The day Donald Trump called and asked for a one-on-one meeting in the winter of 1988, Tom Barrack was a relative newcomer to the high-stakes poker game of New York real estate. He had worked for nearly two years for Robert Bass, the Texas billionaire investor, and had played an important role in winning the Plaza Hotel for his boss the year before. Mr. Trump was the country’s most quotable and ostentatious financial celebrity, a guy with a jet, a 282-foot yacht and a fondness for peach-toned marble.

But among the people he negotiated with, Mr. Trump had a reputation for both steeliness and finesse. So Mr. Barrack was wary. A mere four months after Mr. Bass had taken control of the Plaza, he gave Mr. Barrack the go-ahead to put it up for auction. Mr. Trump was calling to say, in effect, skip the auction. We’ll strike a deal, the two of us, right here in my office.

“Just come over,” Mr. Trump said, in Mr. Barrack’s recollection. “Give me half an hour.”

Mr. Barrack was soon sitting in Mr. Trump’s office in Trump Tower on Fifth Avenue. The two had met a few times, because Mr. Trump had been angling to acquire the Plaza for years. Now that it was going back on the market, Mr. Trump didn’t want to miss out.

“How can I live without it?” Mr. Trump asked, gesturing to the Plaza, which could be seen from his window, just two blocks north. “It’s right in my backyard.”