Like Mr. Trump, Mr. Lo comes from a wealthy family. He is well known for creating a hip restaurant area in Shanghai called Xintiandi, or “new heaven on earth,” an upscale brand he has replicated across China. His life has been chronicled by tabloids and society pages, especially his divorce from his first wife and his marriage to a beauty pageant winner, Miss Hong Kong of 1977.

Despite their similarities, Mr. Trump hesitated when he received an invitation to travel to Hong Kong to negotiate the deal. He does not like to travel, and he feared that negotiating on the Hong Kong developers’ turf would put him at a disadvantage and make him appear weak, said Abe Wallach, Mr. Trump’s executive vice president of acquisitions and finance at the time.

But face-to-face meetings are crucial in Chinese business culture, where personal bonds and political connections, collectively known as guanxi, are relied upon to avoid and resolve business disputes, sometimes more than the legal system. Eventually, Mr. Trump’s aides convinced him that he had to make the trip.

In Hong Kong, the golf games, dinner parties and intensive talks featured the awkwardness and cultural miscues that can crop up in any high-stakes international negotiation. Mr. Lo and Mr. Cheng invited Mr. Trump to play golf, but Mr. Trump was appalled when they told him they usually bet more than $1,000 on each hole. They ended up betting $100 per hole, and Mr. Trump wound up losing more than he won, Mr. Lo recalled in an interview this month.

“He’s a good golfer, but we had the local knowledge — he probably was jet-lagged,” Mr. Lo said.

Mr. Lo and Mr. Cheng invited Mr. Trump to dinner at the home of Mr. Cheng’s father, an uncommon honor in Chinese culture. But the evening was a trying experience for Mr. Trump.

“He didn’t like the food, and couldn’t use chopsticks,” recalled Mr. Wallach, who was there. “The first course was a whole fish, with the head still on. You could see the face of the fish and the teeth, which really looked grotesque. The servant put the fish in front of Donald. Donald said, ‘The honor belongs to Abe.’ I took my chopsticks and began to pick at it.”