As Hillary took her seat in the Senate in 2001, Trump joined the Democratic Party. Years later, he explained the decision: “I said to myself, if I ever ran for anything in New York, which I thought about, you virtually can’t get elected as a Republican.” Trump gave his first big endorsement after joining the Democratic Party to one of the most liberal candidates running for mayor of New York City. Fernando Ferrer had been the Bronx borough president and was trying to become the city’s first Hispanic mayor, positioning himself as a liberal counterforce to outgoing Republican mayor Rudolph Giuliani. Ferrer thought Giuliani’s focus on policing and the commercialization of Times Square had come at the expense of the city’s lower and middle classes, what he called the “other New York.” He campaigned with the Reverend Al Sharpton, rallying black and Latino voters. He supported the right to late-term abortions.
On the eve of the runoff, Ferrer held a press conference with Trump, hoping the last-minute endorsement would swing the election his way. In the weeks after the September 11 attacks, which brought down the twin towers of the World Trade Center, Ferrer had endorsed a plan to rebuild the lost office space in the outer boroughs. Trump told reporters the plan was “very smart.”
Ferrer was surprised to win Trump’s support, wondering to himself, “What am I doing here?” This was not what he considered “serious politics.” But if it helped him win office, he would take it. Ferrer lost the primary to Mark Green, whom Trump then supported by giving his campaign $4,500. Trump’s belief that only a Democrat could win in New York City turned out to be misguided. Michael Bloomberg, a billionaire media mogul, ran as a Republican and won the general election.
Trump continued to help politicians from both parties, notably including a dynamic former prosecutor and Democrat, Eliot Spitzer. Trump had encountered Spitzer in the nineties, when he was vying to become New York’s attorney general under the slogan Total Change. “You’re a nice kid, but you’re never going to win,” Trump told him. In 1998, Spitzer won, and Trump sent him a handwritten letter. “I told you that you wouldn’t win. You did. Good luck,” it said, according to Spitzer. Inside the envelope was a $10,000 check for Spitzer’s reelection. Trump would later pledge to help Spitzer raise $250,000 for his successful gubernatorial campaign, including hosting a cocktail party at his Trump Plaza apartment. Spitzer resigned in a prostitution scandal in 2008. In 2013, Trump slammed Spitzer, calling him a “horrible” governor and attorney general “who ruined many good people.”
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TO TRUMP, POLITICAL DONATIONS were a cost of doing business, suggesting that his practice of politics was transactional, not ideological. “I give to everybody. When they call, I give,” Trump said. “And you know what? When I need something from them—two years later, three years later—I call them. They are there for me.” Frank Sanzillo, Trump’s lobbyist in New York in the late 1990s and early 2000s, said Trump was privately dismissive of politicians: “He laughed about them, like, ‘Let’s give his campaign twenty-five thousand dollars, that’ll shut him up.’ And it was our job to translate that to the politician as ‘He loves you.’ ” Trump also was loath to attend political fund-raisers, often asking Sanzillo, “How much more do I have to give not to show up?”
Trump and his major companies gave at least $3.1 million to local, state, and federal candidates from both parties between 1995 and 2016, not including donations that may have flowed through limited liability corporations that Trump controlled. He donated $620,000 to the Republican Governors Association between 2009 and 2014. From 1995 to 2006, he also gave $11,500 to Charles Rangel, the Democratic congressman from New York (“The only thing Donald Trump ever talked to me about was Donald Trump!” Rangel recalled). But Trump said his votes for president were consistently Republican. He voted for Bush in 2000 and said he lost respect for the forty-third president because of his handling of the war in Iraq, which he would later call a “disaster.” Trump maintained that he had been against the war from the beginning, but when radio host Howard Stern asked Trump on September 11, 2002, if he supported going to war—six months before the invasion—he responded, “Yeah, I guess so. You know, I wish the first time it was done correctly.” (Five days after the invasion began, a Washington Post reporter overheard Trump at an Oscars after-party calling the war a “mess.”) Still, he voted for Bush again in 2004 because he felt it was important to “carry the Republican line.” Recalling the 2004 vote, Trump said he showed his distance from Bush by not throwing fund-raisers for him. He gave the campaign $2,000, according to federal filings.
Trump’s public statements sent mixed signals about his political leanings. In 2006, he said that Senator John McCain, who would become the 2008 Republican nominee, could not win because he advocated sending more troops to Iraq. Trump praised the eventual Democratic nominee, Senator Barack Obama of Illinois, for his “wonderful qualities.” Nonetheless, Trump contributed $3,600 to McCain during the 2008 campaign and voted for him.
Trump changed parties seven times between 1999 and 2012. After registering as a Democrat in 2001, he switched back to the Republicans in 2003. He became a Democrat again in 2005 and a Republican in 2009. He chose not to be affiliated with any party in 2011. Then he returned to the GOP in 2012, once again stoking speculation that he would seek the presidency. Asked what he would say to critics who saw the constant party-switching as proof that he had no core beliefs, Trump responded, “I think it had to do more with practicality, because if you’re going to run for office, you would have had to make friends.”
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TRUMP’S CELEBRITY STATUS PROMPTLY put him among the 2012 front-runners. An NBC–Wall Street Journal survey among Republican primary voters released in early April 2011 showed him tied for second behind front-runner Mitt Romney. Among Tea Party supporters, Trump led the field. He had bashed Obama with an intensity he had never displayed for Obama’s predecessors. He called the president’s signature health care law a “job killer!” and “one of the greatest threats our country faces.” He drew wide attention for focusing on the long-discredited assertion (though one accepted by at least a fifth of the population) that the president had not been born in Hawaii, but in Kenya, his father’s native country. On NBC, Trump expressed “real doubts” about whether Obama was US born, cementing his role as a leader in what became known as the birther movement. Provocatively, he suggested that he had private investigators combing through records in Hawaii: “I have people that actually have been studying it, and they cannot believe what they’re finding. . . . I would like to have him show his birth certificate.”
Obama had long ignored such taunts. But three weeks later, as Trump prepared to arrive in New Hampshire for an exploratory visit, Obama announced that he had sent a member of the White House counsel’s office to Hawaii to bring back a copy of his long-form birth certificate. Obama put the document on public display, explaining, “We do not have time for this silliness.” Days later, when Trump was a guest of the Washington Post at the annual black-tie White House Correspondents Dinner, Obama ridiculed the real estate mogul: “Now, I know that he’s taken some flak lately, but no one is happier, no one is prouder, to put this birth certificate matter to rest than The Donald. And that’s because he can finally get back to focusing on the issues that matter—like, did we fake the moon landing?” The audience roared with laughter while Trump looked stone-faced, although he later insisted the jokes were fine and the evening “phenomenal.”
Two weeks after the dinner, Trump announced he would not run in 2012, saying, “Business is my greatest passion and I am not ready to leave the private sector.” In a later interview, he explained the decision: “My children were younger. I was doing numerous jobs, many jobs, and I really wanted to wrap them up. . . . I had a signed contract with The Apprentice.” On February 2, 2012, he endorsed Mitt Romney: “We really have the opportunity to do something great for our country.” Trump became an outspoken surrogate for Romney, recording calls that were automatically sent to voters du
ring the primaries, attacking Obama on Twitter, and offering to give $5 million to a charity of Obama’s choosing if he released his college transcripts and passport information. Obama ignored the request. On Election Day, Trump went to Boston to attend what was supposed to be a Romney victory party and told the Boston Herald he “felt good” about how things would turn out. After the results came in, he was livid at the loss, and he took to his increasingly favored medium, Twitter, to vent his frustration: “This election is a total sham and a travesty.” “Let’s fight like hell and stop this great and disgusting injustice!” “We can’t let this happen. The world is laughing at us.” “We should march on Washington and stop this travesty. Our nation is totally divided!” Trump said years later that if Romney had relied on Trump more, he might have won the election. “But they chose not to use my services—which was fine with me because I’m very busy, you know,” Trump said.
Twelve days after the 2012 election, Trump filed an application with the US Patent and Trademark Office for a phrase he wanted to be his own: Make America Great Again.
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The Worth of a Man
I’m really rich.” With those words, Donald Trump pointed to what he considered a central qualification for his run for the White House. At Trump’s campaign announcement address on June 16, 2015, his aides passed around a document stating that he was worth more than $8.7 billion in 2014—a fortune that would rank him among America’s wealthiest people. Trump was hardly the first person of great wealth to aspire to the presidency. President George Washington had overseen a vast plantation made possible by slavery. Mitt Romney, the failed 2012 Republican nominee, became wealthy running Bain Capital, a private equity firm. Few, if any, however, had trumpeted quite so loudly as Trump the notion that building a profitable business was a central qualification. Washington was a general who led the nation to independence; Romney was a Massachusetts governor who won passage of a health care program. Trump had never held public office, and he relied to an extraordinary degree on his carefully crafted image as an astonishingly successful executive. Trump argued, in essence, that his wealth made him uniquely qualified to be president, that he would make America as successful as he was. “I’m proud of my net worth,” Trump said. “I’ve done an amazing job.”
But the document highlighted an issue that had trailed Trump from his earliest days as an entrepreneur, real estate developer, and showman: there was no way to verify the bottom line. One month later, his campaign issued another statement that said Trump’s “net worth is in excess of TEN BILLION DOLLARS.” When Trump’s campaign submitted its federally mandated financial disclosure statements to the government, it boasted that the forms were “not designed for a man of Trump’s massive wealth.” For decades, Trump had made his net worth a major component of his identity as a master dealmaker. He had publicly slammed or sued some of those who questioned his self-valuation. Trump didn’t calculate his worth in dollars alone; he also put a value on the perception that he was extraordinarily wealthy. If Trump had his way, no one would question his claims to great wealth. Yet his claims were questioned, time and again.
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THE QUESTIONS BEGAN DECADES earlier as Trump emerged as a public figure. In 1976, a New York Times profile quoted him saying he was worth more than $200 million. Although net worth and income are different, some skeptics argued that the big number seemed to be at odds with a New Jersey Casino Control Commission report, which showed that he claimed his taxable income in 1976 was $24,594. Trump also received a $6,000 gift from his parents every December, and an escalating series of payouts from family trusts. Questions increased when it turned out that Trump had paid no income tax in 1978 and 1979. Using tax deductions including real estate depreciation, he claimed a negative income of $3.8 million during those two years. The same report showed that he had borrowed $7.5 million from his father, had used his take from the already-indebted Grand Hyatt to back his Atlantic City debt, and had relied on a $35 million line of credit from Chase Manhattan.
By the early 1980s, after Trump had begun construction of Trump Tower, he dramatically increased his estimate of his net worth. He learned that Forbes in 1982 was preparing to launch an annual ranking of America’s four hundred richest people, known as the Forbes 400. Money, Trump said later, was a way to “keep score” in life. The list was hardly scientific, and staffers had limited time to produce it. They faced a conundrum: How could they estimate Trump’s net worth when he ran a private company and offered limited financial documentation? “You couldn’t get at Trump’s cash flow,” said Harold Seneker, then a Forbes senior editor in charge of the rich list. That made it especially difficult to pin down the value of his holdings. Editors guessed at what a property might sell for, then subtracted the publicly known debt related to it. Trump told the magazine he was worth about $500 million.
Because of the uncertainty, Forbes’s editors decided to offer a combined estimate for Fred and Donald Trump at the time, $200 million. “Our rule of thumb was to divide whatever [Trump] said by three,” Seneker said. The Forbes list continued to boost Trump’s value each year. In 1984, the magazine estimated he was worth $400 million. Then it was $1 billion in 1988. “I’m breaking every record in the history of Atlantic City,” Trump said later. Trump carried a lot of debt, but he boasted in 1988 that he was protected from danger: “None of the debt is personally guaranteed. If the world goes to hell in a handbasket, I won’t lose a dollar.” Behind the scenes, though, Trump was putting his finances in peril as the result of a borrowing-and-spending spree he went on shortly before a collapse in real estate values.
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ON NOVEMBER 10, 1988, Trump stepped onto the Late Night with David Letterman stage in New York and took his seat next to the TV host. Letterman introduced Trump as a person who knew “everything there is to know about money, finance, economy, budgets, so on and so forth.”
“You’re worth, like, four billion dollars or something, right?” Letterman asked.
“I hope so,” Trump said with a restrained smile.
“Is there any way a guy like you could go broke?” Letterman said, drawing a wave of laughter. “I’m serious. Could you weather any financial storm and come out still a tycoon?”
Trump turned serious. “I would like to think I could weather most. It’s a great time to really save as much money in dollars as you can.” Trump himself wasn’t saving. He had just bought the Plaza Hotel across from Central Park and was launching the Trump Shuttle. Few knew it, but the level of debt behind his empire was soaring. One man who had suspicions about Trump’s viability was a little-known real estate specialist named Abe Wallach.
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IN 1989, WALLACH, A senior vice president at a New York real estate firm, appeared on the public television show MacNeil/Lehrer NewsHour to speak about Trump’s finances. The segment, titled “Trumpty-Dumpty,” asked whether the mogul could “keep his financial empire afloat.” The situation sounded ominous. Trump faced a $2 billion debt and needed a $60 million loan to keep his business going. “Trump, the cash crunch,” a reporter intoned. “Could it really be happening to the symbol of business success in the roaring eighties?” The report transitioned from a scene of a suave-looking Trump to newspaper headlines such as “Banks Squeeze Trump.”
After a rundown of Trump’s financial woes—highlighted by the contradiction between Trump’s prescriptions in Trump: The Art of the Deal and his corporate bankruptcies—the program introduced Wallach. Grave and thoughtful-looking, the bespectacled Wallach said Trump could blame some of his troubles on the declining real estate market. But that didn’t explain everything. Trump took on too much debt, Wallach said: “The reality is, if you pay too much for properties, and if your ego is as large as his was—is—and you just buy everything in sight, part of the blame has to squarely rest in your own lap.”
Trump was incensed. A week after the show, a visitor to Wallach’s New York City loft handed him a thi
ck bundle of documents. On a cover sheet were the words TRUMP vs. WALLACH. Wallach said the document informed him and his company that they were each being sued for $250 million in damages, alleging slander and defamation of character. Wallach was stunned as he faced the possibility of ruin. (Years later, Trump said he did not recall suing Wallach.) Trump’s attorney said he would withdraw the lawsuit if Wallach agreed not to criticize Trump on TV, according to Wallach’s account.
Soon afterward, Trump himself called Wallach. “Abe, I hear you are a very smart guy. You don’t want to knock me. After all, I am the major real estate force in New York, and knocking me is knocking New York,” Trump said, according to Wallach. Trump suggested he wanted to hire Wallach and invited him to Trump Tower. Weeks later, Wallach arrived and described for Trump a Hudson River waterfront project in New Jersey, featuring thousands of housing units, millions of square feet of office space, and a major mall. Trump, who was intrigued by the waterfront project and impressed by Wallach, eventually offered him a job as a real estate executive for a salary of $175,000; Wallach accepted the offer.
As Wallach settled into the job, Trump’s empire was increasingly under siege from bankers and bondholders. Trump maintained that everything was fine. Around this time, he submitted documents to the Casino Control Commission showing assets of about $3.6 billion, including “Real Estate Properties Owned Directly,” personal residences, and “Commercial Airlines.” Commission officials who factored in Trump’s debts calculated his net worth at $206 million. The editors at Forbes seized on the commission’s report and published a May 1990 story detailing Trump’s severe cash-flow problems, “unrealistically optimistic” real estate assessments, and billions in debts. The story concluded, “Trump badly needs an additional source of coin.” Forbes estimated Trump’s net worth at $500 million, down from $1.7 billion the previous year. That knocked Trump off the Forbes rich list; he would be absent from it for six consecutive years. Now Trump attacked the list, whose ranking he had previously coveted. It was, he said, a “very inaccurate survey” and “a sloppy, highly arbitrary estimate of certain people’s net worth.”
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