Donald Trump’s supporters are a collection of strange bedfellows. Among the most surprising: two billionaire financiers who teamed up against Mr. Trump in a legal battle less than a decade ago.
More than six years ago, investors Carl Icahn and Andrew Beal joined forces in bankruptcy court to try to take control of Trump Entertainment Resorts Inc., a deal Mr. Trump opposed. Now as some on Wall Street and in the Republican Party are trying to derail Mr. Trump’s campaign for president, the two billionaires are his most high-profile backers in the business community.
“There are no hard feelings,” said Mr. Beal, who endorsed Mr. Trump this past week. “He’s smart [and] gets things done.”
Mr. Beal, who founded Dallas-based Beal Bank and considers himself a libertarian, said he believes Mr. Trump will be pro-business and can bring “radical change” to Washington. One example: Mr. Beal said he recently sent Mr. Trump’s political-action committee a donation for $100,000. It was returned.
“I have never had a politician give me my money back,” said Mr. Beal in an interview. He previously backed Rand Paul, contributing $250,000, before the Kentucky senator dropped out of the race.
Mr. Beal’s reasoning overlaps with Mr. Icahn’s. The 80-year-old investor has called Mr. Trump an outsider who can help shake up politics, similar to how Mr. Icahn tries to change companies.
The men and real-estate investor Thomas Barrack Jr., who also endorsed Mr. Trump this past week, said the main reason they are backing the New York businessman is because they are exasperated with career politicians—and not necessarily because they agree with all of his policy positions.
Mr. Barrack, founder and executive chairman of Los Angeles-based Colony Capital Inc., said he didn’t think Mr. Trump would put into practice everything he has said on the campaign trail.
“He would adapt and come to logical conclusions…that’s my belief,” said Mr. Barrack, whose grandparents were Christian immigrants from Lebanon. “The rhetoric that seems harsh would dissipate.”
Their support for Mr. Trump contrasts with concerns from many in the business community, who have said the candidate’s economic ideas are impractical and his temperament unsuited to the presidency. Goldman Sachs Group Inc.
CEO Lloyd Blankfein last year said the image of Mr. Trump “with his finger on the button blows my mind.”
Lawyers for Messrs. Beal and Icahn also struck a different tone in 2009. In a court filing then, the lawyers contended that the Trump name may no longer be “synonymous with business acumen, high quality and style, a luxury lifestyle and enormous success.”
At the time, Messrs. Icahn and Beal were trying to take control of Trump Entertainment, which held properties in Atlantic City, N.J., after the company filed for bankruptcy, an effort that was ultimately unsuccessful.
The two men both say they remained cordial with Mr. Trump throughout the litigation. Mr. Beal has even attended at least one Broadway show with Mr. Trump.
“There was absolutely no animosity,” Mr. Icahn says today. “I respect him, and he made a good deal with [bondholders] and there’s nothing wrong with that.”
The Trump campaign, which is prone to hyperbole, last week called Mr. Beal “the most successful and wealthiest investor” in America.
Mr. Beal was ranked No. 115 on this year’s Forbes magazine list of the wealthiest people in world, which put his net worth at $9.9 billion. He called Mr. Trump’s description “extremely flattering” but said it was puffery.
When Trump Entertainment filed for bankruptcy again in September 2014, Mr. Icahn succeeded in gaining control and settled another suit with Mr. Trump, letting the Taj Mahal continue to carry the Trump name. The company emerged from bankruptcy late last month, and Mr. Trump lost his small stake.
In a news release this past week, the Trump campaign announced the endorsements from Messrs. Beal and Barrack. It quoted Mr. Trump as saying he was “proud to have their support” and also cited Mr. Icahn as a supporter.
Over the summer, Mr. Trump declared that he would like to name Mr. Icahn treasury secretary, much to the surprise of the investor who said at the time he didn’t know Mr. Trump was even running for president.
Mr. Icahn, a famous night-owl in business negotiations, turned down the offer, joking he doesn’t get up early enough for the job. But he expressed support for Mr. Trump’s candidacy. It was a rare endorsement for Mr. Icahn, who calls himself a centrist and has historically donated to candidates on both sides of the aisle.
The investor supports Mr. Trump’s push to stop the tax-driven deals that have U.S. companies fleeing to other countries for cheaper headquarters. And while he is a Wall Street trader, Mr. Icahn supports changing carried-interest taxes that help traders lower their tax bill on profits, saying that higher taxes for hedge funds could help shrink the wealth gap between the richest and poorest Americans.
In October, Mr. Icahn said he would launch a $150 million political-action committee, his first major foray into lobbying in politics.
In an interview at the time, Mr. Icahn said he immediately got pushback from fellow Wall Streeters, who angrily opposed Mr. Trump.
Mr. Barrack said in an interview that he has worked with Mr. Trump on a number of real-estate deals since the late 1980s, including selling him the famed Plaza Hotel in midtown Manhattan. Mr. Trump sold his interests in the hotel a few years later.
Before getting into real estate, Mr. Barrack served as a deputy undersecretary for the U.S. Interior Department in the Reagan administration.
Mr. Trump “has so many similarities to Reagan as an outsider,” Mr. Barrack said. “When Ronald Reagan ran, he was a cowboy, an actor from California. People said this was a joke.”
Yet Mr. Reagan surrounded himself with competent people, Mr. Barrack said. “I think Trump will do the same,” he added.
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