The short answer to this question is: Nobody knows! Not all the prosecutors who are planning to seek indictments against him, not the political insiders, not the Justices of the Supreme Court – and not even Donald Trump himself really has a clue.
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But maybe we can get some sense of the likelihood that ex-President Trump will be going to prison. We can do that by answering a series of questions, the first of which is: Will Trump be pardoned?
Will Trump Be Pardoned?
Before noon on January 20th, there are two people who could conceivably pardon Trump of any federal crimes he might have committed – Mike Pence, or Donald Trump himself. After making a deal with Pence, Trump could resign and Pence would become President. Pence would then pardon Trump. That would be perfectly legal, and Trump could not be prosecuted for any federal crimes he committed before he took office or while he held office.
Trump could also temporarily step aside – perhaps for just an hour or so – allowing Pence to step in as Acting President. He would issue the pardon, and then Trump would reassume the presidency until January 20th.
A third alternative would be for Trump to pardon himself of all federal crimes. It is unclear if that pardon would be legal, and it would surely be contested immediately.
Once Trump has left office, Joe Biden, or a future president could issue a pardon. Biden, however, has already said that he would not pardon his predecessor, whom he clearly detests.
Interestingly, one of the more beneficent traits shared by Trump and Biden is their devotion to their children. In the cases of both fathers, this devotion has led to very valid accusations of nepotism. In fact, perhaps the main reason Biden may not issue a pardon to Trump is because of his relentless investigations of Hunter Biden’s suspicious foreign business pursuits.
Investigating Family Businesses
Turnabout is surely fair game. If President Donald Trump could go after the business dealings of Hunter Biden, Joe Biden’s son, then surely prosecutors could investigate the business dealings of Trump’s three oldest children – Donald Junior, Eric, and Ivanka – and perhaps for good measure, Ivanka’s husband, Jared Kushner. In fact, just the threat of subjecting them to prosecution could be used as leverage in legal proceedings against ex-President Trump in either federal or state court. For that reason, alone, it would be inexplicable if Trump does not pardon this foursome before leaving office.
In one instance --which involved not just income tax evasion, but also blatant nepotism -- Ivanka Trump, who happens to be one of the leaders of the Trump Organization, received a “consulting fee” of $750,000 from the organization which she herself, helps run. Surely, she and her dad were aware of this blatantly illegal tax write-off.
One can only imagine what other illegal activities carried out at the family business by these three Trump children will be uncovered by New York State and federal investigators. And so, even with immunity from federal prosecution, the president’s offspring’s business dealings may place the ex-president in serious legal peril. So, it would appear to be a no-brainer for Trump is issue pardons for his children and son-in-law before leaving office.
Still, a self-pardon, or one issued by Pence, would, in effect, be a tacit admission of guilt. So, it’s conceivable that Trump’s vast ego might tempt him to ignore the advice of all his lawyers, forgo a pardon and proceed to defend his honor in the federal courts. If nothing else, this would enable him to continue to occupy his place at the front and center of our nation’s political stage.
And then too, undergoing a federal prosecution would not only fuel the ex-president’s infinite ability to indulge in personal grievance, but further inflame his legions of followers who believe his claim that the election was stolen from him.
But If Trump does get pardoned, that will greatly reduce the odds that he will go to prison since it will absolve him of punishment for any federal crimes he may have committed. But that still leaves him in great legal jeopardy of being prosecuted for the commission of very serious state crimes.
Trump's Possible Federal Crimes
If Trump is pardoned, then it will be only for any federal crimes he may have committed – such as evasion of paying federal income tax. He may well be forced to pay more than one hundred million dollars in evaded taxes, but a presidential pardon would spare his serving time in prison.
You may recall the name of one of the most infamous criminals in American history – Al Capone. He managed to dodge the most serious criminal charges – including murder. But he ultimately served a life prison sentence for federal income tax evasion. He had neglected to pay income tax on the income he derived from committing crimes.
The only major party presidential candidate since Richard Nixon to refuse to make his income tax returns public, Donald Trump legally sheltered his from public scrutiny during his term in office. But after January 20th, they will not only be turned over to prosecutors in New York State, but also made available to the public so that we can finally see what he had been hiding.
We already know that over the fifteen-year period from 2001 through 2015, Trump paid federal income tax in just five of those years. He averted paying any taxes during the other ten years because of very large business losses. In addition, during the next two years, he paid just $750 annually in personal income tax. Given the vast losses he claims to have sustained, it defies credulity that the man has not yet had to once again declare personal bankruptcy – let alone maintain his status as a billionaire.
Avoiding Income Taxes
If Trump did cheat on his federal income taxes, then he surely cheated on his New York State income taxes as well, since the IRS and the state tax department share their tax returns. While a federal pardon would shield him from federal prosecution, he could still be prosecuted by New York. Unless, of course, he also secured a pardon from New York Governor Andrew Cuomo. What are the odds that that would ever happen?
Let’s now consider a second very serious federal crime that Trump has very possibly committed – acceptance of an illegal campaign contribution from his personal lawyer, Michael Cohen. There was a $2,700 ceiling on individual contributions to presidential candidates in 2016, but Cohen was found guilty of having hidden a $130,000 contribution to Trump’s 2016 campaign, and was sentenced to three years in prison for this crime.
This money was actually paid to porn movie actress Stormy Daniels as hush money to induce her not to sell her story of having a sexual affair with Trump, a married man who later ran for president. Trump, after repeatedly claiming no knowledge of Cohen’s payment, finally admitted that he knew about it all along.
In fact, Trump and Cohen worked out an agreement under which the Trump Organization would reimburse Cohen by paying him “legal fees” for phantom legal services. Given Trump’s complicity in this crime, one would think that he too should have been given a stiff prison sentence. But as a sitting president, he was able to escape punishment.
When Trump leaves office, there are still other federal crimes for which he could be prosecuted. Among them would be obstruction of justice with regard to Robert Mueller’s Russia investigation, money laundering for Russian and Ukrainian oligarchs, soliciting and receiving campaign contributions and political assistance from foreigners, and illegally withholding military aid to Ukraine to force that nation to investigate Joe Biden and his son, Hunter Biden. And finally, Trump would be held legally responsible for his blatant interference with both the 2020 presidential election and with the transition of the presidency to his duly elected successor.
Trump's State and Local Crimes
Although cheating on your income tax is certainly a very serious crime, only a tiny percentage of the people caught cheating – whether on their federal or state income tax -- ever spend a day in prison. But New York State Attorney General Letitia James and Manhattan District Attorney Cyrus Vance Jr. have gone to great effort to secure most of Trump federal and state income tax returns from over the last twenty years. It would be fair to assume that they’re not thinking about just getting Trump to pay any back taxes he owes, or even assessing a substantial penalty.
They may also be investigating possible crimes involving bank and insurance fraud as well as money laundering. Trump, who has gone bankrupt four times, has been able to borrow from just one bank in recent decades – Deutsche Bank – which has lent Trump at least two billion dollars. The bank has an unwelcome reputation for having facilitated money laundering, and is reportedly cooperating with New York State banking investigators.
One possible route towards conviction and a prison sentence might stem from treating the $130,000 hush money payment as a legal expense not just on the Trump Organization’s books, but also on its New York State tax return, which Trump had signed. This would constitute tax fraud, and could result a two- or three-year prison sentence for the ex-president.
In recent years, about two dozen women have accused Trump of sexual assault. The problem with nearly all of these complaints was that the statutes of limitation had already passed. Still, upon leaving the presidency, Trump may be nit with a couple of defamation of character suits by women who claim he sexually assaulted them.
And so, while the successful prosecutive of sexual assault can result in lengthy jail terms – as it did for entertainment icons Bill Cosby and Harvey Weinstein, Trump is apparently in no legal peril for these crimes. Furthermore, even if he loses the defamation of character suits, at worst he will be forced to pay his accusers a few million dollars in restitution. What concerns Trump is the possibility of going to prison.
But a conviction for any state crime will probably take at least a couple of years, given Trump’s record of filing multiple appeals. Having taken part in some 4,000 lawsuits, he is probably already planning to fall back on that tried-and-true legal strategy.
Will Trump Be Able to Avoid Prison by Running Out the Clock?
Trump has a very long legal history of running out the clock by forcing his legal opponents through very lengthy and costly appeals processes. Indeed, that was his standard business model with small construction contractors whom he had stiffed by paying them much less than he owed them. Rather than go through a series of appeals to higher courts that they could not afford, most contractors caved to Trump’s demands.
Of course, that would not work with prosecutors, who would doggedly litigate through higher courts. But in the meanwhile, Trump would hope to postpone going to prison. As long as he could convince the court that he was not a threat to flee the country, perhaps Trump could run out the clock.
Trump, of course, has been thinking about running again for president in 2024, and considering his hold on the Republican party, his candidacy should certainly be taken seriously. If he could stretch out any criminal cases that will be made against him, he would appear to have a realistic chance of attaining four more years of immunity from virtually any legal jeopardy.
No one lives forever, even if they do exercise, eat well, and watch their weight. Trump at the age of 74, might need to be very lucky to celebrate his eightieth birthday. So using the lengthy appeals process in multiple cases might well keep him out of prison for the rest of his life. While perhaps not the retirement he had envisioned, it would still be a lot better than the one he deserves.
Will Trump Flee The Country To Avoid Going To Prison?
If, sometime after leaving office, Trump believes he is at imminent risk of going to prison, he could set up residence in a country that does not have an extradition treaty with the United States – like Russia, the United Arab Emirates, or some other friendly nation. While this would be a tacit admission of guilt, it would still be a lot better than spending years in prison.
If, on January 20th, Donald Trump stepped on a plane, no one could stop him from leaving the country. Even months later, he would be free to travel abroad without permission. But if, say a year after he left office, Trump were indicted for a serious crime, the prosecutor would ask the court to force Trump to surrender his passport, wear and ankle bracelet and be subject to house arrest.
So, we need to ask ourselves whether Trump might flee the country, and when he might flee. Despite the likelihood that a tsunami of lawsuits will mount against him, it is highly unlikely that Trump will be considered in imminent peril of house arrest throughout all of 2021. But the threat will surely hang over him in the coming months. And so, perhaps by early next year, Trump will step on a plane, wave good-bye, and never return.
Will Trump End Up Going To Prison?
Obviously, no one can really say for sure whether or not Trump will actually go to prison. We’ve discussed most of the subsidiary questions such as whether he will receive a presidential pardon from Joe Biden, Mike Pence – or even himself. Or whether he would ever be found guilty of serious criminal offenses.
Right now, the odds of Trumps ever going to prison appear to be considerably less than even. But during the next few months, a much clearer picture will emerge. It is said that it ain’t over till the fat lady sings. In this case, it ain’t over until the fat man with a one-way ticket heads for the airport. Or to prison.