What he got instead was a New York brawl with a group of tenants fighting to save their homes and clinging with white knuckles to some of the city’s legendary rent deals. The battle played out for years in courtrooms and the New York news media, becoming a kind of parable of the limits of 1980s capitalist ambition in the social democratic city.

Looking back on the fight, on the eve of Tuesday’s New York Republican primary, one can see Mr. Trump waging a much different sort of campaign, but with many of the same tactics — the threats, the theatrics, the penchant for hyperbole — that he has deployed in his quest for the Republican presidential nomination.

As far as the tenants are concerned, Mr. Trump lost that contest.

“Oh, absolutely, we won,” said Ms. Rubinstein, sitting in the one-bedroom apartment where she still lives. “He wanted this whole corner to be one big Trump building.”

But Mr. Trump refuses to admit defeat.

“A great deal,” he said, without hesitation, when describing 100 Central Park South — now known as Trump Parc East — during a phone interview last week. “It was a long battle, but it was a successful battle. As usual, I came out on top.”

Mr. Trump paid just $13 million for 100 Central Park South and the building adjoining it, the Barbizon Plaza Hotel, in 1981. At the time, he was 35 and making bold strides to emerge from his father’s shadow. In recent years, he had built the 68-story Trump Tower and overhauled the building near Grand Central Terminal that became the Grand Hyatt New York.