We are in the final days of the first presidential contest between two New Yorkers in 72 years, since Thomas Dewey ran against Franklin D. Roosevelt: The 42-year-old Republican governor of New York used a Trump-style attack on the 62-year-old Democratic president, calling him “a tired old man.” On election night, the party and the wake will both be held in Manhattan. Hillary will hold hers at the Javits Convention Center, with its literal glass ceiling and, as The Times’s campaign reporter Maggie Haberman noted, an air of trolling: Back in the late 1970s, Trump wanted to build the center and slap the Trump name on it, but the city refused.
In this historically dreadful and mesmerizing election, which could lead to the death of the Republican Party and the ideological makeover of the Democratic Party, the New York aspect has been largely overshadowed. Only Lin-Manuel Miranda made a point of highlighting it, on “Saturday Night Live,” urging people to take their minds off the crazy election by coming to “Hamilton”: “It’s about two famous New York politicians locked in a dirty, ugly, mudslinging political campaign. Escapism!”
In the “single compact arena” of New York, E.B. White wrote, a gladiator and a promoter can come together in a city vibrating with great undertakings. “These two names, for the last two or three decades, represent what has been incredible and vulgar about this country at the same time,” says the Manhattan ad man and television personality Donny Deutsch. “We can trace our downfalls or upticks as a society through them.” The story of how Donald Trump and Hillary Clinton rose and reinvented themselves and embraced and brawled is the story of New York itself. It is a tale of power, influence, class, society and ambition that might have intrigued Edith Wharton, whose family once owned a grand home down the block from what is now Trump Tower.
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The Clintons started their move to New York from Washington in 2000, so Hillary could pursue her bid for the United States Senate and fly on her own after the Monica Lewinsky scandal. She had never lived in New York, but carpetbagging was no sin to cosmopolitan New Yorkers, who embraced Bobby Kennedy when he decamped from Massachusetts and suburban Washington in 1964, so she looked North to Daniel Patrick Moynihan’s Senate seat.
When they arrived, the Clintons found a lot of raw nerve endings among the moneyed elite, who were bitterly divided following Bush v. Gore. Although wealthy Democrats and Republicans in New York have largely united around Hillary this time, business executives were more suspicious of Gore than they were of the Clintons. In those days, Democrats were complaining that the election had been stolen from them, and Republicans were whinging that it had almost been stolen from them.
Hillary knew she should not be seen as a Manhattan insider, so just as Bobby chose Long Island as his base, she chose Westchester. She recast herself as a Yankees-loving New Yorker in the city and a Chicago-born daughter of the Great Lakes when she campaigned upstate. New York — and being a senator in the horrific aftermath of 9/11 — would change Hillary. “It toughened her up,” says Senator Charles Schumer of New York. “She’s harder-nosed about things. Life did that, but New York did, too.”
Bill also needed a reinvention. After the impeachment and the Marc Rich pardon, he was in bad odor. He had to abandon plans to rent lavish offices for their foundation in Carnegie Hall Tower for almost $800,000 a year after critics pounced. He moved instead into offices in Harlem for $210,000 a year. The mulligan-loving ex-president was snubbed by four of the prestigious Westchester County golf clubs he reportedly tried to join. As Trump marveled to me at the time: “Now Clinton can’t get into golf clubs in Westchester. A former president begging to get in a golf club. It’s unthinkable.” Bill started an elaborate campaign to improve his image, making speeches at colleges and enlisting former cabinet members and other surrogates to talk up his legacy. Once Bill moved up in public estimation, he moved downtown with the foundation.
With Hillary’s Senate bid underway, the Clintons held out their tin cup. They had been fund-raising in the city nonstop since 1990, but the asks intensified as they started their foundation in 2001 and rubbed shoulders with all the new wealth on Wall Street, which was driven by hedge funds and technology funds. With book deals and lucrative speeches and Bill’s role as an adviser to Ronald Burkle’s private-equity firm, Yucaipa, the Clintons worked their way out of the debt accrued by legal bills from a cascade of federal investigations to earn an estimated $230 million in the next 15 years.
As the Clintons fashioned a new life in New York, Trump was transforming himself as well — from a risk-taking developer facing bankruptcy to a low-risk licenser of his name for other people’s projects, from a brazen builder to a gilded reality-TV star on “The Apprentice.” He had come out of Queens, a pushy New York kid with family money but no social tools to climb the society ladder. “Even stuck out on Avenue Z, his head was always in Manhattan,” says Wayne Barrett, author of the biography “Trump: The Greatest Show on Earth.” Gwenda Blair, author of “The Trumps,” says Trump, resplendent in the ’70s in his three-piece burgundy suit with matching shoes and matching limo, recalled “this strapping lad from the provinces who comes to the city, like a figure out of Balzac’s ‘Lost Illusions.’ ”
The New York society scene was set by the Rockefellers and the Astors with a tradition of civility, philanthropy and the arts at its heart. Even those who make money the rough way — especially them — adopt this genteel facade. Michael Bloomberg is the quintessential emblem of this model and Donald Trump is the quintessential raspberry to it. One top New York foundation official who requested anonymity — many people will only speak anonymously about the Trumps and the Clintons, because both clans are known to be vindictive — notes that “in the community of plutocrats and superachievers who come to New York, Donald Trump is seen as persona non grata. He’s not a civic leader.” New York, this person says, is a place where private-equity C.E.O.s like Henry Kravis and Stephen Schwarzman see themselves making commitments to the public good. Their status doesn’t come only from being in charge of powerful corporations. “It also comes from some attachment to a hospital or university or cultural center. Trump was never part of that ecosystem.” When the tightfisted Trump hosts a charity event for veterans or a charity golf tournament, it is dismissed as something to polish the Trump brand. Trump has turned off many people in the worlds of real estate, banking and law with his strong-arming, fee-shaving or stiffing, bankruptcies and litigiousness. “Most real estate guys won’t go near him,” a leading New York financial executive says. “You lie down with dogs, you get up with fleas.”
Trump thumps his chest about money, acting as if he’s Bloomberg-wealthy, while the Clintons pretend they have less than they do. Trump wants to belong, to get more legitimacy by elbowing his way into the power crowd, while the Clintons passed that threshold of belonging after two terms in the White House. A top media mogul dismisses all three as outsiders: “No one here thinks of the Clintons as New Yorkers, and Donald is a bridge-and-tunnel person. He’s always been a poseur in New York.”
Trump realized that golf was his entree if he wanted to pal around with Bill Clinton, whom he considered a kindred spirit in some ways — a great man who attracted jealous haters. “Bill is kind of Trump with a dictionary,” one author who has written about New York real estate says. Trump had been obsequious in trying to lure Ronald and Nancy Reagan to his business empire, and tried just as hard with the Clintons. He happened to have his own country club with a golf course in Westchester, which he bought out of foreclosure in the late 1990s. He closed the club in 1999 to redevelop it from top to bottom and reopened it as Trump National Golf Club in 2002. It was six miles from the Clintons’ house, and Trump could play with him, ingratiating himself further by hanging photos of Bill on the wall. As of June, Bill still had a locker at Trump’s golf club.
Trump once told me that he rebuilt the club, in part, because he knew Bill Clinton would need a place to play. As Don Van Natta Jr., an ESPN senior writer, wrote in his book about presidents and golf, “First Off the Tee,” Trump enjoyed playing with the ex-president. “He’s got a lot of golf talent, but he really likes those mulligans,” Trump told Van Natta. “If he misses a shot, he wants to take another crack at it. It’s like life.”
Trump greased the wheels of his relationship with the ex-president and the senator, giving the Clinton Foundation a $100,000 gift from his own foundation. According to “Trump Revealed,” by Michael Kranish and Marc Fisher, Trump donated to Hillary’s Senate war chest six times between 2002 and 2009, for a total of $4,700, and between 1999 and 2012, he switched his registration among the Republican, Democratic and Independence parties seven times.
The friendship, on both sides, was a transaction. Not personal, as they say in the “The Godfather” — just business. Trump’s life in New York was all about promoting the brand and making money for the family business. It was the same for the Clintons. A former Clinton White House official puts it more bluntly: “This was a classic Clinton go-where-the-money-is move.”
“They all played the same game in the same town with the same thing in mind,” says Bernard Kerik, the former New York City police commissioner, who was invited to Trump’s third wedding and served prison time for tax fraud and other felony charges. “Better your relationships and build the business. It’s all about money and getting ahead and hedging your bets and playing the angles.”
Trump wasn’t on the dinner-party circuit. He lived in a narrow alternate universe called Trumpworld, and his favorite way to spend the evening was ordering a steak or cheeseburger (well done) from Fresco by Scotto, eating quickly and watching a sporting event on TV. “Trumpworld is a world he weaves for his own needs and desires, depending on what they are and when they are,” says Louise Sunshine, a former Trump Organization vice president, noting that Clintonworld is much broader and more global.
Though the Clintons might show up at some events and galas and friends’ birthday parties, they were never really around enough to become part of the society dinner-party circuit, either. When I asked Trump last summer to describe his relationship with the Clintons, he was neutral: “As a businessman, you have to get along with all politicians,” he said. “I wouldn’t say it was a close relationship.”
Hillary presents the trip to Trump’s wedding as a lark. “The dates worked,” a friend says. But some of her aides expressed surprise that she was going to such a gaudy affair; they believed Hillary rearranged her schedule because she thought Trump was a more important donor than he was.
‘They all played the same game in the same town with the same thing in mind.’
The senator and former president beamed in pictures, mingling with the starry crowd, which included Heidi Klum, Barbara Walters, Arnold Schwarzenegger, Sean Combs, Usher, Steve Wynn, Derek Jeter, Don King, Simon Cowell, Gayle King, Matt Lauer and Katie Couric, who got in trouble for her enterprising move of bringing a purse-cam. Paul Anka, Billy Joel, Elton John and Tony Bennett all performed.
André Leon Talley attended with Anna Wintour because the bride was going to be featured on the cover of Vogue, where he was then American editor at large. He had flown to Paris to shop with Melania for the dress — she chose a John Galliano for Dior strapless gown worth $230,000 and a Vera Wang cocktail dress to change into later — and he was “on duty” at the wedding and the reception paying attention to the “birthday cake of a dress” when Melania “was walking around or dancing.” He calls Melania “the most silky, well moisturized, meticulously groomed woman” he has ever known, adding that “dehydrated skin is so unattractive.”
Trump was a reality-show star now, starting his third hit season of “The Apprentice” on NBC. Just as his taste in his apartment at Trump Tower was “like Louis XIV dropped acid,” as Timothy O’Brien, author of “TrumpNation,” describes it, so was his third wedding straight-up Versailles. “This was a man building a ballroom for his trophy wife,” Talley said. “It was Baroque, the way he loves it. The marble was flown in from Italy, and the ceiling was like a palace, all gold, painted by artisans flown in from France. He had a full-on live symphony orchestra.”
David Patrick Columbia, the society editor, asserts that the Clintons were another accouterment: “Donald liked the fact that the Clintons were there because it was just another affirmation of who he had become in his life, a successful person. That’s what matters to him.”
Perhaps the collision of Donald Trump and the Clintons on the biggest stage of all was inevitable. But was it orchestrated? At the restaurant in Trump Tower last summer, I asked the mogul about the “Manchurian Candidate” buzz, about that phone call he got from Bill Clinton in May 2015, when the businessman and reality star was making up his mind whether to run. The Washington Post quoted four Trump allies and one Clinton associate as saying that Clinton encouraged Trump’s efforts to play a larger role in the Republican Party.
Roger Stone, author of “The Clintons’ War on Women” and a longtime confidant of Trump’s, claims that Bill urged Trump to get in the race and told him he thought he could get the nomination. “That’s why the people with the tinfoil hats are convinced the whole thing is a setup,” Stone says. “Bill can’t help himself from giving advice. He loves the game. He’s the great kibitzer.” Stone said Trump also asked Bill three years ago if anyone could be elected president as an independent, and Bill told him no.
I tried to get to the bottom of this murky story that day at Trump Tower, but when you’re dealing with Bill and Donald and truth, it’s an elusive goal.
“Did Bill tell you that you should run?” I asked.
“He didn’t say one way or the other,” Trump replied, over a plate of meatballs.
To make the whole conspiracy wackier, when I began fact-checking this story, the Trump Tower version flipped, with Trumpsters saying that the phone call entailed Bill trying to talk Donald out of running because the former president knew that Trump could beat Hillary.
This new version was met with eye-rolling and mockery from Clintonistas. “Bill Clinton is not Frank Underwood,” a former top aide says. “I guarantee you he did not call Trump with an uber-plan, where he was five moves down the chessboard. He has a theory: You’ve got to give a lot to get a lot. But he doesn’t meddle like that, telling people to get in and get out. Trump shouldn’t flatter himself that Bill gave a damn one way or the other. Trump was just another guy on the call list.”
No matter how Trump got into the race, the way he has conducted it has made Bill burn. Trump escalated his attacks after the Billy Bush hot mike incident, dragging Bill’s accusers back onto the stage. No one else would have gone there or said, as Trump did, that Hillary had “one of the great women-abusers of all time sitting in her house, waiting for her to come home for dinner.” As a Clinton ally ruefully notes, “The last 15 years, everyone had forgotten about that, and now it’s back.” Trump also eagerly pounced to lash the Clintons to an astonishing new twist in the F.B.I. email investigation, involving Anthony Weiner, the estranged husband of Hillary’s closest aide, Huma Abedin, and his sexts to a 15-year-old North Carolina girl.
New York elites have gone from flabbergasted that Trump got this far to debating how the Trump family and one of Trump’s top strategists, Jared Kushner, Ivanka’s husband and the publisher of The New York Observer, will be received if they have to slink back into town. Some people say the attitude toward the Trump children will be more lenient; others think that the Trump brand is irrevocably damaged and that the whole family will be pariahs.
“Will the word ‘Trump’ be used almost in profanity for some time to come among average New Yorkers?” asks Hank Sheinkopf, a veteran Democratic political consultant. “Likely so.”
It may be beginning to dawn on Trump that he has thrown acid on his brand. He left the campaign trail during the final push to promote his new Washington hotel. The hotel is clearly struggling, cutting its expensive room rates and losing the famed chef José Andrés after Andrés decided Trump was “a racist, a divider.” I went to check it out recently, and it had a deserted feel. There was one African-American family posing under the Trump sign — giving a thumbs-down — and a strip of yellow crime tape across the front after vandals wrote “Black Lives Matter” on it.
“I can tell you, in my crowd, they would rather not do anything associated with Trump,” says one advertising and marketing big shot. “People are nauseated by what he’s doing.”
Cindy Adams, the New York Post columnist, disagrees: “He’ll go back to being the most famous face on this planet. No, his brand won’t be hurt. Trump will be Trump. Everybody will still want to meet him.”
Trump has said he hopes that Chelsea and Ivanka — who shared the problems of coming of age when their fathers were enmeshed in very public affairs — can remain friends. But on the Clinton side, people privately play down the friendship, saying that Ivanka, as with her father and the Clintons, was the one pushing the alliance. “There’s no Ivanka-Chelsea relationship,” the foundation executive says. “There was an Ivanka P.R. moment. It was a transaction. They both got what they wanted.”
Some say it will be hardest for Kushner, an Orthodox Jew who got in deep with helping Trump as anti-Semitic sentiment swirled around the candidate. Joe Conason, author of “Man of the World” and a former employee of Kushner’s at The Observer, says: “People will remember this. Maybe you could get away with this in parts of Florida. But in New York City, this doesn’t fly.”
One friend of Trump’s from the real estate world is worried that Trump does not understand how the groups he has derogated and demeaned will wreak revenge on him. “He’s alienated women,” the friend says. “He’s alienated wealthy people. He’s alienated people from the Middle East. He’s alienated people from Latin America. These are all fertile ground where people could buy condos from him.”
At the annual Al Smith dinner last month at the Waldorf Astoria, a white-tie charity fête put on by the Catholic Archdiocese of New York that brings together high society and media and features humorous speeches by politicians, Trump was greeted warmly enough after he was introduced by Al Smith IV. “A kid from Queens with a big heart and a big mouth is without question a New York institution,” Smith said.
But when Trump began to make harsher cracks about Hillary toward the end, out of sync with the tone of the event, he was repeatedly booed — spurned by the same Manhattan elites whose approval he had spent so long seeking. Afterward, he fled quickly with Melania without talking to anyone. As Trump returned to the seclusion of his Fifth Avenue Xanadu, he was playing a scene of megalomania and mortification straight out of one of his favorite movies, “Citizen Kane,” about the fall of a brash New York mogul who flew high, gave politics a shot and then had a steep fall after a sex imbroglio. “ ‘Citizen Kane’ was really about the accumulation,” Trump once said. “At the end of accumulation, you see what happens, and it is not necessarily all positive.” Hillary, meanwhile, was spotted nearly 20 minutes after he left, still laughing and mingling with the crowd.
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