When Mr. Trump arrived in Washington in 1991, he and other developers were struggling, as he explained to the lawmakers.

“In the real estate business, we are in an absolute depression,” Mr. Trump said. The 1986 changes had been personally problematic for him, he said, suggesting that the more restrictive tax rules had compromised properties he had snapped up during that decade.

“They changed the game on me,” Mr. Trump said. In his offices, Mr. Trump confided, they had a new saying: “Survive until 1995.”

He raged against the real estate lobbyists sitting behind him in the hearing room, calling them “pathetic” for not beating back the earlier loophole closings. Congress, he said, should bring back the loopholes that had made the old tax shelters so popular.

“It is a very bad-sounding word, even though it isn’t necessarily a bad thing,” Mr. Trump said.

He even said that the recession had been caused by President Ronald Reagan’s 1986 tax overhaul — a conclusion few economists shared — and could be ended only by allowing investor dollars to flow easily back into real estate. Mr. Trump even argued against the very basis of the policy: The best way to get a recovery, he said, was to raise income taxes on wealthy people, to prod them to invest again in syndicated real estate deals.

“Donald Trump’s approach to solving this was, let’s go back to raising rates and opening loopholes so that we can syndicate,” said Steven M. Rosenthal, a senior fellow at the nonpartisan Urban-Brookings Tax Policy Center who worked on the eventual legislation as a congressional aide.

Mr. Trump — like his fellow real estate developers — did not get all he sought. But in 1993, Congress made two significant changes. One allowed real estate investors with highly leveraged properties to accept forgiveness of their bank loans without paying taxes on the money, in exchange for giving up other tax benefits. Another allowed them to apply some real estate losses against other kinds of income.