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.

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.”