‘I’m Through’

The True Story of Donald Trump’s Florida Casino Fail

The Donald insisted during the CNN debate he never tried to bring casino gambling to Florida. Not only did he try—he failed spectacularly as his ex-protégé reaped more than $1 billion.

Photo Illustration by The Daily Beast

No wonder Donald Trump lied so vehemently during the Republican debate about not trying to introduce casino gambling to Florida.

The truth is he tried and failed.

Worse if you are The Donald, he was then bested by a onetime real-life apprentice whose firm went on to make more than $1 billion on gambling while Trump’s own gaming enterprise ended in bankruptcy.

Maybe Donald Chump, or rather Trump, was still trying to convince himself otherwise on Wednesday night when he declared at the debate, “I promise, if I wanted it, I would have gotten it.”

He also could have been seeking to protect the value of the Trump name. He had been asked during a 2010 bankruptcy proceeding what the Trump brand was worth.

“Over $3 billion,” he testified, that being a third of his supposed fortune.

The Trump name was prominently displayed on the private plane that landed in a Seminole Indian reservation back in 1996. Trump had not long before declared himself “the biggest enemy of Indian gaming.”

But he seems to have experienced a change of heart when it became apparent that somebody else might come along and form a lucrative partnership with the Seminoles should they secure permission to go into the casino business.

Trump arrived at the Big Cypress reservation airport with Richard Fields, a former talent agent who had once managed Trump’s second wife, Marla Maples. Fields was now viewed as a kind of business apprentice to The Donald. Trump and Fields watched a demonstration of alligator wrestling, sampled tribal fare at the Swamp Water Café, and met with Seminole chairman James Billie.

Billie—who is said to have been in danger of being killed at birth for being biracial—had become a recording artist as well as the tribe’s leader. Trump arranged for Billie to open for The Beach Boys at a charity concert at The Donald’s estate in Palm Beach. Billie reportedly brought along an alligator.

Trump also flew Billie and other Seminole eminences to his Taj Mahal casino in Atlantic City, where they were given front-row seats at a Rod Stewart concert. Trump made Billie a judge in the Miss Universe contest in Miami.

With his new pals the Seminoles, Trump retained lobbyist Mallory Horne, former speaker of the House and president of the Senate in the Florida state legislature, as well as a close friend of Florida’s then-governor, Democrat Lawton Chiles.

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Despite his pal’s lobbying, Chiles remained staunchly opposed to casino gambling. Trump figured he might do better with a leading Republican candidate to become the next governor, Jeb Bush. Trump held a $500,000 fundraiser for Bush at Trump Tower in New York and donated $50,000 to the Florida Republican Party.

Bush was elected in 1998, but any hope Trump may have had for a quid pro quo was dashed by a declaration the new governor made shortly after assuming office.

“I am opposed to casino gambling in this state, and I am opposed whether it is on Indian property or otherwise,” Bush said.

Fields had remained part of the casino gambling fight, and he continued on his own after Trump decided enough was enough. The lobbyist Horne would later recall in a sworn affidavit that Trump gave Fields his blessing.

“That’s the end of it,” Trump said of his own effort, as recounted in the affidavit. “If you want to try this on your own, Richard, that’s fine, but I’m through with it.”

Bush and the state legislature remained anti-casino, but the Seminoles and Fields eventually prevailed thanks to the U.S. Department of the Interior and the federal Indian Gaming Regulation Act. Fields and a Baltimore real estate development firm he had taken on as a partner were subsequently bought out by the Seminoles for more than $1 billion.

On learning of Fields’s success, Trump filed suit. Trump claimed that his former protégé had fraudulently used his name, leading people to believe he was still connected with The Donald.

No doubt Trump’s displeasure was intensified by his troubles in Atlantic City. The gambling venture he had begun in the early 1980s had gone through bankruptcy twice before Trump ended all financial or managerial involvement. He retained a particular personal stake as the company went broke yet again.

“My name is on the company and that’s very important to me,” he testified during the third bankruptcy proceeding.

In an unusual arrangement, Trump’s suit against Fields was tentatively settled as part of a $320 million deal by Fields’s firm to buy the Trump Marina and Casino in Atlantic City. Fields intended to turn the property into a Margaritaville-themed resort.

But the deal unraveled, with Fields reportedly dropping his offer down to $70 million. Fields continued to prosper, operating out of an office that is just a block up Fifth Avenue from Trump’s headquarters at Trump Tower.

If Fields is not quite The Richard, he was proof that The Donald had been just Donald Chump when it came to bringing casino gambling to Florida. That truth threatened to assert itself during the Republican debate.

“He wanted casino gambling in Florida…” Bush said.

“I didn’t,” Trump said.

“Yes, you did,” Bush insisted.

“Totally false,” Trump declared.

And the man with the $3 billion name almost seemed to believe his own cheap lie.