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In 2016, Donald Trump’s campaign ran on a shoestring, and won. He planned a different 2020: It would be the biggest, richest, most expensive presidential campaign ever. But with just two months to go before the election, the president has burned through massive amounts of money, and now his campaign is at a cash disadvantage to the Democratic nominee, Joe Biden.

This is an amazing feat—how did the campaign blow through nearly $1 billion to so little effect?—yet also inevitable. The Trump 2020 campaign seems to be running on the same principle as many of the president’s commercial endeavors: Trump gets richer, while other people’s money gets lit on fire. This was how some of the president’s real-estate ventures and casinos operated, and so it’s unsurprising that it’s how he’s chosen to run his campaign—and the country.

Few things get Trump peeved faster than bringing up the four times his companies declared bankruptcy. Chris Wallace of Fox News learned this in 2015, when, during a GOP primary debate, he asked Trump whether voters should trust him to run the government, given his private track record.

“I have never gone bankrupt, by the way. I have never,” Trump snapped—he’d merely used the nation’s bankruptcy laws to his advantage.

“At the same time, financial experts involved in those bankruptcies say that lenders to your companies lost billions of dollars,” Wallace replied. “With that record, why should we trust you to run the nation’s business?”

“I have used the laws of this country just like the greatest people that you read about every day in business have used the laws of this country, the chapter laws, to do a great job for my company, for myself, for my employees, for my family, et cetera,” he said.

Trump was right. He and his family have made out well, but at the expense of others. Each time a company declares bankruptcy, it sheds debt—in other words, someone who it owes money loses some or all of their stake.

Start with the first bankruptcy, in 1991. When Trump built the Trump Taj Mahal in Atlantic City, he bragged he didn’t have to use then-hot junk bonds to finance the project. He was lying. He did use junk bonds, and within three years he’d fallen behind on interest payments, even in a business famous for always earning cash. When he declared bankruptcy, he was forced to sell off some treasured assets—his yacht, his airline—but he owed the banks so much that they opted to work with him rather than take everything. In other words: They took a big loss. The following year, another casino, the Trump Plaza, failed. This time, Trump lost his stake and control of the company, but kept his CEO title.

By the mid-1990s, Trump was toxic enough that practically no bank would lend him money, figuring there was a good chance they’d end up losing it. One exception was Deutsche Bank, which, as The New York Times Magazine put it, had developed a reputation “as a reckless institution willing to do business with clients nobody else would touch.” But in 2008, amid the financial collapse, Trump couldn’t make debt payments, and turned around and sued Deutsche Bank to forestall it from collecting. (Why Deutsche Bank continues to loan Trump money is an intriguing question.)

Trump also sought alternative ways of financing projects. For example, Trump turned to Russian investors as a new source of cash. (You know how that story ends.) He also simply issued bonds to the public, trading on his name, which may have been tarnished on Wall Street but had been burnished by his TV show and other projects. In 2009, when the Trump Organization again declared bankruptcy, these small investors took the hit.

“People knew who Donald Trump was and for that reason were willing to trust the bonds, and they got burned,” the bankruptcy expert Lynn LoPucki told ABC in 2011. “The people who invested with him or based on his name lost money, but he himself came out pretty well.”

At the same time, Trump was also leveraging his celebrity for other projects. He licensed his name to several developments at the height of the real-estate bubble, attracting buyers who (erroneously) viewed his name as a gold standard. When the projects failed, it became clear that Trump had no personal stake, having simply taken a fee for the use of his name.

The Trump campaign seems to have a great deal in common with these earlier business ventures. This is not just a matter of poor results, though the campaign does seem shaky. At the moment, Biden has a consistent, though not commanding, lead in the polls, and has for months. In several key states he won in 2016, Trump trails Biden. In July, the president sacked his campaign manager, Brad Parscale.

Trump’s 2020 campaign was always going to be challenging—it’s hard to persuade voters to reelect a president of whom most of them disapprove. But he had the advantage of incumbency (only two presidents since World War II have not been reelected) and a huge money machine.

Now that machine seems to be sputtering a bit. The New York Times reports that the Trump campaign is in a cash crunch. This matches up with circumstantial evidence, such as Trump pulling much of his television advertising, even as Biden widely outspends him. From January 2019 to July 2020, Trump raised $1.1 billion, but has already spent $800 million. The Biden campaign and the Democratic Party raised a combined $364 million in August—setting a record—but Trump has still not reported August numbers.

Trump could still win the election, and perhaps all will be forgotten. Even if he does, though, the campaign has been a colossal, profligate use of money. Figuring out why the campaign is in tough straits now is difficult, especially without the latest filing available. Perhaps the campaign banked on getting more big-dollar donors. Perhaps it isn’t getting the small-dollar return it heavily invested in, or perhaps the price tag has just proved too dear. As my colleagues Ian Bogost and Alexis C. Madrigal explained in April, “People have marveled that Trump never stopped running Facebook-ad campaigns. And the reason is, he couldn’t. The whole point is that the campaign has to keep fresh data flowing through the system.”

In any case, the campaign has also spent millions and millions of dollars on things that clearly benefit Trump, his family, and his company, but do not so clearly aid the cause of electing Republicans to office.

As Eric Lipton reports in The New York Times, Trump has spent nearly $60 million of campaign money on legal bills. Candidates need good lawyering, of course, but this number far outstrips other campaigns’ tabs because the president has drawn on political fundraising to foot the bill for his litigiousness, to pay attorneys to represent him in investigations by House Democrats and Special Counsel Robert Mueller, and to pay for the defense of aides who have been swept into legal inquiries in his various scandals.

There are also multiple former aides who have been hired by the Trump campaign or the Republican National Committee after leaving the White House. Omarosa Manigault Newman claims that when she left the administration, she was offered a $15,000-a-month no-show job to keep her happy and quiet. She is not the most reliable source, but other former White House aides have taken a similar path, including a former bodyguard, Keith Schiller, and a body man, John McEntee, who was fired amid a fraud investigation but, because irony is dead, has since returned as head of personnel for the White House.

Some costs come from sops to the president’s fragile ego. The campaign has spent more than $1 million on ads in the District of Columbia so that Trump will see them, even though neither D.C. nor Virginia nor Maryland is likely competitive in November. It also shelled out $11 million for Super Bowl ads in order to go toe-to-toe with Michael Bloomberg. The campaign also spent more than $100,000 on magnetic pouches for cellphones, to keep fundraiser attendees from recording and leaking the president’s private remarks. This may spare the president some embarrassment—though he’d probably get more benefit from a magnetic pouch around his own phone, keeping him from his Twitter account—but it’s a dubious use of campaign resources.

Even more questionable is the cash that the Trump campaign has not just wasted, but has directed to Trump. Forbes reported that the campaign had paid $2.3 million of donor money to the Trump Organization for things like food, lodging, and rent. That includes $380,000 in just two days in March. The RNC has spent more than $17 million at Trump properties since 2016.

That’s a nice surge of revenue for the president from his own campaign—or rather, from his donors—and one enabled by the fact that, unlike other presidents, he did not divest from his business interests upon taking office. Trump could waive a fee for these costs, or offer discounts; he’s the only one legally allowed to make that sort of in-kind donation. But he has not.

In fact, as of August, he hadn’t given a dime to his reelection effort. Bloomberg reports that Trump is now considering a $100 million gift to his campaign, which would be unprecedented. Believe it when you see the Federal Election Commission reports. That would put Trump in the red for the campaign, when it appears he’d rather line his pockets with the hard-earned cash of supporters who presumably expect he’s using it to get reelected president. If his track record is any guide, revenue for Trump is the whole point. When Parscale was fired, one reported reason was that Trump was upset that he was making a neat profit on the campaign. Only Trump is allowed to do that.

At this point, a cynical reader—especially one who opposes the president—might say: Who cares? The people who are being exploited have willingly given to Trump, and they ought to know by now how he operates. This is true, to a point. But such bad-faith use of donor dollars is a problem because it creates cynicism about the election system, and because it further tips the balance of political power toward large donors, who can afford to give more.

More important, this profiteering is how Trump has run the country as well. The economy is in shambles; the unemployment rate is high, and signs of more danger are on the horizon. The stock market, a rare bright spot, has taken a beating recently. The federal deficit is at record levels—in part because of much-needed COVID-related spending, though Trump had driven it up, including with tax cuts for wealthy people like himself, even when the economy was good.

But Trump is doing okay. In addition to the RNC and campaign spending coming his way, there’s also the business at hotels like the Trump International in Washington, which has become a magnet for foreign officials seeking to curry favor. There are also the charges to the federal government to use his facilities when he visits them, which are frequent. The Washington Post calculates that the government has paid Trump more than $900,000, including charges like room rates of $650 a night for Secret Service agents.

Trump likes to boast that he donates his presidential paycheck, but don’t worry—if you pay taxes in the U.S., you’re still paying him. It’s like he told Chris Wallace in 2015: He’s doing a great job for his company, himself, his employees, and his family. For campaign donors and taxpayers? Not everyone can win.

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