrosse team.) Others
in town have abandoned their objections to Trump. Leora Levy, who called him vulgar in the
local paper, took to applauding his “leadership” and quoting him on Twitter, where she adopted
some of his rhetorical style. “AMERICA WILL NEVER BE A SOCIALIST COUNTRY!!!” she posted. “WE
ARE BORN FREE AND WILL STAY FREE!!!” Last fall, Trump nominated her to be the American
Ambassador to Chile.
How did America’s country-club Republicans, the cultural descendants of Prescott Bush, learn to
love Donald Trump? They don’t have much in common with the clichéd image of his admirers:
anxious about losing status to minorities, resentful of imperious élites, and marooned in places
where life expectancy has fallen. But the full picture has never been that simple. As early as
May, 2016, exit polls and other data showed that Trump supporters earned an average of
seventy-two thousand dollars a year, while supporters of Hillary Clinton earned eleven thousand
dollars less. Two-thirds of Trump’s supporters had incomes higher than the national median—
sometimes, as in Greenwich, much higher.
I grew up in Greenwich, on Round Hill Road, not far from the club where Prescott Bush stormed
out of the locker room. My great-grandparents Albert and Linda Sherer moved to town from
Chicago in 1937. Albert was a Republican who worked in advertising for the National Biscuit
Company, and Linda raised their two children. They were renters until 1968, when they bought a
white Colonial with a wide lawn. The house passed down through the generations, and, when I
was nine years old, my parents moved the family from Brooklyn to Greenwich, into a world of
uncountable advantages. In 1994, I graduated from Greenwich High School, which is the rare
public school that has a championship water-polo team and an electron microscope. (It was a
donation, obtained by an award-winning science teacher.)
People around town have never much cared for caricatures of the place—the starchy patricians,
the chinless wonders, the history of exclusion—even when there is truth in them. For decades,
many African-Americans and Jews were prevented from buying homes. In 1975, protesters came
to town with signs reading “COCKTAIL BIGOTS” and “SHARE THE SUMMER,” because Greenwich
barred nonresidents from a public beach—a restriction that lasted until the state Supreme Court
overturned it, in 2001. Nobody pretends that bigotry has vanished, but these days the town has
more diversity than outsiders expect. Thirty-eight per cent of its public-school students are
minorities, mostly Latino; in some elementary schools, at least half the students qualify for free
or reduced-price lunch. Many of their parents work in local service jobs, bearing high rents and
expenses in order to access some of the country’s best public schools. Frank Farricker, a realestate developer and a Democratic activist, said, “I tell everybody that Greenwich only
discriminates on the basis of one color: green.”
The seacoast of Fairfield County has always been one of America’s most affluent places, but in
recent decades it has sprinted ahead of the rest of the country. In 2016, according to federal
estimates, it was the wealthiest metropolitan area in the United States, outstripping the oil
country of Midland, Texas, and the technology hub of San Francisco. Even though a string of
tycoons have fled Connecticut in search of lower taxes, the latest Forbes ranking of the world’s
billionaires lists fifteen of them in the “Greater Greenwich Area,” led by Ray Dalio, the founder
of the hedge fund Bridgewater, who is worth an estimated eighteen billion dollars.
From afar, it is easy to misread the politics of the place: like much of America’s coasts, the Gold
Coast has swung left, culturally and politically, since the days of Prescott Bush. The largest share
of voters in Greenwich today are unaffiliated; Republicans still hold an edge over Democrats, but
the margin is less than four thousand registered voters. In 2016, nobody was surprised that
Clinton beat Trump in Greenwich, fifty-seven per cent to thirty-nine. But that portrait—of liberal
cosmopolitans appalled by Trump—obscures a potent element of American politics: the
executive class of the Republican Party. Its members are wealthier, more conservative, and more
politically active than their forebears, in ways that have helped Trump reach the White House,
survive impeachment, and fortify his bid for reëlection during the anguish of the coronavirus
pandemic. Understanding how he retains the overwhelming support of Republicans requires an
accounting of not only what he promised Americans at the bottom but also what he provides
Americans at the top.
The story of Trump’s rise is often told as a hostile takeover. In truth, it is something closer to a
joint venture, in which members of America’s élite accepted the terms of Trumpism as the price
of power. Long before anyone imagined that Trump might become President, a generation of
unwitting patrons paved the way for him. From Greenwich and places like it, they launched a set
of financial, philanthropic, and political projects that have changed American ideas about
government, taxes, and the legitimacy of the liberal state.
The former congressman Christopher Shays is a moderate Republican who was elected eleven
times to represent the Gold Coast, from 1987 to 2009. Now conservatives mock him as a RINO—
a Republican in name only. “When Sean Hannity calls someone like me a RINO, I want to punch
him in the nose,” Shays told me. “I got elected as a Republican for thirty-four effing years, and
Hannity has never gotten elected for anything.” When Shays talks to former staff and
constituents in Connecticut, he has come to recognize the delicate language of accommodation:
“I was talking to a guy I know well, after some pathetic thing that Trump did, and his response
was ‘Yes, but he’s selecting the right Supreme Court Justices.’ I started to laugh at him, because
I know for a fact that’s a minor issue for him.” Shays believes that many Americans quietly share
Trump’s desire to reduce immigration and cut social-welfare programs for the poor. “He’s saying
what people think, and they appreciate that,” Shays said. “But not many are going to admit that’s
why they support him.”
When it comes to the essential question—will Trump get reëlected?—the answer rests heavily on
a persistent mystery: how many Americans plan to vote for him but wouldn’t say so to a
pollster? In Greenwich, Edward Dadakis, a corporate insurance broker who has been involved
with Republican politics for fifty years, told me that many of his friends are “below the radar
screen.” He went on, “In a sense, I’m one of them. I’m out there in the public domain, so people
know where I stand, but in 2016, for the first election ever, I did not put a bumper sticker on my
car.” He worries how strangers will react. He said, “I still have two ‘Make America Great Again’
hats at home, wrapped in plastic.”
The southern panhandle of Connecticut is cradled between the gray-blue waters of Long Island
Sound and the wooded border of New York State. In politics and in culture, it’s a mashup of
New England and New York, a place settled by Puritans who agonized over what the historian
Missy Wolfe calls “the proper balance between their flock’s economic success and the level of
success that they deemed would offend God.” Long after the Puritans were gone, the tension
remained in a seesawing battle between the Brahmin and the buccaneer, service and profit,
restraint and greed. For much of the twentieth century, the Brahmin had the advantage.
In 1927, Owen D. Young, a Greenwich resident who was the first chairman of General Electric,
gave a speech at Harvard Business School, in which he scolded businessmen who “devise ways
and means to squeeze out of labor its last ounce of effort and last penny of compensation.” He
encouraged them instead to “think in terms of human beings—one group of human beings who
put their capital in, and another group who put their lives and labor in a common enterprise for
mutual advantage.” Rick Wartzman, a longtime head of the Drucker Institute and a historian of
corporate behavior, told me, “This really was beyond rhetoric. We were much more of a ‘we’
culture than an ‘I’ culture.” On Young’s watch, G.E. became one of the first American
companies to give workers a pension, profit-sharing, life insurance, medical coverage, loans, and
housing assistance.
Greenwich was home to a community of progressive journalists and authors, including Lincoln
Steffens, Anya Seton, and Munro Leaf. But it was most popular with executives—at General
Electric, Texaco, U.S. Tobacco—who were fleeing high income taxes in New York. Other
residents served as their investment bankers, a cohort that was, by today’s standards, almost
unrecognizably buttoned-down. By and large, local Republicans had come to accept the
expansion of government under Franklin D. Roosevelt and were concerned mainly with avoiding
excesses and insolvency. Showing off your money was déclassé. At Morgan Stanley, executives
competed to see who could wear the cheapest watch. “Some of the wealthiest people went
around dressed like gardeners,” a friend of mine who grew up in Darien recalled.
One of America’s most powerful capitalists, Reginald Jones, who became G.E.’s chairman and
C.E.O. in 1972, lived in a modest brick Colonial in Greenwich. His daughter, Grace Vineyard,
told me, “He asked my mom, ‘Do you want anything more?’ And she said, ‘Why would we want
anything more?’ ” Leo Hindery worked for Jones as a junior executive. “I earned fifteen
thousand six hundred dollars when I got out of Stanford, and Reg’s salary was two hundred
thousand dollars,” Hindery said. “G.E. was the preëminent company in America, and the C.E.O.
was making twelve or thirteen times what I did.” According to the Economic Policy Institute,
that ratio wasn’t unusual: in 1965, the C.E.O. of an average large public company earned about
twenty times as much as a front-line worker. Today, that figure is two hundred and seventy-eight
The moderate consensus was always shakier than it looked, and by the mid-sixties it was
gyrating out of control. In 1955, William F. Buckley, Jr., had established his magazine National
Review on the principle that government exists only “to protect its citizens’ lives, liberty and
property. All other activities of government tend to diminish freedom and hamper progress.” It
was the opening shot of the modern conservative movement, though, on the whole, liberal
intellectuals did not regard it as a serious challenge. In 1963, John Kenneth Galbraith, the liberal
economist and adviser to the Kennedys, mocked the modern conservative for being engaged in
“one of man’s oldest, best financed, most applauded, and, on the whole, least successful
exercises in moral philosophy. That is, the search for a truly superior moral justification for
In Greenwich, however, some people were seized by the new conservatism. J. William
Middendorf II was a Harvard-educated investment banker who had served on the town council
with Prescott Bush, his friend and neighbor. “I sold him a piece of land at the foot of my
property,” Middendorf told me. When he retired to his porch in the evening, he could hear the
Bushes singing Yale songs in their back yard. But, beneath the similarities, Middendorf had
adopted a strikingly different ideology; he had become, in his words, a “disciple” of the
libertarian movement, enthralled by Friedrich Hayek and Joseph Schumpeter. He condemned
Eisenhower’s moderates for regarding government as “a working tool that should be used to
shape society.” Instead, he wrote, “I believe that society is shaped by individuals.”
Middendorf wanted to push libertarianism into mainstream politics, and he found a vehicle
in Barry Goldwater, the fiery Arizona senator. Goldwater, the heir to a department-store fortune
in Phoenix, ran for President in 1964, fuelled by what he described as “my resentment against the
New Deal.” Goldwater’s campaign was a backlash against liberalism—the antiwar movement,
civil rights, welfare—but also against moderate Republicans. Nelson Rockefeller was a
“cardboard candidate,” Middendorf told me. “He could speak for an hour, but I honestly could
not remember a single word he ever said.” Middendorf became Goldwater’s campaign treasurer,
raising money from other well-to-do dissidents of the East Coast establishment. “He was
obviously out of the mainstream, and we had an uphill battle,” he said.
They prevailed that summer, at the Republican National Convention, in San Francisco.
Rockefeller made a desperate last attempt for relevance: from the lectern, he denounced the
advent of a “radical” right-wing element within the Party, in the hope that the moderates would
rise up and resist. Instead, the hall erupted in boos. Jackie Robinson, the black baseball star and
an avatar of integration among Republicans, heard the catcalls and felt, as he said later, like “a
Jew in Hitler’s Germany.” Middendorf, who was also in attendance, received Rockefeller’s
denunciation as an affirmation. “He was talking about me and my friends,” he wrote, in
“Potomac Fever,” his political memoir.
In the general election, Goldwater lost—spectacularly—to Lyndon Johnson. But his brand of
libertarian, antitax absolutism found a fervent audience among American executives who were
confronting an alarming change: after a quarter century of relentless growth, American profits
were declining. Japan and Western Europe, finally rebuilt after the Second World War, were
formidable new competitors; the Arab oil shock of 1973 triggered the longest recession since the
thirties. Moreover, the environmental and consumer-protection movements had hastened new
regulations, on products ranging from flammable fabrics to cigarettes and bank loans.
Executives felt besieged. “They decided regulation was mostly to blame,” the historian Rick
Perlstein writes in his forthcoming book, “Reaganland.” In Perlstein’s telling, “the denizens of
America’s better boardrooms, who had once comported themselves with such ideological
gentility, began behaving like the legendary Jacobins of the French Revolution. They declared
war without compromise.” Back home in Greenwich, Middendorf—who went on to work in the
Nixon, Ford, and Reagan Administrations—gloried in having vanquished the moderates. He
wrote, “We created the conditions that put conservative Republicans back in power after more
than thirty years of domination by the liberal eastern establishment—the so-called ‘Country
Club’ Republicans.”
Ashort drive from the Round Hill Club, in a Georgian manor overlooking a lake, lived Lee and
Allie Hanley, who were early converts to the conservative movement. Lee had graduated from
St. Paul’s and from Yale, where he played polo, squash, and soccer, and he had taken over
Hanley Co., his family’s brick-and-oil business. He was a bon vivant, with a fondness for
salmon-colored slacks, and a ready checkbook for political ventures. “Very warm and engaging,”
a Greenwich friend said. “A collector of curiosities, a Renaissance man at sort of a superficial
level. More of a gut player who wanted to be in the game.” Allie was a devout Christian with a
keen interest in politics. The 1980 Republican primary was shaping up to be a contest between
the old Republican Party and the new—George H. W. Bush, a Washington insider known around
town as Poppy, versus Ronald Reagan, the conservative governor of California. On that question,
the Hanleys broke with their neighbors in Greenwich. “For us, it was never Bush country,” Allie
told me recently. “It was always Reagan country.”
Roger Stone, who was Reagan’s campaign director for the Northeastern states, recalled that most
people in Greenwich recoiled from his candidate: “They thought, Reagan, oh, my God, he’s
another Goldwater. He has no chance in the general election. He’s a cowboy-movie actor.”
(Stone, who later became a Trump confidant, spoke to me last year, before he was convicted of
lying to Congress during Robert Mueller’s investigation.) “Hanley was the only high Wasp we
had,” Stone continued. “All the ‘right’ people were for Poppy.”
The Hanleys, hoping to spread their enthusiasm in Greenwich, agreed to host a reception at their
home. But, when they met Reagan to discuss the plans, over lunch at the Pierre Hotel, Allie saw
a problem. “He had on a brown tie, and it was ghastly,” she told me. “When you go to a different
part of the country, the most important thing you need to do is dress like they do. They feel more
comfortable talking to you. So I ran to Bloomingdale’s, and I bought four ties.” When the
Reagans turned up for the party, Allie said, “Here’s a gift for you! Go upstairs and freshen up.”
Reagan came back down a few minutes later, and the offending tie had been replaced by her gift.
“He wore it on all the posters after that,” she said.
Stone and Lee Hanley adopted an approach that uncannily prefigured Trump’s electoral strategy:
they built a coalition of conservative élites and the white working class. Hanley introduced Stone
to small-business owners in Greenwich, many of them Italian-American—“mining for Catholic
votes,” as Stone called it. “Lee was very well connected with the merchants in town—the grocer,
the butcher,” Stone said. “He could talk to anybody. He was not stuffy like some Wasps.”
Hanley told Stone before one visit, “We’re going to have to drink some espresso, but we can get
them.” The strategy worked; in the Connecticut primary, Reagan beat Bush in the Bush-family
stronghold of the southern panhandle. In 1984, Reagan rewarded Hanley by nominating him to
the board of the Corporation for Public Broadcasting. Two years later, he became the chairman.
In the next three decades, Hanley and other wealthy conservatives—Richard Scaife, John
Olin, the Koch brothers—helped train a generation of Republicans in Congress to adhere to
ideological orthodoxy. Hanley made a string of historic political investments. He saved Regnery,
America’s most prominent conservative book publisher, with a crucial infusion of cash. He
helped found the Yankee Institute for Public Policy, the Connecticut affiliate of a network of
think tanks that advocate for low taxes and small government. He became the principal backer of
a political consulting firm formed by Stone and two other young Reaganites, Charlie Black
and Paul Manafort. “We had the credentials and the potential business and all that, but we didn’t
have any money,” Black told me. “Lee was a good friend, so we approached him.” Black,
Manafort & Stone, as they called themselves, became pioneering lobbyists, known for their
brazen use of what Manafort described as “influence peddling.” Clients included Rupert
Murdoch’s News Corp. and a young real-estate developer named Donald Trump.
By the end of the century, the courtly politics of Prescott Bush were gone, a change accelerated
by the decisions of his son George H. W. Bush. George had inherited his father’s restraint—at
school in Greenwich, he was nicknamed Have-Half, for his willingness to share—and also the
family tradition of public service. But, running for President in 1988, Bush unleashed his
brawling campaign manager Lee Atwater on the governor of Massachusetts, Michael Dukakis.
Atwater vowed to “strip the bark off the little bastard.” In the most searing moment, a politicalaction committee linked to the Bush campaign paid for a television ad blaming Dukakis for the
case of Willie Horton, a convict who had committed rape during a furlough from a
Massachusetts prison. The ad crudely exploited white fears, showing pictures of Horton, who
was African-American, while a narrator spoke of kidnapping, rape, and murder. Atwater denied
any involvement in the ad, but Bush recognized the power of the rhetoric, and took to
mentioning Horton almost daily on the stump. Atwater boasted that he would make Horton
“Dukakis’s running mate.”
Not long before Atwater died, in 1991, he apologized to Dukakis for the “naked cruelty” of that
campaign. But the Willie Horton strategy was the forerunner of a more savage era in American
politics—of Swift Boat attacks on a war hero; of the racist birther fiction against America’s first
black President—and it pushed candidates to avoid looking weak by advancing tough-on-crime
policies that both parties now view as devastating for low-income and minority Americans.
In the end, Bush was “a gentleman, but he was a politician, too,” his biographer Jon
Meacham wrote. For all Bush’s decency, he had decided early on that, in order to serve, he
needed to win. In a tape-recorded diary entry near the end of the 1988 campaign, Bush told
himself, “The country gets over these things fast. I have no apologies, no regrets, and if I had let
the press keep defining me as a wimp, a loser, I wouldn’t be where I am today.”
In the early years of this century, the economic divisions that would come to define America in
the age of Trump became evident on the lush back roads of Greenwich, in a sign so subtle that it
was easy to miss. Many of the new estates going up were no longer surrounded by the simple
stone walls, stacked to the height of a farmer’s hip, that crossed the New England landscape.
Instead, the builders introduced a more imposing barrier: tall, stately walls of chiselled stone,
mortared in place.
The fashion for higher walls had little to do with safety; Greenwich has one of the lowest crime
rates in America. To Frank Farricker, who served on the town’s planning-and-zoning
commission, they symbolized power and seclusion. “Instead of building two or three feet high,
people got into six-footers—the ‘Fuck you’ walls,” he said. When nearby municipalities noticed
the trend, they treated it like an invasive species; they rewrote zoning rules to prevent the spread
of what stonemasons took to calling “Greenwich walls.”
The walls were products of one of the most extraordinary accumulations of wealth in American
history. In much of the country, the corporate convulsions of the seventies had entailed layoffs,
offshoring, and declining union power, but on Wall Street they inspired a surge of creativity.
Since the seventeen-hundreds, Wall Street had focussed mostly on funnelling American savings
into new businesses and mortgages. But, in the last two decades of the twentieth century,
financiers and economists opened vast new realms of speculation and financial engineering—
aggressive methods to bet on securities, merge businesses, and cut expenses using bankruptcy
laws. U.S. stock markets grew twelvefold, and most of the gains accrued to the wealthiest
Americans. By 2017, Wall Streeters were taking home twenty-three per cent of the country’s
corporate profits—and home, for many of them, was Connecticut.
The Internet allowed financiers to work from anywhere, so some escaped New York’s higher
taxes by relocating their offices closer to where they lived. Newspapers took to calling
Greenwich the “Hedge Fund Capital of the World.” The dealmakers earned vastly more than the
industrial executives they had replaced. In 2004, Institutional Investor reported that the top
twenty-five hedge-fund managers earned an average of two hundred and seven million dollars a
Nine of those top managers lived or worked in Greenwich, led by Edward Lampert, who in 2004
earned an estimated $1.02 billion after orchestrating the merger of Kmart and Sears. Lampert
was not one to dress like a gardener; just offshore, he docked his yacht, a two-hundred-andeighty-eight-foot vessel that he had named Fountainhead, for Ayn Rand’s individualist fable.
(Trump has said that he identifies with the book’s hero, Howard Roark, a designer of skyscrapers
who declares, “I do not recognize anyone’s right to one minute of my life. . . . No matter who
makes the claim, how large their number, or how great their need.”) So much individual wealth
accumulated in southern Connecticut that tax officials took to monitoring the quarterly payments
of a half-dozen of the richest taxpayers, because their personal earnings would affect how much
the entire state was able to spend on public services.
Around town, Morgan Stanley executives no longer competed to wear the cheapest wristwatch.
(The current chairman and C.E.O., James Gorman, is celebrated on watch-enthusiast blogs for a
rare Rolex that can sell for seventeen thousand dollars.) Jack Welch, who succeeded Reginald
Jones at G.E., retired in 2001 with a record severance package of more than four hundred million
dollars. One of Jones’s friends, the investor Vincent Mai, was dismayed that many business
leaders put short-term interests ahead of long-term vision. “The culture changed into grabbing as
much as you can, as quickly as you can,” Mai, the founder and chairman of the Cranemere
Group, told me. “Restraint just seems to have gone out the window.”
The money physically redrew Greenwich, as financiers built estates on a scale once favored by
Gilded Age railroad barons. The hedge-fund manager Steven A. Cohen paid $14.8 million in
cash for a house, then added an ice rink, an indoor basketball court, putting greens, a fairway,
and a massage room, ultimately swelling the building to thirty-six thousand square feet—larger
than the Taj Mahal. In a final flourish, Cohen obtained special permission to surround his estate
with a wall that exceeded the town’s limits on height. It was nine feet tall.
When the tide began to turn against Wall Street, you could follow it from my family’s front door.
Up and down Round Hill Road, neighbors became known for one imbroglio after another. If you
took a right turn out of our driveway, you could wander by the stone Colonial house of Walter
Noel, a money manager with a gracious Nashville accent, who funnelled billions of his clients’
dollars to the grifter Bernie Madoff. (Noel claimed that he, too, was duped.) If you turned left,
you reached the estate of the hedge-fund manager Raj Rajaratnam, who once celebrated his
birthday by flying in Kenny Rogers to sing “The Gambler” over and over, until Rogers finally
refused. In 2009, Rajaratnam was arrested as part of a stock-cheating case that the F.B.I. called
Operation Perfect Hedge. He was given a sentence of eleven years in prison, the longest ever for
insider trading. Eventually, so many neighbors were ensnared in financial scandals that a local
blogger nicknamed our street Rogues Hill Road.
In truth, nobody was shocked that the vast new fortunes of the Gold Coast contained the seeds of
financial catastrophe. In the run-up to the 2008 crisis, William Wechsler was a managing director
at Greenwich Associates, a consulting firm, where he saw financiers taking ever-larger risks.
Historically, the bylaws of the New York Stock Exchange had required trading firms, such as
Goldman Sachs, to be private partnerships. “When it was time for you to go, you sold your share
to the next generation,” Wechsler told me. “It was culturally acceptable to get to a certain level
of success and retire happy.” But, by 1999, the rules had changed, the big banks had become
public companies, and investors expected large returns. Hedge funds and other firms made huge
bets, in pursuit of dramatic windfalls. Instead of directing most of their capital to funding
businesses that hired people and made things, the financiers in New York and Connecticut had
become an economy unto themselves. “Every year that goes by, more and more of the added
value in our society goes toward capital, and less and less toward labor,” Wechsler told me.
“What you end up with is a very unstable society.”
On top of that, Wall Street was hiring lobbyists to dismantle regulations that protected the
country from an economic fiasco. In some cases, Greenwich residents led the big banks that
lobbied for destructive changes. John Reed was a co-chairman of Citigroup, and William B.
Harrison, Jr., was the chief executive of JPMorgan Chase. Their banks were two of the largest
contributors to Senator Phil Gramm, the Texas Republican who engineered a ban on the
regulation of over-the-counter derivatives. Later, the government’s official autopsy of the
collapse called that ban “a key turning point in the march toward the financial crisis,” because
“derivatives rapidly spiraled out of control and out of sight.”
As the economy quaked, the shock waves reverberated through politics. The Tea Party
movement raged against Obama, taxes, and social-welfare programs, helping Republicans to
greater gains in the 2010 midterms than in any congressional election in six decades. Even in
Greenwich, where people are not quick to hoist placards, Tea Party activists protested in front of
Town Hall, and the first selectman Peter Tesei, the town’s top elected official, joined in. “Liberty
has contracted today because the role of government has expanded,” he told the crowd. (Tesei,
like many of his ideological allies, later pledged to support Trump.)
The sentiment was a familiar one—even the Romans resented their taxes—but Greenwich was
not traditionally known for absolutism on the subject. In the nineteen-eighties, Lowell Weicker, a
Greenwich Republican who had served as first selectman and gone on to the U.S. Senate,
became known in Washington for blocking Reagan’s attempts to cut spending on health and
education. In 1991, after Weicker became governor, he imposed Connecticut’s personal income
tax, which was so unpopular that protesters cursed and spat at him. In a speech that fall, he said,
“Respect—if not reëlection—comes from speaking the truth.”
But, to some in the current generation, especially Greenwich’s new concentration of libertarians,
a fiercer resistance to taxes and to government was a matter of moral principle. Cliff Asness, a
billionaire who runs AQR Capital Management, was among the most vocal. When Governor
Andrew Cuomo, of New York, discussed raising taxes on hedge funds, Asness tweeted that he
was a “flat out lying demagogue,” who was trying to run a “gulag not a state.” Around town, the
expectation that a person of substantial means might pay substantial taxes no longer held sway.
That became especially clear in 2013, when Thomas Foley, a Greenwich private-equity investor,
ran for governor. He owned a yacht, a number of vintage cars, two British fighter jets, and a
house that Greenwich Time likened to “the Hogwarts castle.” But, on tax returns that he showed
reporters, he had claimed so many investment losses and alimony payments that his federal taxes
amounted to six hundred and seventy-three dollars that year. (Foley lost the race.)
Charles Rossotti, a Republican businessman who served as the commissioner of the I.R.S. from
1997 to 2002, has estimated that sophisticated tax ploys and shelters cause ordinary citizens to
pay an extra fifteen per cent in taxes each year. Brooke Harrington, an economic sociologist at
Dartmouth, told me, “Some of that shortfall just never gets made up. Those are roads that don’t
get improved, public transport that doesn’t get built, schools that don’t get fixed.” Connecticut
has the richest one per cent of any state, but, according to several studies of crumbling
infrastructure, its roads are among the worst in the country.
Harrington said, “For an earlier generation, even if your heart wasn’t in it, you’d say, ‘I’ve got to
join the local charity board, to project that I deserve this wealth.’ ” The current generation,
instead of focussing on the local charity board, prefers targeted private philanthropy, bypassing
public decisions on whom to help and how. “The underlying massive change is that wealth no
longer needs to justify itself—it is self-justifying,” Harrington said. “I look back, and I think,
That’s when we gave up on being a ‘we.’ ”
In the political ferment brought on by the Tea Party and the resistance to Obama, conservative
donors expanded their influence. The Hanleys became funders of Turning Point USA, a
nonprofit, founded in 2012, that promotes conservatism in high schools and colleges. More
important, Allie Hanley helped its founder, Charlie Kirk, meet other donors. “Allie Hanley
opened the entire southern corridor for us,” he wrote later. Kirk is now a conservative celebrity
and the chairman of Students for Trump, a campus political network. In recent years, Turning
Point has faced multiple controversies. Some student governments have sought to ban it for
interfering in their elections; staff and members have been discovered making racist comments.
Last year, a video showed Riley Grisar, the head of a Turning Point chapter in Nevada, saying
“white power,” with his arm wrapped around a woman who said, “Fuck the niggers.” (Grisar was
removed from the organization.)
Lee Hanley used his fortune to elevate candidates on the right wing of the Republican Party. In
2014, he donated some three hundred and fifty-seven thousand dollars; the money went to stars
such as Ted Cruz, but also to oddball outsiders like Chris McDaniel, a Mississippi state
lawmaker and former talk-radio host who was trying to unseat the incumbent senator, Thad
Cochran. McDaniel lost, but his campaign themes were a preview of politics to come; before
Trump was popularizing anti-immigrant rhetoric, McDaniel was pledging to block increases in
residency permits and work visas. (When McDaniel ran for the Senate again, in 2018, he
embraced a blunter racial message, arguing to preserve a Confederate emblem on the state flag.)
But none of Hanley’s political investments would pay off as well as an obscure project for
which Steve Bannon, Trump’s former strategist, calls him one of the nation’s “unsung heroes.”
Not long after Mitt Romney lost to Obama, in 2012, Hanley commissioned a pollster named
Patrick Caddell to investigate why conventional Republican candidates were underperforming.
Caddell had made his name advising Jimmy Carter, but he had broken with Democrats and
begun appearing frequently on Fox News. As he and Hanley discussed the project, both
suspected that the electoral returns suggested a deep frustration with the status quo. “I said, ‘I
think something’s happening in the country,’ ” Caddell recalled. “Lee said, ‘You know, I think
something may be, too. I want you to go out and just find out.’ ” Caddell’s polls quickly
suggested that the “level of discontent in this country was beyond anything measurable.”
In 2013, Hanley asked Caddell to show his findings to Bannon, and to another patron, the hedgefund billionaire Robert Mercer. They huddled over the data during a conservative conference in
Palm Beach. The numbers, Caddell told them, indicated a public appetite for a populist
challenger who could run as an outsider, exposing corruption and rapacity. He called it
the Candidate Smith project—the search for a political savior along the lines of “Mr. Smith Goes
to Washington.”
When Trump took an early lead in 2015, most of the political and financial world ignored him.
Jeffrey Sonnenfeld, a professor at the Yale School of Management, attended a salon that summer
at the Connecticut home of Larry Kudlow, the business commentator who now leads Trump’s
National Economic Council. “It was a lot of very deep-pocketed Republicans from Greenwich
and New York,” Sonnenfeld told me. “Not one person had a pleasant thing to say about Trump.”
Sonnenfeld urged them to take Trump’s chances seriously, but a fellow-guest, who worked for a
super PAC supporting Ted Cruz in the primaries, disagreed. “She said, ‘I’m a lifelong expert on
the psychographics of women’s voter behavior, and I can tell you that Donald Trump will never
get two per cent of Republican women voters,’ ” Sonnenfeld told me. “She got wild applause.
That was Kellyanne Conway.” (Conway, now a senior adviser to Trump, called this a “specious,
self-serving claim,” adding, “I don’t know ‘Professor’ So-and-So.”)
But Caddell and Hanley concluded that Trump was the closest thing they would find to a
Candidate Smith. He had none of Reagan’s optimism, but he had name recognition, money, and
a preternatural sense of how a billionaire could surf the rage kicked up by the financial crisis.
Their conviction persuaded Mercer to invest in Trump, and other wealthy donors followed. As
Election Day approached, Charlie Glazer, a Greenwich money manager who had served as
George W. Bush’s Ambassador to El Salvador, began talking to friends, “rationalizing why we
should all vote for Trump,” one recalls.
For some, it was a plainly calculated choice. Thomas Peterffy, a billionaire who owned the
largest es…
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