Stephanie Winston Wolkoff hadn’t yet gotten dressed when a doorman in her prewar Park Avenue apartment complex buzzed up to let her know someone was waiting for her downstairs. It was early Monday morning, the day before the presidential election, and she had a sneaking idea of who it would be. It wasn’t the first time she’d been roped into one of the numerous investigations into how money around Donald Trump’s inauguration—which Wolkoff, as Melania Trump’s ex-close friend and adviser, had helped plan—was spent. She threw on black jeans and a little suede jacket, pulled out a mask, and took the elevator down to meet the representative serving her a subpoena from the Trump Organization.
The 20-something-page document came from an attorney representing the president’s business, as part of a civil case out of the District of Columbia looking into inaugural spending. The Trump Organization is seeking documents related to inaugural spending, along with a recorded deposition at the end of the month as it relates to their defense. The subpoena follows revelations Wolkoff made in a best-selling book published in September, which detailed her concerns about how the Trump family planned, spent for, and oversaw the inauguration, as well as the unraveling of her long relationship with Melania. Along with the book, Wolkoff released audio recordings in which the first lady is heard downplaying the conditions in which migrant children separated from their parents were kept, as well as complaining about having to decorate the White House for Christmas.
That this is what the Trumps were focused on the day before the presidential race—where the fate of the country and their family hangs in the balance—jibes with the reality that the president was bracing for a life after the White House that could involve a legal nightmare. Wolkoff was not surprised; pettiness was always the point. If they want more from her, she said from her apartment, she has more to give. “They’re just not going to like it.”
So much of her life had been turned upside down by her association with Melania that it was a fitting cap. “I’m sort of numb,” she told me from her apartment. “I’m worried about what’s to come tonight, but I’m sort of optimistic. It’s not like last time.”
It’s hard to overstate how much of her world has changed since the previous election. Obviously, her friendship with Melania has disintegrated into a public sparring match. Wolkoff has portrayed the first lady as vapid, uncaring, and complicit in her husband’s administration. Melania has swiped back, calling Wolkoff “someone who clung to me after my husband won,” referring to her book as “idle gossip,” and her behavior as “dishonest.” In 2016, Wolkoff voted for Trump; this year, she not only cast an absentee ballot for Joe Biden, but she switched her party registration to Democrat. “When I voted four years ago, the only thing I was thinking about was my future with Melania,” she said. She spent that night at the Hilton waiting to celebrate. (She wore a bright-red pantsuit and texted Melania when she noticed the crowd getting restless. “People are starting to leave!” she wrote. “What are you doing?” Melania replied, “We’re on the way!”) Two days later, she went to the Trumps’ triplex on Fifth Avenue to congratulate her, and Melania asked her to come to D.C. “Of course,” she replied, though, as she wrote in her book, she now wishes she had declined.
This year, she was hunkered down at home. She made chicken soup for her son and iced cupcakes with her daughter. She posted videos to her Twitter feed urging her followers to vote for Biden. She’d seen footage of Melania casting her ballot in Palm Beach, mask-less in a Gucci dress. “I wanted to believe so badly,” she told me. “But she has done absolutely nothing but her hair and her makeup over the last four years. She took the easy way out and sabotaged everything. She really just did not care.”
There are plenty of Trump-era hallmarks, things that set it apart from any time period that’s come before. There’s the chaos, the cruelty, the punishing news cycle, the rallies and the tweets and the country more divided than ever. What’s always struck me, though, is the collateral damage Trump has left in his wake in such a short time. A number of the president’s closest associates, including Michael Flynn, Steve Bannon, Rick Gates, Paul Manafort, and Roger Stone, have ended up in criminal trouble. Many more, like Wolkoff, were either betrayed by the Trumps or have pulled a 180 themselves (often a combination of the two). All have had their lives irreparably changed by association. Trump is a wrecking ball, and those closest to him suffer the brunt of his destruction.
Michael Cohen is the classic example. His Trump association upended his life a million times in a million ways, with congressional investigations into Trump’s Russian ties, l’affair Stormy Daniels, the FBI raiding his office and home, his guilty plea and flip, his testimony, and the three-year prison sentence handed down to him by the Southern District of New York. All of it hangs in the air at his apartment, a block away from Wolkoff’s, though the mood was lighter than you’d maybe imagine on Election Day. He spent much of it watching the returns in his den. Like Wolkoff, he cast his vote for Biden. He’d woken up early, at 4 a.m., and walked to a polling place on 55th Street, where the people working recognized him and brought him through what he says was a seamless process. He got his coveted voting sticker and made his way back to his Trump-branded apartment building, where he is currently serving out the remainder of his prison sentence on home confinement.
Four years ago, Cohen was still with the Trump Organization. He was working for the campaign, talking to Trump day and night, paying off Stormy Daniels days before the election at Trump’s request to pave the path for his win. But Cohen saw one incident on election night as a sign that his former boss was pushing him aside as he ascended to real power. Cohen and his daughter Samantha made their way to Trump’s victory party, only to realize that they hadn’t been invited to the private party with the Trump family and true insiders. As he wrote in his book, Cohen was wise to the ways of Trump, and he knew he was being iced out.
This year, Cohen toggled between MSNBC and CNN in his apartment. His face was unshaven, and he had put on an oatmeal turtleneck when he woke up. “I love turtlenecks,” he told me. “It’s yummy. It’s cozy.” He made himself a turkey sandwich for lunch (he’s been cooking a lot during home confinement—lasagne, rigatoni bolognese, avocado toast with truffle oil) and settled in for the long haul. “I keep thinking that four years ago, I would have been standing to his right,” he said. Now, “I’m watching with popcorn in hand, getting ready for the proverbial shitshow.” He wouldn’t trade it, though he does wish he could see Trump’s face as results roll in. “I wish I was sitting with him in the residence as each state comes in blue so I could get a front-row picture of the grimace—that ‘I just sucked on the tartest lemon while someone farted in my face’ look. Within one minute of Trump losing, he’s going to television, to radio, to print, whining about how it was stolen from him, because he cannot accept loss; he cannot accept any blame and will never acknowledge that he lost because he’s arrogant and ignorant.”
Further uptown, Sam Nunberg didn’t totally disagree, he told me as he ate lunch at an Indian restaurant near his apartment. If the line at the polling place on his way home was short, he would pop in and cast a vote for Trump, his boss until 2015, when he was fired from the Trump campaign. If the line was too long, he’d skip it. “My vote doesn’t count in New York anyway.” Nunberg fell out with Trump and the two were involved in litigation, though he still supports some of the administration’s policies and stays close with some of its key higher-ups and hangers-on. Last election, he was doing TV hits for Sky News in Times Square before getting unhappily wasted at Dorian’s. He is now two and a half years sober. Every month, he celebrates by buying a new pair of sneakers. He chose a pair of Jordans for this first Tuesday in November.