He lost enough money that he didn't have to pay income taxes in eight of the 10 years the Times studied.
The numbers show that in 1985, Mr. Trump reported losses of $46.1 million from his core businesses - largely casinos, hotels and retail space in apartment buildings. This is known as a net operating loss, and by 1991, the Times says, Trump's net operating losses had grown to nearly $418 million, or 1 percent of all the losses reported to the IRS by individual taxpayers that year.
Fox News contributor Newt Gingrich defended President Donald Trump from what many see as a very damning New York Times report that outlines in grave detail, just how financially unsuccessful Trump's business dealings were from the mid-80s to the mid-90s.
He has yet to officially comment on the report.
President Trump and his family are suing Deutsche Bank and Capital One, two financial institutions with which they have had dealings, to block them from releasing any information about his tax or finances.
Milwaukee Bucks: 3 takeaways from big Game 4 win vs. Celtics
In a decisive Game 1 win against Milwaukee, the Celtics offered a clinic on how to defend Giannis Antetokounmpo . He set the tone for them, I think when he came in, they were playing harder and they were moving the ball.
Senator Chris Coons, a Democrat from DE, said the report showed Mr Trump "failed spectacularly" in business during that time frame. It said he may have lost more than any other American. Under the tax code, business owners can use their losses to keep from paying taxes on future income. The left-leaning Daily News splashes the story on its cover with a headline, "Biggest Loser", borrowed from Trump's old reality TV milieu.
Upon being elected, the president has broken with decades of precedent and has not released his tax filings.
Several weeks ago, a senior White House official told the Times, "The President got massive depreciation and tax shelter because of large-scale construction and subsidized developments".
The Times quoted a lawyer for the president, Charles Harder, as saying the tax information was "highly inaccurate".
Pelosi said Democrats may "go directly to court" to challenge the refusal, and joked about suggestions that they have the treasury secretary, Steve Mnuchin, arrested for refusing to hand over the documents.