Trump's Election Loss Leaves Him Vulnerable to Financial and Legal Danger

Donald Trump is the luckiest man alive. Unlike almost, well, everyone, he’s been protected from the consequences of his own mistakes his entire life.

Born into a wealthy family, he was insulated from lukewarm academic prospects and serial business crack-ups by his father’s money. (“I often say that I’m a member of the lucky sperm club,” is how he put it in one of his books.) Emerging as a reality-TV star in the early 2000s, Trump discovered that fame allowed him to be as predatory as he pleased without repercussions. (“When you’re a star, they let you do it.”) And his 2016 ascent to the White House opened his eyes to the presidency’s legal armor — which he interpreted broadly and often inaccurately. (“I have an Article II, where I have the right to do whatever I want as president.”)

Although Trump has over the years juggled, among other difficulties, ho-hum grades, the threat of personal bankruptcy, sexual assault accusations, an intensive federal investigation and an impeachment, he has plowed ahead relatively unwounded and unencumbered by regret. Wealth, celebrity and the presidency have kept him buoyant. All that insulation has also meant that he hasn’t learned from his mistakes. Every personal and public reckoning has been postponed or shunted aside.

Now, however, Trump is staring at two threats that loom after he leaves the White House in January. One is financial, the other legal. Neither is entirely under his control. And both may help explain, along with his perennial inability to accept losing, why Trump won’t acknowledge that President-elect Joe Biden is going to succeed him and why he has enlisted the Republican Party to help him gaslight Americans about the outcome of the presidential election.

Trump and the patchwork of businesses he houses inside the Trump Organization are saddled with more than $1 billion in debt, which Dan Alexander of Forbes has helpfully tallied. A portion of that total has been divulged over the past few years in the president’s personal financial disclosures, on file with the Office of Government Ethics. The New York Times recently revealed that Trump has personally guaranteed at least $421 million of the debt, with more than $300 million coming due within four years.

In other words, Trump is on the hook for a lot of money that he may have to scramble to repay in a Covid-19-battered economy in which his industries — hotels, leisure, urban real estate — have been particularly pummeled. Forbes estimates his assets are worth $3.7 billion; Bloomberg News pegs them at about $3.2 billion. He’s not going broke. But if the economy continues to struggle in coming months, those valuations will be tested. And much of what Trump holds isn’t liquid, meaning he may be hard-pressed to sell assets quickly if he needs to raise funds. Among Trump’s most valuable holdings, for example, are minority stakes in two properties controlled by Vornado Realty Trust. Rumors of fire sales might further depress the value of his portfolio.

Another thing that would weaken Trump’s ability to negotiate sweetheart financial deals or forgiveness: leaving the presidency.

On the legal side of the ledger, Trump, his children and their company face aggressive investigations into their finances, accounting practices and tax payments.

The Manhattan District Attorney’s Office is investigating Trump for possible tax fraud and falsification of business records, according to appellate court filings. In this probe, which is also examining the president’s payment of hush money to two women who allegedly had sexual encounters with him, the DA’s office is seeking eight years of Trump’s tax returns. It is also taking a look at whether Trump inflated the value of his properties and other assets in order to secure funds from lenders and investors.

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