For years he's played a real-life game of Monopoly with such swagger that it seemed the stakes were play money. Now a cash crunch may force the tycoon to trade away his yacht, his hotels or his casinos.
Trump - whose name adorns everything from airplanes to board games, usually in large letters - may also have to wave arrivederci to the glitzy, fast-lane lifestyle he enjoyed during his rise in the 1980s.Creditors reportedly are pressing the multimillionaire for cash, and negotiations that are under way could compel Trump to sell huge chunks of his empire.
The real estate and casino magnate has a reported $2 billion in bank debt. His holdings, once estimated at $1.5 billion, had been sliced to $500 million, Forbes magazine reported last month.
The Taj Mahal, his centerpiece Atlantic City casino, is said to be for sale. The Trump Princess, his yacht, is on the block. The Trump Shuttle, his airline, is up for grabs.
On Monday, bondholders filed a lawsuit accusing Trump of promoting the Taj Mahal at the expense of the Trump Plaza and Trump Castle in Atlantic City.
Add to the equation his estranged wife, Ivana, who awaits her share with a $25 million prenuptial agreement that's looking better all the time.
"He'll have to trim the fat: get rid of the boat, the mansions, the helicopter," one banker involved in the Trump talks told The Wall Street Journal.
While this answers the question "What do you give the man who has everything?" - cold, hard cash - it raises another: what will Donald be left with? Trump: The Living Room Carpet? The Trump Motel and Drive-In Theater?
Trump, through spokesman Dan Klores, declined to comment further on the situation Tuesday. But The Donald never foresaw such problems in his first self-congratulatory book, "Trump: The Art of the Deal."
"I don't do it for the money. I've got enough, much more than I'll ever need," Trump wrote in the 1988 best-seller. As recently as April, the developer said he was selling off assets only to become "the king of cash."
Marvin Roffman was not swayed by such talk. The Philadelphia gaming analyst predicted problems for the Taj Mahal, and he said Trump had him fired for saying so.
Roffman, apparently vindicated by the reports of layoffs and losses at the palatial resort, bit his tongue Tuesday and cited a pending legal action. "My attorneys have cautioned me, and I really can't talk," he said.
The New York tabloids had no such concerns, and the rumors of impending financial crisis produced a round of entertaining Trump-bashing.
"Uh-Owe!" headlined the front page of the Post beneath a photo of Trump. Inside, the paper posed the question "The Taj: Eighth Blunder Of The World?" "Trump In A Slump" announced the Daily News.
"To me, Trump sounds about two steps away from selling used magazines on the sidewalk," wrote Daily News columnist Gail Collins. At least one expert felt she might not be too far off.
"Trump just thought the real estate market was heading upwards indefinitely and people would keep buying at higher and higher prices. He forgot that whatever goes up must come down," said Abe Wallach, an executive at the development firm First Capital Partners.
At the very least, his financial problems could postpone publication of Trump's latest laudatory book. Its unfortunate title: "Trump: Surviving at the Top."