Ben Schreckinger is a reporter for Politico.

After sending mixed signals about what might drive him to withdraw from the presidential race, Donald Trump settled on a definitive answer last month: “I’m never dropping out.”

The next day, he tweeted, “I’m leading big in every poll and we are going to WIN! Remember, Trump NEVER gives up!”


But, like many successful businessmen, the real estate developer and GOP pack leader—who often espouses his disdain for “losers”—does not see every venture and contest through to the bitter end. Throughout his career, Trump has demonstrated wild enthusiasm at the start of big projects, and ruthlessly pursued a profit agenda that, in many cases, has led him to ditch the deal when the risks, whether financial or reputational, start to outweigh the prospective reward.

From a casino in French Lick, Indiana, to a dispute with condo owners in Panama and even in renewing “The Apprentice” reality show on NBC, Trump has time and again spotted the point of diminishing returns and quit.

This business record could shed light on Trump’s willingness to fight on and put more of his personal fortune on the line as the presidential contest shifts into the primary phase. In national polls, he’s already come down several points from his September peak, and Ben Carson has risen to within striking distance. Should Trump fall from first place or find himself in the middle of a protracted dogfight for the nomination, the complications and cost associated with a winning campaign organization would expand. And that could change his calculations.

“He expects to win the nomination and is in it to the end,” says campaign spokeswoman Hope Hicks.

But the Trump Organization’s general counsel, Alan Garten, has a more nuanced take. “If he’s not going to win the primary, then why would he continue to use up his own time and resources?” says Garten, adding, “If he’s not going to win the nomination, then he’ll go back to running his successful business. To me that’s a testament to what he’s built.”

And what he has built is vast and wealth-producing. Indeed, it’s his sprawling portfolio of projects with multiple revenue streams and profile-raising opportunities that is supporting his 2016 run. So far, the return on investment has been strong.

Trump’s third-quarter Federal Election Commission disclosures reveal he has contributed only about $100,000 out of pocket to his campaign, on top of a $1.8 million loan that can be paid back to him at any time. Rather than spend millions on consultants, advertising and polling, as other top candidates have, he has organized his candidacy around his celebrity, giving him the opportunity to secure free airtime across television networks, draw large crowds to arenas for rallies and avoid the costly endeavors that swallow up most of a traditional campaign’s funds. And the result has been a first-place spot in nearly every national poll for three months.

But the 2016 campaign enters a new season this quarter, one that’s as much about ballot access and ground game as airtime. Trump might find a greater personal investment necessary to win. And what’s clear from his business dealings is that when that investment starts to sour, he cuts bait.

That’s what happened in French Lick, Indiana.

The Indiana Gaming Commission awarded Trump a contract to build a casino in 2004, and the town rejoiced. A band at the French Lick Springs Resort & Hotel struck up “Happy Days Are Here Again” as townspeople celebrated over beer and hot dogs. “It’s like Christmas in July,” one local advocate of Trump’s bid told The Associated Press.

The name of the former Trump Plaza casino in Atlantic City, N.J. is spelled out in dirt on the facade of the shuttered casino three months after work crews removed the letters from the building. | AP Photo

For a once-glamorous resort town that had fallen on hard times, the victory was not just in the prospect of building a new economic engine. It was in Trump’s involvement. “The idea of having an internationally known name on that casino was very enticing,” says Jenny Reske, deputy director of the commission.

But Trump never built the casino.

That fall, on the eve of a November bankruptcy filing, Trump Hotels & Casino Resorts assured the state that its plans for French Lick remained on course. But the project’s prospects grew dimmer when newly elected Gov. Mitch Daniels, alarmed by the state of the company’s finances, called for a review of the deal. In January 2005, he called for the state commissioners who approved it to resign.

Trump, though, was not about to be fired. In March, before the state review was completed, he quit.

His company withdrew from French Lick and issued a statement citing a recent Indiana court ruling that another Trump casino in the state owed $18 million in back taxes. “The financial prospects for a casino in French Lick have changed since the time we were awarded the project,” it said.

Residents of French Lick, says Reske, greeted the withdrawal with “disappointment.”

Trump would not let himself be fired in 2007 either, when NBC left “The Apprentice,” which was struggling with low ratings, off an initial prime-time schedule. The omission prompted rumors of the show’s demise, and Trump quickly issued a statement saying that he was “moving on from ‘The Apprentice’ to a major new TV venture.”

The Reuters headline—“Donald Trump to NBC: ‘You can’t fire me, I quit’”—wrote itself.

Trump and the network reached a deal to resurrect the series at the eleventh hour, its ratings improved and the mogul continued to host the show until he embarked this year on a presidential run—a run that has exploited Trump’s celebrity to conduct a low-cost campaign fueled by free media and unsolicited donations, allowing him thus far to avoid sinking much of his personal fortune into the bid.

Similarly, for the past decade, Trump has capitalized on his worldwide fame to close low-risk licensing deals that allow him to collect fees for lending his brand to developments without sinking significant capital into the projects. “What made that a brilliant move is that it limited his exposure and limited his liability,” Garten says.

When several of those developments went bust amid the collapse of real estate markets that began in 2007, the business model allowed Trump to walk away relatively unscathed, and in some cases turn a profit. It also tied Trump’s brand to projects he touted before they failed.

Trump Ocean Resort Baja, for one, was going to be “one of the finest resorts in all of Mexico.” It was going to “exceed all expectations of luxury.” Donald Trump said he had visited the site himself twice and that he would be a “significant” equity investor.

A 2006 article in the San Diego Union-Tribune stated: “Having recently lent his name to a line of vodka, Trump insists he’s doing more than just branding a real estate development. He says that The Trump Organization will be a ‘significant’ equity investor in the $200 million project.”

Then the real-estate bubble burst. It turned out Trump had not become an equity investor; he was merely a licenser. He said he had never visited the site of the project. “I have never been there,” he told the Union-Tribune of the project in 2009. “They licensed my name.”

The investors sued Trump, his daughter Ivanka, his son Donald Jr., the Trump Organization and Jason Grosfeld, the developer Trump partnered with, alleging fraud, among other claims, for misrepresenting the Trumps’ involvement in the development. Grosfeld paid out $7 million. Trump, Ivanka, Donald Jr. and the Trump Organization settled on terms that were undisclosed, but Bart Ring, the attorney who represented investors in Trump Baja, says his clients were “very pleased” with the outcome.

Trump’s counsel, Garten, says that at the time Trump made his initial statements to the Union-Tribune he was considering a significant equity investment in the project, and that the plaintiffs’ claims were baseless. He says settling the suit “made great financial sense.”

It also spoke to Trump’s ability to calculate the return in fighting, something as relevant to his political career as his business one.

“Will he stay in it until the end? Maybe he will,” says Ring. “In the transaction our clients were involved in, he did not follow through on what he said he would do and had no problem going back on his word.”

A billboard at the construction site of Trump Ocean Resort Baja reads "Trump. Owning here is just the beginning." | AP Photo

Garten says he does not believe Trump’s statements about never quitting the presidential race should be evaluated in the light of his business career. “Trying to connect those two points is a big stretch,” he says.

French Lick, “The Apprentice” and Trump Baja are not isolated cases. Trump consistently shows a willingness to exit losing propositions.

In 1999, after trying for years to turn a steady profit at the struggling Trump World’s Fair hotel and casino in Atlantic City, the businessman gave up and shuttered the property.

By the end, it was losing $10 million a year, according to The Associated Press. At the time, Trump said he was not abandoning the site. The AP reported that he planned to spend $750 million rehabilitating the property. But he never did. Months later, panes of glass began falling from the deteriorating structure, prompting the temporary closure of parts of the city’s boardwalk, according to the AP.

Six years later, Trump’s casino company auctioned off the property as part of its bankruptcy process, and Trump himself put in a bid to regain control of the site. Another developer, Bruce Toll, outbid him.

In 2013, Toll announced plans for a mall there. By then, Trump had totally bailed on Atlantic City, a loss-minimizing decision he touts regularly on the presidential stage.

In a separate Atlantic City case, in February 2009, Trump Entertainment Resorts, the successor to Trump Hotels and Casino Resorts, faced the prospect of involuntary bankruptcy. After bondholders rejected Trump’s proposal to purchase the company, he resigned as chairman of its board. Days later, the company filed for bankruptcy.

“He felt like among other things that they were not representing his brand the way it should be,” explains Garten, who pointed out that Trump made huge profits in Atlantic City before getting out.

And this summer, when the residents and owners of condominiums at the Trump Ocean Club in Panama attempted to end their relationship with Trump Condominium Management LLC—claiming that the company was making unauthorized expenditures—the Trump Organization wrote back to say it could not be fired. Instead, it was quitting, claiming breach of contract, and demanding a $5 million termination fee, as the AP reported this month.

Garten says the Ocean Club owners had not heard the last from Trump. “We’re going to be proceeding against them because they now owe us millions of dollars,” he says.

There were also Trump’s tower projects in Dubai, Mexico, Fort Lauderdale and Tampa—all similar to the Baja resort project in that he sunk little of his own money into the ventures, though he did invest his time and reputation in marketing them. Trump International Hotel & Tower in Dubai, for instance, was announced in 2005 as a partnership with local developer Nakheel Properties.

“My project with Nakheel will be one of the most impressive undertakings I have ever been a part of,” Trump said in a June 2008 news release announcing that he planned to reserve a residence in the building and that its penthouse would be the most expensive apartment in Dubai. “I can assure you that the hotel will be a destination in itself, providing a stunning centerpiece to the skyline of Dubai.”

To trumpet the project, Trump threw star-studded parties in New York and Los Angeles in the summer of 2008. At the Los Angeles party, Christina Aguilera performed. “We just love Christina, and I’ve been with her many times,” Trump told the Los Angeles Daily News at the time. “But not in a sexual way—though I wish, I wish.”

In December 2008, the project was suspended and in 2011 it was permanently cancelled.

Trump towers in Fort Lauderdale and Tampa, Florida, were also cancelled when the real estate bubble burst, resulting in a flurry of lawsuits and sore feelings from investors who said they lost their deposits and felt misled by a man they had revered. In Fort Lauderdale, one group of investors lost its suit against Trump and was forced to pay court costs.

Garten points to projects in Las Vegas and Chicago developed by the Trump Organization that did come to fruition despite difficulties related to the 2007-08 financial crisis.

Nonetheless, Trump’s ability to spot a coming decline and bank his profits before the fall is notable.

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“Mr. Trump has the greatest vision and was able to predict the market collapse and therefore did not build. He has been tremendously successful at predicting markets and will apply this mentality to the country,” says Hicks in a statement. “This handful of projects should be used as evidence as to why Mr. Trump will make a phenomenal President. He has unparalleled vision and leadership skills that will Make America Great Again.”

It’s also evidence that Trump knows when the end might be near.