SMALL TAX BILL
In 2016 and 2017, Mr Donald Trump paid just US$750 (S$1,030) in federal income taxes, according to the New York Times.
In 10 of the previous 15 years, he paid no federal income taxes at all.
Despite reporting hundreds of millions of dollars in income, Mr Trump effectively erased his tax bill by reporting heavy losses across his business interests.
Some of Mr Trump's most prominent real estate holdings have also been less than profitable, the Times reported. Mr Trump has reported a loss of over US$315 million on golf courses since 2000, with much of that centred on Trump National Doral near Miami.
The hotel he opened in the heart of Washington in 2016 has recorded more than US$55 million in losses, the report said.
An exception is Trump Tower in New York, which reliably earns him more than US$20 million in profits a year.
A BIG AUDIT
The Times report also found that Mr Trump has been feuding with the Internal Revenue Service (IRS) for the last decade over a nearly US$73 million tax refund he previously claimed.
If the IRS were to prevail in its audit, which has seemingly stalled in recent years, Mr Trump could be responsible for paying more than US$100 million to the government.
The Times also found that a large amount of Mr Trump's profits came from selling Mr Trump himself.
It reported that the former reality television star made a combined US$427.4 million from 2004 to 2018 by selling his name and image through various endorsements and licensing deals.
The Times said Mr Trump used proceeds of his celebrity to purchase and prop up some of his other businesses, including those which were losing money.
Mr Trump has been aggressive in claiming certain business expenses that further shrank his tax bill, according to the Times.
That includes US$70,000 in hair-styling expenses tied to The Apprentice, his former television programme, and classifying a New York property - described by the Trump Organisation as a family retreat - to be an investment property to write off millions in property taxes.
LOANS COMING DUE
In the 1990s, Mr Trump nearly ruined himself by personally guaranteeing hundreds of millions of dollars in loans, and he has since said that he regretted doing so.
But he has taken the same step again, his tax records show.
He appears to be responsible for loans totalling US$421 million, most of which is coming due within four years.
Should he win another term in office, his lenders could be placed in the unprecedented position of weighing whether to foreclose on a sitting president.
LARGE REFUND CRUCIAL TO TAX AVOIDANCE
Mr Trump did face large tax bills after the initial success of The Apprentice television show, but he erased most of these tax payments through a refund.
Combined, Mr Trump initially paid almost US$95 million in federal income taxes over the 18 years. He later managed to recoup most of that money, with interest, by applying for and receiving a US$72.9 million tax refund, starting in 2010.
The refund reduced his total federal income tax bill between 2000 and 2017 to an annual average of US$1.4 million.
By comparison, the average American in the top 0.001 per cent of earners paid about US$25 million in federal income taxes each year over the same span.