It isn't a new idea that President Trump is better at playing a billionaire on TV than earning enough money to be one in real life. But The New York Times got the goods to prove it — 18 years worth of tax documents, from 2000 to 2018 — and released the first bombshell Sunday night (while promising to "publish additional articles about our findings" in coming weeks). It's a doozy.One eye-catching takeaway from the deep look into Trump's strenuously shielded tax filings is that Trump loses a lot of money. Like, a lot. He loses millions at his prized foreign and U.S. golf properties, the Trump International Hotel in Washington, D.C., and many of the roughly 500 entities that make up the Trump Organization.The Times also details how Trump uses those deep-red losses to avoid paying federal income tax, at least in the U.S. There was a two-year period in which he made too much money to avoid paying taxes, thanks to his share in NBC's The Apprentice, but he then filed for a refund when the opportunity presented itself after the 2008 financial meltdown. That $72.9 million in refunded taxes plus interest is under audit and has been for years, the Times reports. Trump paid just $750 in federal income tax in both 2016 and 2017, the most recent years in the data the Times obtained.But "the picture that perhaps emerges most starkly from the mountain of figures and tax schedules prepared by Mr. Trump's accountants is of a businessman-president in a tightening financial vise," deep in debt with the bill coming due, the Times reports. That raises the troubling question of whether Trump can literally afford to lose power on Nov. 3 — and what he might do to prevent an electoral defeat and financial ruin.During the 2016 campaign, Trump proclaimed himself the "King of Debt," telling CBS's Norah O'Donnell that "nobody knows debt better than me. ... I've made a fortune by using debt, and if things don't work out I renegotiate the debt. I mean, that's a smart thing, not a stupid thing." Renegotiating means "you go back and you say, 'Hey, guess what, the economy crashed,'" he explained. "'I'm going to give you back half.'" That nearly destroyed him in the early 1990s, after almost all his bets failed in short order.The lessons Trump learned in the early 1990s "undoubtedly shaped his business approach and the conservative nature of how we conduct business today," Eric Trump, who currently runs the Trump Organization for his father, told The Washington Post in 2018. Trump started paying cash for properties in about 2006, when his Apprentice money started coming in.But the newly obtained "tax records show that Mr. Trump has once again done what he says he regrets, looking back on his early 1990s meltdown: personally guaranteed hundreds of millions of dollars in loans, a decision that led his lenders to threaten to force him into personal bankruptcy," the Times reported Sunday. "This time around, he is personally responsible for loans and other debts totaling $421 million, with most of it coming due within four years. Should he win re-election, his lenders could be placed in the unprecedented position of weighing whether to foreclose on a sitting president."Along with more than $300 million in loans coming due in the next four years for which he is personally responsible, Trump might have to pay back the federal government more than $100 million, including interest and penalties, if the Internal Revenue Service determines he improperly obtained the $72.9 million tax rebate. Trump has valuable assets he might be able to sell (but really doesn't want to) — but he also currently serves as the top executive of the same federal government that includes the IRS and America's federal prosecutors.If you think Trump wouldn't lean heavily on Attorney General William Barr or Treasury Secretary Steven Mnuchin to protect his personal finances in a second term, or that Barr or Mnuchin are above tipping the scales even a bit, Trump might have a bridge to sell you. Or a condo. Mnuchin's refusal to hand Trump's tax returns over to congressional investigators, and the Justice Department's half-successful defense of that decision, are the reason we are learning what's in Trump's tax filings from The New York Times.Deutsche Bank, one of Trump's largest lenders, would likely "do the easy thing" and extend Trump a short-term loan extension until he's out of office, Mike Offit, one of Trump's bankers in the 1990s, told Mother Jones in August. "It's even more trouble if they try to foreclose on the president. Good luck with that. That's the way they're going to put themselves back in the news every day."Any other bank would decide that Trump "is toxic," U.C. Berkeley real estate finance professor Nancy Wallace told Mother Jones. "Exposing yourself to that kind of oversight under the current regulatory reality, for lenders who are large enough to provide capital to him, is just a nonstarter." That would leave Trump at the mercy of "opportunistic lenders" less hesitant to come after him for delinquency, even in the Oval Office, Offit said. Hedge funds "would lend to Ted Bundy. They don't care." Wallace agreed that some private equity fund could "be very tempted if he was willing to pay a very high coupon."The Times, working from Trump's self-reported tax information, could not determine his net worth or the identity of his lenders. Having a president deeply indebted to unknown lenders is a clear national security threat.Which brings us to our second question: If Trump can't afford to lose power, can America afford having him in power for another four years?The available data just scratch the surface of "the actual and potential conflicts of interest created by Mr. Trump's refusal to divest himself of his business interests while in the White House," the Times reports. "His properties have become bazaars for collecting money directly from lobbyists, foreign officials, and others seeking face time, access, or favor." Turkey's authoritarian government, led by President Recep Tayyip Erdogan, has "not hesitated to leverage various Trump enterprises to their advantage," the Times says.On issue after issue, how can we know if Trump is acting in America's interest or his own?"It's highly disconcerting," Virginia Canter, chief ethics counsel at the watchdog group Citizens for Responsibility and Ethics in Washington (CREW), told Mother Jones. "I'm sure in some ways the best thing that could happen is that he not win re-election."Want more essential commentary and analysis like this delivered straight to your inbox? 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