In 1991, however, it was Trump's lunch that was eaten by a foreign competitor, when the real estate mogul, in debt to the tune of $900 million, ceded his 281-foot super-yacht Trump Princess over to creditors.
The yacht was then purchased by Prince Alwaleed Bin Talal Bin Abdulaziz al Saud, mogul and member of the Saudi royal family. He also happens to have a stake in another forsaken Trump property: the Plaza hotel in New York.
The Donald had a strange affinity for the swanky yacht he purchased in 1988 from the Sultan of Brunei for $29 million, which at the time was one of the largest in the world. According to former Trump executive John R. O'Donnell, the real estate mogul sailed on it only once, its maiden voyage from the Azores to the New York harbor.
"It so terrified him when they weighed anchor -- the movement convinced him it was sinking -- that he would never sleep on it," wrote O'Donnell in his book Trumped!. "All the time it was docked at the marina, he went on board only to watch boat races or occasionally to entertainment important customers or business associates."
Still, he wrote, "Donald took pleasure in showing off the boat."
President Ronald Reagan even sent a telegram of congratulations on the boats docking.
In his book, Surviving at the Top, ironically released while The Donald was in the midst of massive debt, there's a chapter entitled: "Ship of Jewels: The Trump Princess."
And it was during this time that Trump had to sell the property.
"Faced with massive debts and increasing cash-flow problems, Trump has been forced to get rid of large chunks of his empire to stay afloat. Among properties he is ceding to creditors are his 282-foot Trump Princess yacht, a 49% stake in New York's Grand Hyatt Hotel, the Trump Shuttle airline and his 27% stake in Alexanders Inc., a department store chain," read a Reuters story in 1991 on Trump's restructuring of his considerable debts.
"I bought the boat in the high 20s. I sold the boat essentially for the mortgage that was on the boat. Forty to forty two million, that was the amount of the loan that was on the boat," The Donald told the Boston Herald in 1991 when they heard his boat repossessed by mortgage-holder Boston Safe Deposit & Trust Co.
Trump told the Herald it was "totally incorrect," he was behind on his payments and he said the transfer of the yacht was "friendly." From there, the boat made it's way to Alwaleed.
Today, the boat renamed "Kingdom 5KR," docks in France.
The Trump Princess wouldn't be the last property that Alwaleed came to hold. He would take a controlling stake in the Plaza in 1995.
"The deal is subject to approval by the consortium of banks, led by Citibank, that has controlled the Plaza since 1993, after Trump was unable to make loan payments," wrote Newsday in 1995 on the properties sale.
Since the 1995, Alwaleed's stake in the Plaza has varied over the years.
Earlier this year, Trump tweeted at an Alwaleed parody account, "Saudi Arabia should be paying the United States many billions of dollars for our defense of them. Without us, gone!"
Alwaleed's son, Khaled bin Alwaleed, replied, " lol wrong Twitter user. Just FYI."