Trump remained outside the political system, but he continued to influence it through his lobbyists and campaign contributions. Trump spent millions to sway politicians and bureaucrats, especially to guard his Atlantic City casinos from encroaching competitors. And he wasn’t shy about employing his signature bravado on Capitol Hill.
In 1993, while testifying before a congressional committee, Trump questioned whether members of a Connecticut tribe operating the Foxwoods casino, which he viewed as serious competition to his Atlantic City operations, were really Native Americans. “They don’t look like Indians to me,” Trump told the House Native American Affairs Subcommittee. He said the tribe would not be able to keep organized crime out and he predicted “the biggest scandal ever.”
The comments echoed a racially charged interview Trump had given months earlier. “I think I might have more Indian blood than a lot of the so-called Indians that are trying to open up the reservations,” Trump had said on shock jock Don Imus’s show. Imus referred to tribes hoping to open casinos as “drunken Injuns,” comparing them to an African-American basketball star: “A couple of these Indians up in Connecticut look like Michael Jordan, frankly.” Trump replied: “I think if you’ve ever been up there, you would truly say that these are not Indians.” Representative George Miller, a California Democrat who chaired the congressional hearing, took aim at Trump’s comments to Imus and on Capitol Hill: “Mr. Trump, do you know in the history of this country where we have heard this discussion before? ‘They don’t look Jewish to me,’ ‘They don’t look Indian to me,’ ‘They don’t look Italian to me.’ And that was the test for whether people could go into business or not go into business, whether they could get a bank loan: ‘You are too black; you are not black enough.’ ” Trump responded that casinos on Indian reservations got unfair, “discriminatory” advantages.
In 2000, when New York was considering expanding Native American casinos in the Catskill Mountains, Trump played a role in a series of explosive TV, newspaper, and radio ads that accused members of the Mohawk Indian tribe of having long criminal records and ties to the mob. The ads showed pictures of cocaine lines and syringes and asked, “Are these the new neighbors we want?” The campaign against Indian casinos included an ostensible telephone survey in which respondents who opposed gambling in New York were transferred to Governor George Pataki’s office to register their complaints. A group called the Institute for Law and Safety sponsored the ads; the group was funded by Trump and facilitated by his longtime lobbyist, Roger Stone. Stone, a Republican operative and fixer, had worked on Richard Nixon’s Committee to Re-elect the President in 1972, taking part in campaign high jinks that emerged during the Watergate scandal. Stone’s role in the affair was minor but colorful: he donated money to Pete McCloskey, Nixon’s rival in the 1972 Republican primary, under a fake name—the Young Socialist Alliance—then tipped off a newspaper about the rival candidate’s supposed communist supporters. Stone first met Trump while on the hunt for political donations on behalf of Reagan’s campaign in 1980. Stone visited Roy Cohn, Trump’s attorney at the time, and Cohn steered Stone to Fred and Donald Trump. Stone developed a fondness for the younger Trump and would eventually fill the void left by Cohn’s death. Stone teamed up with Paul Manafort (later Trump’s 2016 presidential campaign manager) and others to start a lobbying firm in 1981, after Reagan’s election. Trump became one of the firm’s first clients.
Nearly two decades later, Stone was at the center of Trump’s under-the-radar antigambling campaign in New York. Trump had paid more than $150,000 for the ads—on top of more than $300,000 he reported spending to lobby New York legislators over the first half of 2000. But Trump and Stone never reported the ad spending as a lobbying effort, as state law required. They admitted their role only after regulators launched an investigation. The state lobbying commission imposed its largest-ever civil penalty—a $250,000 fine—and Trump agreed to issue a public apology. “It’s been settled,” Trump told reporters. “We’re happy it all worked out nicely.” As part of the settlement, the lobbying commission agreed not to refer the case for criminal prosecution. A violation of the state’s lobbying act carried the potential for a misdemeanor charge.
Even then, Trump continued to fight the proposed casino in the Catskills, casting upstate gaming as a threat to New York City. “It will destroy the progress that’s been made in New York City,” Trump said on the day he agreed to the fine. “It will drain money out of the city. Instead of buying cars and apartments, they’ll be spending money at casinos.” That, of course, was what his business relied on in Atlantic City, but Trump apparently saw no contradiction in fighting against gambling in New York if it helped his interests in New Jersey.
Even as he warned of the dangers of Indian gambling in New York, he pushed for an Indian casino in Connecticut. Trump had a stake in that project, partnering with the Paucatuck Indians. Under a 1997 pact, Trump had agreed to pay for efforts in Washington to get the tribe the federal recognition it needed to operate a casino. He also agreed to provide his expertise. In exchange, the tribe agreed to give Trump a management fee based on a percentage of the future casino’s revenues. Trump hired lobbyists at the Miami-based firm Greenberg Traurig to help get the tribe federally recognized. Lobbyist Ronald Platt represented Trump Hotel & Casino Resorts Inc. in 1999 and 2000. The tribe won federal recognition in 2002, but backed out of the deal with Trump shortly afterward. There would be no casino for Trump in Connecticut, but he still owed the lobbying firm more than $600,000.
Trump had been slow in paying, so Platt visited him in Manhattan. The lobbyist got a taste of what happened when Trump didn’t win. “I’m here to get us paid,” Platt told Trump.
“It should be so prestigious to represent me that you should do it for free,” Trump responded, according to Platt.
“Bullshit,” Platt answered. Trump then picked up a yellow legal pad, slammed it onto a table, and stormed out of the room, according to Platt. An intermediary chased after Trump and came back with the check fifteen minutes later. Platt left the office and deposited the check as soon as he could—before Trump could change his mind. Trump said later that he didn’t remember Platt, but added, “If I held back payment, it was probably because he did a lousy job.”
• • •
WHILE TRUMP REBUILT HIS empire and his personal life, an epic battle was under way for the presidency. In 1992, a new face on the political scene, Governor Bill Clinton of Arkansas, defeated President Bush and a billionaire independent, Ross Perot. Clinton became the nation’s forty-second president in January 1993 and promptly announced that his wife, Hillary Rodham Clinton, would play a major role in his administration, in charge of creating a national health care plan. Three months later, Tony August, the organizer of a gaming industry awards ceremony in Atlantic City, wrote to the White House and invited President Clinton to the event. The invitation was a long shot, but the organizer thought Clinton would hit it off with the guest of honor: Donald Trump. “I’m not a matchmaker,” the organizer wrote, “but if you two don’t know each other, you should. You have much in common—age, broad vision for the future, and most importantly, the resources and desire to make America bigger and better than it already is.” The Clintons didn’t make it to the event with Trump, but their social and professional circles began to intersect. Trump, for example, was one of about fifty prominent officials and political fund-raisers President Clinton sat down with during a trip to Manhattan in 1994.
There were limits to the social niceties. In 1996, Clinton’s personal secretary floated the idea of sending a letter to Trump on his fiftieth birthday. Three days later, the same secretary sent instructions to the person who handled Clinton’s personal correspondence: “Cancel the letter to Donald Trump.” Trump, though, was a vocal Clinton supporter in the late 1990s. “I think Bill Clinton is terrific,” Trump said on December 27, 1997, on CNN’s political talk show Evans & Novak. “I think he’s done an amazing job. I think he’s probably got th
e toughest skin I’ve ever seen, and I think he’s a terrific guy.”
One month later, reports surfaced that Clinton had had a secret sexual relationship with an intern named Monica Lewinsky, beginning when she was twenty-two years old in 1995 and lasting for more than two years. Trump was unperturbed, becoming one of Clinton’s most vocal backers. “The best thing he has going is the fact that the economy’s doing great,” Trump said in August 1998, days after Clinton finally admitted a relationship with Lewinsky. “I’ve never seen anything like it. You know, they talked about the eighties were good. The nineties are better.” When a former Arkansas state employee, Paula Jones, sued Clinton, alleging sexual harassment, Trump called her “a loser.” Trump suggested that if he were a candidate, he would face similar controversy: “Can you imagine how controversial that’d be? You think about him with women. How about me with the women?”
Clinton was impeached by the House for lying to a grand jury about the Lewinsky relationship, but the Senate did not convict him, enabling him to complete his second term. Trump, meanwhile, began thinking more seriously about succeeding him. As a new election approached, Stone, Trump’s longtime lobbyist, examined the potential field, led by Republican George W. Bush and Democrat Al Gore. Stone said this could be Trump’s moment, and that the path forward might be within a third party. The country seemed receptive to candidates from outside the two major political parties. Ross Perot, a Texas billionaire with no political experience, had won 18 percent of the vote in 1992 and was still popular. Trump was particularly familiar with the rise of Jesse Ventura, a professional wrestler Trump knew from WrestleMania who had improbably won the governorship of Minnesota in 1998 on the Reform Party ticket. Ventura had made his name parading in a feather boa and, as a World Wrestling Federation commentator, mocking Hulk Hogan. If Ventura could go from being known as The Body to The Governing Body, maybe Trump could become president.
• • •
MORE THAN THREE MONTHS after his father’s funeral, on October 8, 1999, Trump announced on Larry King Live that he was leaving the Republican Party to join the Reform Party, which was eligible for federal funds because of Perot’s performance in the previous two presidential elections. Fed up with the two-party system, Trump announced that he was forming an exploratory committee to run for president. In little more than a year, Trump’s assessment of the Clinton years had made a U-turn. “I think there’s a great lack of spirit in this country,” Trump told King. “You know, what happened over the last four years is disgusting, and I just think there’s a tremendous lack of spirit, and I think the spirit has to be brought back.”
Despite joining the Reform Party, Trump said his role model was Reagan, notwithstanding his criticism twelve years earlier of the former president. Trump still wasn’t thrilled about Reagan’s policies, but he liked the way the former president acted—the very quality Trump had once criticized: “He’ll go down as a great president and not so much for the things he did. It’s just, there was a demeanor to him and spirit that the country had under Ronald Reagan that was really phenomenal. . . . There is a certain pomposity and there was a certain ribbon-cutting stature that is important for the president.” Trump said his main competitor for the Reform Party nomination, Pat Buchanan, was too divisive. Trump insisted he was all about inclusiveness. Who, King asked, would Trump pick as his vice presidential candidate? He named one possibility: Oprah Winfrey, the African-American talk show host who had asked him about presidential ambitions more than a decade earlier.
• • •
TRUMP’S SUGGESTION OF AN entertainer as vice president raised questions about whether this was all just one more publicity stunt. But Trump insisted this was a serious endeavor. He called himself a conservative but sounded like a liberal on many issues. In the Advocate, a gay-oriented newsmagazine, Trump took issue with how Buchanan talked about “Jews, blacks, gays, and Mexicans. . . . He wants to divide our country.” Trump called himself a conciliator, saying he would extend the Civil Rights Act to include protections for lesbians and gays and allow them to serve openly in the military, repealing Don’t Ask, Don’t Tell, the Clinton-era policy that had lifted a ban on gays in the military, but forbade them from talking about their orientation while in the service. Trump also called for universal health care and the protection of Social Security through a onetime tax on the superwealthy and new funds generated by renegotiation of trade agreements.
Two weeks after Trump announced his exploratory committee, he appeared on Meet the Press, where the moderator, Tim Russert, pressed him on a statement he had reportedly made about Clinton’s affair with Lewinsky: “When you say that if the president had had a fling with a supermodel rather than Monica, he’d be a hero—”
Trump interrupted, “But I didn’t say that. I said there are those that say that ‘if he had a fling with a supermodel, he would be everyone’s hero.’ I didn’t say that I said it.”
Trump, who had made countless appearances on friendly television venues, seemed unprepared for a grilling by a famously tough moderator such as Russert. Trump said he supported a right to partial-birth abortions, a late-term procedure that results in the death and intact removal of a fetus from the uterus. Stone, Trump’s political adviser, accompanied him to the interview. When the two left the studio, Stone said Trump admitted he didn’t know what a partial-birth abortion was.
In January 2000, Trump published The America We Deserve, which started with a blunt statement: “Let’s cut to the chase. Yes, I am considering a run for the presidency of the United States.” He said he wouldn’t run for “vanity” and said he would only enter the race “if I become convinced I can win.” Whatever happened, Trump wrote, he was certain that “nonpoliticians represent the wave of the future.” He also addressed his earlier comments to Russert: “When Tim Russert asked me on Meet the Press if I would ban partial-birth abortion if I were president, my pro-choice instincts led me to say no. After the show, I consulted two doctors I respect and, upon learning more about this procedure, I have concluded that I would indeed support a ban.” But what was his overall view? He said that while he was “uncomfortable” with abortion, “I support a woman’s right to choose.”
• • •
TRUMP’S QUASI CAMPAIGN TRAVELED to Minnesota for a January 2000 meeting with the role model Ventura. Trump and his wife-to-be, Melania Knauss, went to the penthouse of the Northland Inn in Brooklyn Park, a Minneapolis suburb, where a dozen members of Ventura’s election campaign awaited them. Trump told them he wanted to learn how a man who started at the bottom of the polls, who was deemed a joke by some, ended up as governor. How did he beat well-known politicians such as the mayor of St. Paul?
Dean Barkley, who had chaired Ventura’s campaign, advised Trump, “Just be honest. It’s not what you say, but how you say it. And talk to the public, not at them.” Phil Madsen, who ran Ventura’s online operations, told Trump how they used the Internet to solicit donations and spread their message.
Trump asked about the health of the Reform Party, given the fight between Perot and Ventura over its mission. Trump expressed concern about being a member of a party that included Buchanan and David Duke, the former Grand Wizard for the Ku Klux Klan. Trump wondered aloud if the differences were reconcilable. Barkley could offer little assurance that they were.
Later that afternoon, Trump and Ventura appeared at a lunch for the local chamber of commerce. Trump the listener was gone; the showbiz Trump had returned. He mocked the Republican candidates, winning laughs: “Are these people stiffs or what?” But Trump eventually chose not to run. On February 19, 2000, Trump wrote an op-ed in the New York Times in which he said that his exploratory campaign was the “greatest civics lesson that a private citizen can have.” He was not sure he would be able to win as a third-party candidate—especially one in a party beleaguered by such infighting.
But another seed had been planted. Indeed, although he had already pulled out of the race, Trump’s name remained on the Reform Party ball
ot in Michigan and California. He won both primaries.
• • •
WHILE TRUMP PULLED OUT of the arena, another politician was stepping in, in New York. Hillary Clinton was angling to be the US senator from Trump’s home state, and he seemed eager to support her. During her campaign for Senate in 2000, the First Lady had agreed to be the guest of honor at a fund-raising event for the New York State Democratic Committee. Judith Hope, the state party chairwoman, asked Trump if he would host the event at his Trump Tower penthouse. He told Hope he would be happy to do it as long as no more than fifty people attended. “No problem,” Hope responded.
On the evening of the event, 250 people showed up, crammed shoulder to shoulder, spilling drinks and food on the furniture as they jockeyed for photos with Trump and Clinton. A mortified Hope apologized to Trump, who graciously let it pass. Trump was registered as an independent at the time, but his politics were by now widely recognized as malleable, changing like a chameleon’s color to fit the moment. He seemed happy to stand next to Clinton and help out the state Democratic Party. Trump declined to say in an interview for this book whether he voted for Hillary Clinton, but said, “I felt it was an obligation to get along, including with the Clintons and including with a lot of other people. It was very important for me to get along with politicians in my business.”
Clinton won the Senate seat, and Trump continued to contribute to her over the next decade. He donated to Clinton’s campaigns six times, giving a total of $4,700 between 2002 and 2009. He also invited the Clintons to his wedding in 2005 to Melania. Hillary Clinton sat in the front row at the ceremony at Mar-a-Lago.
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