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, 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, 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 Phil Ruffin, the casino mogul.

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 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’ continuing investigation, cast light on Trump’s financial manoeuvrings 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, 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 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 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 Trump’s presidential run, they could be considered illegal campaign contributions.

In response to questions about the Times’ findings, a White House spokesman, Judd Deere, referred to this article as “yet another politically motivated hit piece inaccurately smearing a standard business deal.” He added that “during his years as a successful businessman, Donald Trump was longtime partners with Phil Ruffin and earned whatever payments he received.”

A spokeswoman for Ruffin, Jennifer Renzelman, said Ruffin was not involved in the day-to-day operations of the hotel, adding that “all tax statements go to the people who work on his taxes.”

It is fair to say that, over the years, Ruffin has been very generous to his friend. When Trump took the Miss Universe pageant to Moscow in 2013, the two men flew over together on Ruffin’s private jet. He would contribute more than $2.5 million to Trump’s campaign, his ill-starred foundation and his inaugural.

And after the inauguration, Ruffin would ask for a favour. Would the president help revive a dormant project of great importance to a lot of powerful people in Las Vegas — a bullet train that would whisk gamblers from Southern California to The Strip in less than 90 minutes?

Four years earlier, Barack Obama’s administration had considered, but ultimately decided against, a $5.5 billion loan for the train. Trump loved the idea, Ruffin told Forbes in a 2017 interview.

This past March, a panel composed largely of Trump appointees gave the train company permission to sell $1 billion in tax-free bonds to private investors. Authorities in California and Nevada fell in line, approving additional bonds. Trains could begin running as soon as 2024.

Among the train’s chief beneficiaries will be Ruffin and the other grandees of gambling who became a vital font of political money for Trump when he needed it most.

And, of course, Trump himself.

A Friend of the President

In business, Ruffin was a kindred spirit: a wealthy transplant to Las Vegas from Kansas. In politics, he would be crucial cheerleader.

Ruffin’s patronage of the president has been less lavish, and less examined, than that of his Las Vegas compatriot Sheldon Adelson. But he has long been a wingman for Trump’s political ambitions — urging him to run, burnishing his image and promising financial support.

In July 2016, he took the podium at the Republican National Convention in Cleveland to sing the nominee’s praises.

“Donald’s word is his bond. If Donald tells you something, you can put it in the bank,” he said. “I love the man.”

Ruffin loved the man so much that when Trump was considering a White House run back in 2011, he donated the venue for a Las Vegas rally: a ballroom at his Treasure Island Hotel and Casino. After Trump decided that he would indeed run, in 2015, it was at another Treasure Island rally that Ruffin expounded on his friend’s charitable good works.

Also in 2015, Ruffin gave $1 million in seed money to the Make America Great Again super political action committee, only to have it refunded when the group was dissolved after news reports that it had improperly coordinated with the Trump campaign.

The two men had been brought together in the early 2000s by Ruffin’s belief that his business needed some Trump-branded glitter. Trump, whose Atlantic City casinos were flailing, was looking to expand to Las Vegas. The result, built on the former site of a mall parking lot: a “64-story tower of golden glass” that “soars above The Strip,” according to the hotel website.

Plus, a friendship between men from very different places but with parallel trajectories: Trump to boldface-name Manhattan from “outer borough” New York; Ruffin to Las Vegas from Wichita, Kansas, where he had become wealthy as a pioneer in self-service gas stations and as owner of the world’s largest manufacturer of hand trucks.

It was Trump who introduced Ruffin, now 85, to his third wife, Oleksandra Nikolayenko — like Melania Trump, a much younger former model. In 2004, Nikolayenko represented Ukraine at the Miss Universe pageant. The couple were married in 2008 at Mar-a-Lago, Trump’s private club in Palm Beach, Florida, with him as best man. The men’s wives are quite close, Ruffin has said, “like peas in a pod.”

When he flew Donald Trump to Moscow for the 2013 edition of Miss Universe, Ruffin also became a bit player in an episode that would, over time, spawn some intrigue and much speculation. Investigations into Kremlin interference in the 2016 election would detail how the president’s Russian partners in the pageant wooed him and then helped broker the meeting where Donald Trump Jr hoped to get “dirt” on Hillary Clinton. The partners’ willingness to underwrite the entire pageant made it Donald Trump’s most profitable Miss Universe. His personal payday, according to his tax records, was $2.3 million.

A report from the Senate Intelligence Committee this August, looking extensively at the pageant, included a “Dear Phil” letter sent by Trump days after the event.

“It was great spending time with you in Moscow and making the rounds of the city in the hopes of the purchase or development of a project,” Trump wrote, before concluding, “Let’s see how it all turns out — it is important that we make a good decision.”

Other People’s Money

The campaign was strapped for cash, and many big donors still weren’t sure about Trump. Then Las Vegas came around.

On the campaign trail, Trump frequently boasted that he was so rich he did not need other people’s money. As president, he promised, he would be beholden to no one.

“He’s driving me crazy,” Trump said of Ruffin at a February 2016 rally after winning the Nevada caucuses. “He said, ‘Donald, I want to put $10 million into your campaign.’ I said, ‘Phil, I don’t want your money. I don’t want to do it. I’m self-funding.’ Every time I see him, it’s hard for me to turn down money, because that’s not what I’ve done in my whole life. I grab and grab and grab.”

In fact, he needed Ruffin’s money, and then some.

Trump had promised to pour $100 million of his own money into the campaign, but after an early infusion of more than $35 million in 2015 and early 2016, the flow eventually slowed to a steady $2 million or so near the end of each month. What was at first described as a series of loans became a donation amid the politically uncomfortable perception that the populist billionaire was hoping to have his grassroots supporters pay him back.

For even as his campaign was building its vaunted internet-powered small-donor operation, much of the Republican fundraising establishment hung back, still stunned that Trump had emerged as the party’s standard-bearer. At the low point, in June, the campaign had just $1.3 million in the bank, according to its financial disclosures.

After the convention, the Republican National Committee began pulling in its traditional big donors, but the Trump fundraising machine still sputtered heading toward Election Day, especially after the release of the “Access Hollywood” tape that showed Trump bragging about groping women.

Then, on Oct 28, came his surprising $10 million contribution. (That brought his total spending to more than $60 million.)

It was in those final, decisive weeks, too, that the weight of Las Vegas fell in behind him.

After months of hesitation, Adelson — gambling magnate, Republican megadonor and strident voice for Israel — became the candidate’s biggest contributor. Often along with his wife, Dr Miriam Adelson, he donated $20 million to Trump’s campaign and political action committees supporting it. He later gave $5 million more to the inaugural. The Las Vegas Review-Journal, which he had recently purchased, gave Trump a rare newspaper endorsement.

Others gave, too, including the Fertitta family, owners of casinos and the Ultimate Fighting Championship, who contributed more than $1.5 million. Steve Wynn, the candidate’s old Atlantic City casino rival, moved over to the friend column after the election, giving $729,217 to the inaugural and becoming the finance chairman of the party. (He resigned in 2018 amid a sexual assault scandal.)

As for Ruffin, he didn’t give the $10 million that Trump had complained was driving him crazy. But he and his wife did contribute almost $1.6 million during the campaign and to the inaugural. And he gave another $1 million in 2016 to Trump’s foundation before it shut down amid an investigation into allegations of self-dealing.

Moving the Money

After draining much of the cash he had on hand, Trump received more than $21 million in one-time payments from the hotel he owns with Ruffin.

Behind the campaign’s fundraising disarray lay a personal financial storm.

Trump’s tax records reveal that when he decided to leverage his brand in the political arena, its true bottom line bore little resemblance to the gold-plated success story he was hawking to the American people.

Most of his core businesses were losing money. The deep draughts of cash from “The Apprentice” and the resulting fame that had sustained him for a decade were steadily running dry.

It did not help when NBC, which aired Miss Universe and “The Apprentice,” cut ties with him after he announced his candidacy in 2015 with racist comments about immigrants. Nor did it help when Deutsche Bank turned down his request for a loan for work at Turnberry, the Scottish golf resort that he had bought for roughly $60 million in 2014 and that was on its way to gobbling up almost $80 million more by the end of 2016, according to tax return information. By year’s end, he would agree to pay $25 million to settle a class-action lawsuit involving allegations that Trump University was a fraud.

Whether for his businesses, his campaign or both, Trump was furiously moving money, his tax records show.

Since 2012, he had drained a lot of the cash he had on hand. That year, he took out a $100 million mortgage on the commercial space in Trump Tower and received nearly the entire amount as a cash payout. The following year, he took $95.8 million out of a real estate partnership account at Vornado Realty Trust. After selling $38.6 million in stock in the first months of 2016, he ended the year having sold nearly $30 million more.

And there was another manoeuvre, the one that experts consulted by the Times described as highly unusual: the more than $21 million in one-time payments that the Trump-Ruffin joint venture paid out in 2016.

By analysing the tax return information and public records, the Times was able to trace the flow of money — first to companies that Trump alone controls and from there to Trump himself.

It was created in 2004 as Trump and Ruffin were drawing up plans for the Trump International Hotel. Precisely what it did, though, is obscure. It had no employees, or at least no payroll. And while the Trump-Ruffin joint venture certainly spent several million dollars a year to promote its room rentals and condominium sales, that money did not go to Trump Las Vegas Sales and Marketing. The company’s tax records show that it had little income over the years, posting modest profits only twice: $54,924 in 2007 and $420,756 in 2008.

Then, in 2016, came a payment of $13,756,623.

Trump disclosed the payment in his 2017 federal ethics filings, but only with the tax records is it possible to see the entire chain of transactions. On the ethics filing, he said Trump Las Vegas Sales and Marketing had a “deal” with a subsidiary of the joint venture, but no other details are given.

The second unusual payment was for $2,685,000, divided between the two companies that hold Trump’s share of the hotel and then paid out directly to him. He called it one thing for the IRS (a “loan fee”) and another in his public filings (a “sponsor fee”).

The Trump-Ruffin hotel company listed one other large one-time expense on its 2016 tax return: a $4.8 million “development fee.” While the Times was unable to trace the path of all of this money through Trump’s tax records, his public disclosures say that a company called Trump Las Vegas Development also had a deal to receive development fees from a subsidiary of the joint venture. (That company, according to the filings, actually had revenue of $8.2 million from January 2016 to April 2017. It is not clear where the additional $3.4 million came from.)

The IRS lets companies use business expenses like sales and marketing payments to reduce taxable income — but only if they are “both ordinary and necessary.” The Trump-Ruffin hotel venture wrote off at least $21 million in one-time payments to Trump.

The tax records do not specify when the payments were made or where the joint venture got the money for them.

But taken together with public records, they may offer some clues.

The Las Vegas hotel had long been a money loser. Between 2010 and 2012, each partner put $23 million into the business. Its losses were narrowing, though, and it began 2016 with $6.3 million in cash reserves.

That might have been a decent cushion, but it was hardly enough to cover the more than $21 million in payments to Trump. In fact, the payments drove the hotel to its biggest loss ever.

Then, seven weeks before the election, something else unusual happened. The Trump-Ruffin partnership borrowed $30 million from City National Bank in Los Angeles. Trump signed the loan documents in New York City, but tax records show that Ruffin personally guaranteed nearly the entire amount, should the company ever be unable to pay.

The partnership was not required to disclose on its tax returns how the borrowed money would be spent. But the timing of the loan, combined with the partnership’s lack of available cash that year, strongly suggests that the loan funded the millions of dollars in payments to Trump.

Finally, a Train

After being lobbied for years, the Trump administration did what Obama’s wouldn’t.

The dream shimmered at the edge of vision in the desert heat.

Ever since Amtrak had shut down the last train in 1997 — the Desert Wind, which wound its way north from Los Angeles — Ruffin and the other moguls who control the Las Vegas Strip had planned, waited, hoped.

Train schemes had risen and, inevitably, fallen — among them a proposal for a maglev train levitated and propelled by magnets. But in 2009, with the support of Harry Reid, the Nevada Democrat who was then Senate majority leader, the federal government had taken a crucial step, approving a rail corridor between Las Vegas and Victorville, in the California high desert.

Four years later, a proposed $5.5 billion federal loan for a bullet train had come before the Obama Transportation Department, to furious opposition from two powerful Republican lawmakers — Paul Ryan, who was chairman of the House Budget Committee, and Jeff Sessions, then the ranking member of the Senate Budget Committee — who considered it an untenable taxpayer risk. Ultimately the loan had been rejected, in part because the project could not comply with buy-American rules.

It was after Trump’s inauguration that Ruffin mentioned the predicament of his neighbour Anthony Marnell II. Marnell is an architect and oversaw the building of casinos like the Mirage, the Bellagio and Wynn Las Vegas. He also controlled the company trying to build the high-speed train.

So, a friendly favour for a friend.

“I mentioned it to Donald. And that would be something below his pay grade, so it would have to go to the Labor Department or the Transportation Department,” Ruffin told Forbes. “He said it sounds like a good deal, especially if it employs 80,000 people.”

Not long after, Marnell told the Review-Journal that he was considering approaching the Trump administration about a federal loan like the one the Obama administration had rejected. Las Vegas needed the train more than ever, he argued, now that the Oakland Raiders football team was moving to town.

Marnell’s long-sought federal loan remained elusive, and in the fall of 2018, he sold the business, renamed XpressWest, to a company owned by Fortress Investment Group LLC, a big New York financial firm. (Marnell, who declined to comment for this article, kept an equity stake in XpressWest.) Fortress owns a company named Brightline, which operates a private rail service in Florida. Ben Porritt, senior vice president for corporate affairs at Brightline, said its trains had previously received several allocations of federal tax-exempt bonds.

These bonds, earning interest free of taxes, help companies attract private investors to often higher-risk projects. While they are distinct from the kind of federal loan Marnell sought, they nonetheless require government approval.

In March of this year, the Transportation Department’s Credit Council approved the sale of $1 billion in tax-free bonds, the final tranche of a $15 billion program begun during the Obama years. The credit panel, made up of heads of the agency’s various branches, is led by Steven Bradbury, the department’s general counsel and acting deputy secretary, who came under fire during his confirmation for his role in providing legal sanction for torture techniques during the George W Bush administration. Overseeing the panel is Trump’s transportation secretary, Elaine Chao.

Officials in California and Nevada were watching. Less than a year earlier, Trump, feuding with California’s liberal leadership, had pulled federal funds for a separate high-speed rail project there. Now, with federal approval assured, California and Nevada voted to allow the issuing of an additional $3.2 billion in bonds.

The train company says it hopes to start construction later this year. For now, the route will start in Victorville, 90 miles from Los Angeles, though there are plans to extend it considerably closer, to Rancho Cucamonga. One day, the company hopes, it will run all the way to Los Angeles.

The Las Vegas terminal will be on the Strip, a short bus ride from the Trump International Hotel.

“We would benefit some,” Ruffin told Forbes. “But there are a lot of hotel rooms here. A lot of places they can go.”

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