O'Brien: Why Trump fears leaving the White House

Photo by Doug Mills of The New York Times / President Donald Trump speaks during an election night event in the East Room of the White House in Washington, early Wednesday morning, Nov. 4, 2020.
Photo by Doug Mills of The New York Times / President Donald Trump speaks during an election night event in the East Room of the White House in Washington, early Wednesday morning, Nov. 4, 2020.

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. 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. And his 2016 ascent to the White House opened his eyes to the presidency's legal armor - which he interpreted broadly and often inaccurately.

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. He 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. Much of what Trump holds isn't liquid, meaning he may be hard-pressed to sell assets quickly if he needs to raise funds.

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 (Cyrus Vance) is investigating Trump for possible tax fraud and falsification of business records, according to appellate court filings.

New York Attorney General Letitia James has launched another investigation, also focused on whether the Trump Organization and the Trump family manipulated valuations to secure funding or engineer tax benefits. James's probe is a civil case, which could bring hefty financial penalties against Trump but no prison time. Vance's investigation is a criminal matter, however, and if the Trump crew is found guilty of felonies, prison time is on the table.

Trump's team has fought back hard against the Vance investigation, including arguing before the U.S. Supreme Court that a sitting president is immune from state criminal prosecutions. While the court rejected that notion in a landmark ruling over the summer, it would become a moot argument in any venue once Trump is no longer president.

It's unclear how aggressive law enforcement officials in the Biden administration will be toward Trump. They could resurrect some of the obstruction charges that have gone fallow since former Special Counsel Robert Mueller ended his probe. On the other hand, the political firestorm that could ignite might persuade Biden to hold back.

What's clear is that Trump's money and freedom are in play. As he comes to grips with losing the 2020 election, he will continue responding ferociously and unpredictably, like a man who for 74 years has been accustomed to getting away with almost anything.

Bloomberg News

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