New top story from Time: For Donald Trump, There’s More at Stake on Election Day Than Just His Political Future

For three and a half years, donors, lobbying groups, foreign governments and even the Secret Service have racked up large bills at properties owned by President Donald Trump. Because Trump bucked tradition and declined to put his assets into a blind trust, the lines between his presidential prerogatives and his personal interests were blurred, and over time everyone got used to potential conflicts of interest that in any other recent presidency would have been scandalous.

But Trump’s lack of financial transparency took on a more urgent quality after the revelation Sunday that he has hundreds of millions of dollars in debt coming due in the next four years, according to reporting from the New York Times. Forbes estimated that Trump controls about $3.66 billion in assets and holds a total of about $1.13 billion in debt. He also faces an ongoing Internal Revenue Service audit, and faces potential legal fallout from New York state investigations into his business dealings.

All of which means Trump has a lot more riding on the outcome of the Nov. 3 election than whether or not he spends the next four years at the apex of American political power. He faces multiple, costly legal battles. He is potentially on the hook for millions of dollars in tax penalties and interest. And perhaps most critically, he owes hundreds of millions of dollars and is saddled with loss-making properties that are digging him deeper in the hole. In short, losing the White House could be very costly for Trump.

“Trump may be the first president who is fearful of leaving the office because he may do worse financially when he leaves,” says Timothy Naftali, a presidential historian at New York University. Harry Truman famously lived on a military pension that was a fraction of his White House pay after choosing not to monetize his time in office, but most recent ex-presidents have done better financially, signing book deals and taking large speaking fees. Trump is the “first president to monetize the presidency while he’s actually in the Oval Office,” Naftali says.

For a time, there was at least some benefit to Trump in his money-losing endeavors, the Times reports: write-offs that reduced to zero his annual income tax bill for many years. Trump dismissed the allegations about his low tax payments during a press conference Sunday evening, calling the reports “totally fake news.” Trump, who says he’s donated nearly all of his presidential salary to government agencies since taking office, said his returns are still under audit, and took aim at the Internal Revenue Service, which technically he oversees. “The IRS does not treat me well,” Trump said, “They treat me very badly.”

Ironically, Trump’s tax avoidance measures may now increase the chances he has to return to the private sector and face the financial music. Democrats pounced on the report about Trump’s low tax bills, trying gin up outrage among working voters who see large chunks of their income going to the Treasury. The Biden campaign started selling T-shirts that read, “I paid more income taxes than Donald Trump.”

“Even for a wealthy person, paying no taxes in most years and claiming these losses, it’s just not normal,” says Seth Hanlon, who worked on tax policy in the Obama White House and is a senior fellow at the left-leaning Center for American Progress. Massachusetts Congressman Richie Neal, the Democrat in charge of the House Ways and Means Committee, raised the alarm that Trump may try to influence the outcome of the audit. “Donald Trump is the boss of the agency he considers an adversary,” Neal said in a statement. Neal’s committee is suing Trump to get access to his tax returns.

Trump is trailing former Vice President Joe Biden in national polls, but it’s unclear if the new revelations will sway voters on the fence about Trump. Trump has always been seen by voters through the lens of a celebrity, says Lauren Wright, a political scientist at Princeton University, which means “he’s evaluated with a different ethical yardstick than a traditional politician.”

The news of Trump paying little in taxes could be detrimental among some independents who are just tuning into the presidential race, Wright says, but it is unlikely to have a bigger impact. “For a traditional politician, a lot of what Trump has been through would have been a disaster” such as the Access Hollywood tape of him sexual assaulting women, the Robert Mueller investigation into his campaign’s ties to Russia, and his impeachment and acquittal. “These types of things do not seem to affect him,” Wright says.