Tax records expose more than $21 million in highly unusual payments from the Las Vegas hotel Donald Trump owns with Phil Ruffin, routed through other Trump companies and paid out in cash.
Donald J. Trump needed money.
His “self-funded” presidential campaign was short on funds, and he was struggling to win over leery Republican donors. His golf courses and the hotel he would soon open in the Old Post Office in Washington were eating away at what cash he had left on hand, his tax records show.
And in early 2016, Deutsche Bank, the last big lender still doing business with him, unexpectedly turned down his request for a loan. The funds, Mr. Trump had told his bankers, would help shore up his Turnberry golf resort in Scotland. Some bankers feared the money would instead be diverted to his campaign.
That January, Mr. Trump sold a lot of stock — $11.1 million worth. He sold another $11.8 million worth in February, and $7.5 million in March. In April, he sold $8.1 million more.
And the president’s long-hidden tax records, obtained by The New York Times, also reveal this: how he engineered a sudden financial windfall — more than $21 million in what experts describe as highly unusual one-off payments from the Las Vegas hotel he owns with his friend the casino mogul Phil Ruffin.
In previous articles on the tax records, The Times has reported that, in all but a few years since 2000, chronic business losses and aggressive accounting strategies have allowed Mr. Trump to largely avoid paying federal income taxes. And while the hundreds of millions of dollars earned from “The Apprentice” and his attendant celebrity rescued his business career, those riches, together with the marketing power of the Trump brand, were ebbing when he announced his 2016 presidential run.
The new findings, part of The Times’s continuing investigation, cast light on Mr. Trump’s financial maneuverings in that time of fiscal turmoil and unlikely political victory. Indeed, they may offer a hint to one of the enduring mysteries of his campaign: In its waning days, as his own giving had slowed to a trickle, Mr. Trump contributed $10 million, leaving many people wondering where the burst of cash had come from.
The tax records, by their nature, do not specify whether the more than $21 million in payments from the Trump-Ruffin hotel helped prop up Mr. Trump’s campaign, his businesses or both. But they do show how the cash flowed, in a chain of transactions, to several Trump-controlled companies and then directly to Mr. Trump himself.
The bulk of the money went through a company called Trump Las Vegas Sales and Marketing that had little previous income, no clear business purpose and no employees. The Trump-Ruffin joint venture wrote it all off as a business expense.
Experts in tax and campaign-finance law consulted by The Times said that while more information was needed to assess the legitimacy of the payments, they could be legally problematic.
“Why all of a sudden does this company have more than $20 million in fees that haven’t been there before?” said Daniel Shaviro, a professor of taxation at the New York University School of Law. “And all of this money is going to a man who just happens to be running for president and might not have a lot of cash on hand?”
Unless the payments were for actual business expenses, he said, claiming a tax deduction for them would be illegal. If they were not legitimate and were also used to fund Mr. Trump’s presidential run, they could be considered illegal campaign contributions.