On Capitol Hill, some Democrats renewed calls for Trump to release his tax returns - which he has repeatedly declined to do, unlike his predecessors.
"I knew there had to be a compelling reason why this president departed from previous presidents in not disclosing his income tax returns," said Sen. Richard Durbin, Ill., the Senate's second-ranking Democrat. Asked whether it merited a new push to reveal Trump's personal financial records, Durbin said: "Yes."
The president's company, the Trump Organization, did not immediately respond to requests for comment. The White House issued a statement late Tuesday that called the Times story misleading. "Many decades ago the IRS reviewed and signed off on these transactions," the statement said, before touting Trump's economic policies and his success at making trade deals. The White House earlier referred questions to Charles Harder, a private attorney for Trump. Harder's office did not respond to questions from The Washington Post.
In a statement to the Times, Harder wrote that its findings were "100 per cent false, and highly defamatory."
"There was no fraud or tax evasion by anyone," Harder told the newspaper. "The facts upon which The Times bases its false allegations are extremely inaccurate."
Trump spent decades guarding the secrecy of his real estate, golf and hotel company - making it difficult to check the stories he told about his own success.
As president, he now faces a growing number of investigations into his private business and personal finances.
The New York attorney general sued him in June, saying Trump allowed "persistently illegal conduct" at his charitable foundation. Democratic attorneys general and congressional lawmakers are prying for details about the Trump Organisation's transactions with foreign governments as part of two separate civil suits. Special counsel Robert Mueller III has delved into the Trump Organization's business dealings with Russia. And the U.S. attorney in Manhattan is investigating Trump's involvement in hush-money payments made to adult-film star Stormy Daniels.
The Times story could spark a new line of investigations from state authorities in New York and possibly from Congress, if Democrats take control of either chamber in November's elections.
"We must see Trump's tax returns to know just how far and how deep the crimes go," Rep. Bill Pascrell Jr., D-N.J., a member of the House Ways and Means Committee, said in a statement. "This Trump exposé paints a portrait of a man whose entire professional life was built on his father's money, skirting accountability, and 'outright fraud.' "
The IRS did not immediately respond to requests for comment. Officials with the New York Attorney General's Office and the Manhattan District Attorney's Office declined to comment.
The Times investigation contradicts the image Trump has projected of himself for decades, as a self-made billionaire who inherited a small sum and amassed his own fortune through smarts and grit.
On Tuesday, one former White House official who spoke on the condition of anonymity to speak candidly said Trump will "freak out" about the piece because he has been so protective over the years about what the ex-official termed "his own financial legend."
"There probably is nothing more painful and upsetting to Donald Trump in the world than the suggestion that he is not as rich as he says he is and as responsible for being rich as he says he is," said Tony Schwartz, who co-authored Trump's mythmaking book, "The Art of the Deal," in 1987.
"On the scale of things that would enrage him, this [Times investigation] would rate very, very highly," he added.
Trump keeps just two family portraits in the Oval Office: black-and-white photographs of Fred Trump and Trump's mother, Mary. From the front, it appears they are peering over their son's shoulders as he sits at the Resolute Desk.
Fred Trump was a Queens-based developer who made a fortune building drab but serviceable low-rise apartment blocks for a fast-growing city. When Donald Trump tells the story of his own origins in business, he often emphasizes that he was a self-made man - who didn't need, or get, much help from his father.
"My father gave me a very small loan in 1975, and I built it into a company that's worth many, many billions of dollars," Trump said during a 2016 presidential debate.
The Times story says that account is false - that, in reality, Fred Trump spent decades quietly ceding his fortune and his business empire to his son, in ways that seemed designed to avoid taxes on gifts and inheritance.
The Times story identifies several avenues through which Fred Trump's wealth was passed to his children. Among them:
- The family created a business, All County Building Supply & Maintenance, which was supposed to be a middleman between Fred Trump's company and its vendors. Then, the story said, Fred Trump's company overpaid All County for those services, based on phony, inflated invoices, and All County kept the difference.
- In December 1991, Fred Trump sold his 7.5 per cent stake in the Trump Palace condominium building on Manhattan's Upper East Side to his son. The stake was worth about $15.5 million, the Times said, but Donald Trump bought it for just $10,000 - allowing his father to dodge millions in tax liability.
- In the years before his father's death, the Times said, Donald Trump participated in an effort to systematically lower the appraised values of Fred Trump's buildings. That included dividing their ownership among a series of new companies to give the impression that Fred Trump did not control them.
The Times described these machinations as the "alchemy of turning real estate that would soon be valued at nearly US$900 million into US$41.4 million."