What Are the Chances Trump Could Actually Go to Jail?

New York state legal experts—and one of the president’s biographers—weigh in.

Will America soon have its first Shawshank President? Will Donald Trump find himself fending off riots in the Attica mess hall? Tweetless and at the mercy of 2,000 “angry Democrat” inmates?

A number of recent developments show that one cannot rule it out. Things took a decidedly serious turn last week when New York prosecutors told a federal judge that there were “public reports of possibly extensive and protracted criminal conduct at the Trump Organization.” They added that they that they may also be investigating possible crimes involving bank and insurance fraud, according to the New York Times, which also reported that Deutsche Bank has been complying with a Manhattan District Attorney’s Office subpoena for months, turning over detailed financial records in connection with some $2 billion the bank has lent Trump.

The news comes on the heels of a Supreme Court ruling last month that declared the president was not immune from state criminal investigations, therefore clearing the way for a New York grand jury to subpoena Trump’s financial records, an effort spearheaded by Manhattan District Attorney Cyrus R. Vance Jr.

For Trump, the stakes couldn’t be higher once he leaves office: He could go from the White House to the Big House.

So, I asked some experts the likelihood that the president could really wind up in a New York prison. “Absolutely yes, if we are a nation of equal justice and Trump is convicted of serious felonies,” Trump biographer David Cay Johnston told me. But he quickly added, “Whether it happens is entirely unpredictable.”

Still, New York has a real chance at putting Trump behind bars. The state has jurisdiction over most of his properties and operations relating to his 2016 presidential campaign. Crucially, states also are not subject the U.S. Department of Justice’s rule that a sitting president may not be prosecuted for federal crimes. Trump, therefore, is stripped of his four-year kryptonite shield if he is re-elected. A state indictment of a sitting president, though historically unprecedented, is entirely possible. His DOJ-Roy Cohn, Bill Barr, is constitutionally powerless to intervene.

That should make Trump uneasy, especially as New York Attorney General Letitia James ramps up her own investigations. “We will use every area of the law to investigate President Trump and his business transactions and that of his family,” she declared after taking office two years ago.

At the same time, Vance’s subpoena appears to go beyond obtaining financial records relating to alleged pre-election hush money payments to silence two women, Stormy Daniels and Karen McDougal. Both of the women claim to have had affairs with Trump. Information gleaned from the DA’s inquiry could expose tax cheating and money laundering as well as bank and insurance fraud, which are felonies.

Johnston told me he’s confident that Vance already has Trump’s New York tax filings. Even though the IRS and state tax authorities share tax information on citizens and business entities, it’s unclear whether he also has the president’s federal returns. The DA is seeking Trump’s financial records from his accounting firm Mazars USA in addition to Deutsche Bank—to compare that data with what he already possesses, looking for corroborating information, according to Johnston.

“Trump has a well-documented history as a tax cheat and for hiding business records,” Johnston said. “This is garden variety tax fraud, a straight-up tax scam that could easily be a felony.”

That doesn’t necessarily mean he will go to jail. More often than not, tax cheats get away with heavy fines in lieu of prison sentences, Johnston said. Moreover, Trump, like many very wealthy people, will continue to throw monkey wrenches into the judicial system with appeal after appeal and other rope-a-dope tactics until revenue agencies finally become open to a low-punitive settlement.

This is echoed by Duncan Levin, formerly a senior staff member under District Attorney Vance and an ex-assistant U.S. attorney. Whether the president would actually be sentenced to prison is a political call, Levin said. “Can you imagine an ex-U.S. president actually being sent to prison?” he told me. “It’s inconceivable that Trump didn’t know about the hush money payments. But it’s highly unlikely that he’d be arrested on misdemeanor charges. They would have to be very serious felonies.” False statements to financial institutions would count.

More likely, he added, the DA may be zeroing in at this point on Trump’s inner circle. “Michael Cohen didn’t act alone. He collaborated with people within the Trump organization to cover up the hush payments just before the election,” Levin said. Look, at least initially, for indictments of Trump underlings.

The good news, though, is that Vance will not put off his investigation and possible indictments until after the November election. DA’s proceed on cases irrespective of extraneous events, including a general election, Levin said.

But the hope of many that Trump could finally be held accountable for his crimes may be remote. At most, one can imagine him behind bars at a white-collar correctional facility like that of his former lawyer Michael Cohen, as opposed to hard time at a penitentiary like Attica. For now, though, time will tell. The Americans who want to see justice carried out are more likely to watch this shamed crook-in-chief spending his remaining years out of office consumed in exhausting and financially draining legal battles, fully exposed for the criminal he’s always been.

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James Bruno

James Bruno is a Washington Monthly contributing writer and former U.S. diplomat. Read his blog, DIPLO DENIZEN, and follow him on Twitter @JamesLBruno. The opinions and characterizations in this article are those of the author, and do not necessarily represent official positions of the U.S. government.