After Yanukovych fled Ukraine, Manafort struggled to find new clients. He managed to secure a $6 million contract to represent a slate of former Party of Regions candidates, but in the end, he received only a fraction of the promised payment. By 2015, Manafort’s cash-flow bonanza in eastern Europe had completely evaporated, touching off an acute financial crunch. Manafort’s lavish lifestyle had come with staggering monthly bills—in certain years, he paid more than $200,000 for landscaping on the Hamptons estate alone—and it didn’t take long for debts to mount. There were other sources of fiscal pressure too. Lawyers representing Oleg Vladimirovich Deripaska, the billionaire Russian oligarch who first sent Manafort to Kiev, were after him about the missing $19 million that Manafort had invested on his behalf in a Ukrainian telecommunications company in 2007. Deripaska later asked for the return of his investment funds, as the global financial crisis was wrecking his balance sheet. When Manafort failed to repay him, Deripaska filed a lawsuit in 2018. A Manafort spokesman told the Washington Post that “we are surprised by the filing,” adding that he believed that the issue had been “addressed and resolved years ago.” The case has been on hold since the federal government placed sanctions on Russia’s government and industry, including Deripaska’s company.
As the squeeze on Manafort’s bank account intensified, the man whose annual clothing budget regularly exceeded $210,000 began scrambling to save cash. “He is suddenly extremely cheap,” his daughter Andrea remarked in a 2015 text message, which was contained in the years’ worth of her texts that were obtained by hackers and posted online. While making plans for a prewedding reception for Andrea and her fiancé, Manafort had refused to pay for drink mixers or ice, recommending instead a cut-rate event with paper plates and hot dogs. “Hot dogs. Can we just discuss how gross that is,” Manafort’s other daughter, Jessica, wrote in a text exchange with her sister, Andrea. “This isn’t a fucking grill out,” Andrea replied.
As these financial troubles escalated, Manafort faced a crisis on the home front. A few months after his break with Yanukovych, his daughters discovered that he was carrying on an elaborate affair. Manafort had set up his paramour, who was more than three decades younger than he, with a Manhattan apartment, a Hamptons beach house, and access to an American Express card. “He was fucking his mistress when Grandma was in surgery,” Andrea wrote in a text. In the spring of 2015 Manafort’s wife, Kathy, confronted him about the affair. He broke down, begged forgiveness, and checked into an Arizona addiction clinic, according to a text from one of Manafort’s daughters. While at the clinic, Manafort’s only contact with the outside world came during the fifteen minutes of phone time he was allotted per day. “I guess he sobs. Like a lot,” Andrea texted a friend. Over time, his daughters grew concerned he might harm himself. “He is acting like he is going to end his life,” Jessica texted Andrea. “He is writing a letter to mom and then he said he will be gone forever,” Andrea replied.
While Manafort was coming unglued at the Arizona treatment center, a celebrity client of his former lobbying firm was gliding down an escalator at Trump Tower on his way to the press conference where he would announce his White House bid. It was Manafort’s dream to get back into American politics, Gates says. But such a return had always seemed impossible. In the two decades since he last worked on a US presidential campaign—Bob Dole’s ill-fated 1996 venture—Manafort’s ties to flashy arms dealers and vicious foreign tyrants had made him too much of a liability for any mainstream candidate. During the 2008 presidential race, according to Gates, one of Manafort’s well-connected friends had urged the top brass of John McCain’s campaign to bring him aboard, but to no avail. Trump was different. As an outcast of the Republican establishment, he didn’t have many experienced Washington operatives in his orbit. And thanks in part to all the scandal and bad press in his own past, he was more willing to overlook a few problems on the resumes of the people he hired.
Manafort shared some loose affiliations with Trump. In addition to his ex-firm’s lobbying work on behalf of the New York mogul in the 1980s and 1990s, Manafort and his wife had squired Trump around the 1996 Republican National Convention, in San Diego. At one point, as Kathy led Trump through the pomp and excitement of the convention floor, she heard Trump speaking to himself.
“This is what I want,” he said. “This is what I want.”
In the years after Manafort purchased his Trump Tower apartment, he would occasionally exchange friendly small talk with the real estate billionaire when they bumped into each other in the building. There were also some mutual friends. Manafort’s old lobbying partner Roger Stone had been a political advisor to Trump when his casino business was a lobbying client of Black Manafort. The billionaire private equity founder Tom Barrack had been close with both men for many years.
By early 2016, Manafort was taking the first steps of his improbable comeback. With his finances in shambles, his personal life in chaos, and his emotional state so despondent that he was hinting at suicide, he would use the New York playboy-turned-right-wing-firebrand as his vehicle out of the darkness. After his four weeks in rehab, Manafort reached out to his buddy Tom Barrack. “I really need to get to” Trump, he said, according to what Barrack told the Washington Post.
Manafort set himself to securing a role in the famously antiestablishment campaign. With Barrack acting as an intermediary, he delivered a five-page pitch to Trump in February 2016 in which he recast his exile from Republican politics as a selling point. “I have had no client relationships dealing with Washington since around 2005. I have avoided the political establishment in Washington since 2005,” Manafort wrote. “I will not bring Washington baggage.” To accentuate this message, Manafort referred to Karl Rove, the ex–George W. Bush strategist who’d emerged as a vocal Trump critic, as “my blood enemy in politics” stretching back to the College Republicans in the 1960s. Manafort also alluded to lobbying work he’d done for Trump in the past, and he mentioned his place in Trump Tower.