The banks could have easily toppled Mr. Trump into personal bankruptcy, "but we all agreed that he'd be better alive than dead," said Alan Pomerantz, then head of the real estate department at Weil. "We needed him to help sell all of his assets, and the deal was that as he sold off more, we'd reduce his personal guarantee." In effect, the banks allowed Mr. Trump to remain solvent so that they could get the benefit of his gift for salesmanship. In exchange, the banks provided him with $450,000 a month to operate his business and cover personal expenses. It was so tight a leash that when Marla Maples, his girlfriend at the time, turned up on television waving the costly Harry Winston diamond she'd been given as an engagement ring, the paymasters wanted a word with the groom-to-be. ..... < snip > ..... The banks shopped the Plaza around, without success, for a few years before finally selling it in a deal that valued it at $325 million to a partnership between Prince Alwaleed bin Talal of Saudi Arabia and CDL Hotels International of Singapore in 1995. None of the proceeds went to Mr. Trump, according to several people involved. Still, he told me that the sale was yet another victory. ..... < snip > ..... more than $3 billion in loans — $900 million of which were personally guaranteed — went into default. Dozens of banks came calling and, after lengthy negotiations, a meeting was held in a large conference room in the law offices of Weil, Gotshal & Manges, the firm that represented the largest lender, Citibank. There, some 50 bankers and lawyers watched Mr. Trump sign over nearly all of his properties — the Plaza, other buildings, the shuttle, the yacht, the jet — in exchange for more favorable terms on his personal guarantees.
From The Backstory on Donald Trump's Four Bankruptcies - TSC, by Emily Stewart, 2015 September 15
..... Four years later, Trump and Ivana had split, and the hotel had millions of dollars in debt. ..... < snip > ..... In November 1992, the now-billionaire filed for bankruptcy protection for the Plaza after the hotel was unable to meet its debt service payments. A month later, federal bankruptcy judge Prudence Abraham approved a plan for Trump to reorganize more than $550 million in debt. As part of the restructuring and to receive easier payment terms, he gave a 49% stake in the property to Citibank (C) and five other lenders. He kept his post as chief executive — without pay — and no longer had a role in the day-to-day operations of the luxury hotel. Three years later, in 1995, Trump made a deal to sell the Plaza to Singapore-based international property and hotel conglomerate CDL Hotels International and Saudi Arabian Prince Walid bin Talal. The deal largely entailed buyers paying off most of $300 million owed to creditors, according to the New York Times. The last $25 million was to be converted to equity held by a Citibank-led consortium, and the buyers also agreed to pay down the first mortgage on the property, held by the Industrial Bank of Japan. 1992, Plaza Hotel
From By the Numbers: Donald Trump's $4.7 Billion in Bankruptcies - DR, by Jimmy Atkinson, 2015 July 30
Shortly after striking a deal on the Taj Mahal, Trump returned to bankruptcy court when he was unable to cover the interest payments related to a prominent Manhattan hotel. In 1988 Trump bought the Plaza Hotel, which overlooks Central Park, for approximately $390 million. That price tag represented an increase of more than 1,500 percent from the $25 million paid for the property just 13 years earlier by the Westin Hotel company. ..... < snip > ..... by 1992, the hotel's cash flows were insufficient to cover the interest on some $550 million in debt related to the purchase and subsequent renovations. Trump filed for bankruptcy in November 1992, and about five weeks later a judge approved a plan that called for Trump to give up 49 percent of his ownership in exchange for group of creditors included Citigroup and the Industrial Bank of Japan. As part of the restructuring, Trump stayed on as CEO of the hotel but was not paid a salary and did not have a role in the day-to-day operations of the hotel. Three years after filing for bankruptcy, Trump sold the Plaza for $325 million to a group that included a Singapore businessman and Saudi Prince Alwaleed bin Talal. Trump remained a minority partner in the hotel following the sale, but didn't see a dime from the sale. Proceeds from the sale went to paying down the debt held by banks, which was reduced from about $300 million to $25 million. The remainder of the debt was converted into an equity stake. In 2012, Indian conglomerate Sahara Group paid $570 million for a 75 percent stake in the Plaza. ..... Bankruptcy #2: Plaza Hotel in 1992
..... Ultimately, the value of Trump's ownership stake in the reorganized companies was worth very little: Though Trump did receive $40.5 million when the post-bankruptcy Taj Mahal was sold, it came in the form of stock in THCR — which ultimately experienced multiple bankruptcies of its own and today is close to worthless.