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Lock Him Up! Why Donald Trump Should Do Jail Time Before the Election

Granted, most first-time offenders who commit this particular crime don’t do time. But Trump isn’t most first-time offenders.

Trump speaks to the media at Manhattan Criminal Court
Steven Hirsch/Pool/Getty Images
Trump speaks to the media at Manhattan Criminal Court on May 30

Donald Trump stands convicted on 34 counts of falsifying business records in the first degree. That’s a class E felony. New York State sentencing guidelines say the punishment for committing a class E felony “shall be fixed by the court, and shall not exceed four years.”  If the convicted felon is not (as Trump is not) “a second or persistent felony offender,” then the judge “may impose a definite sentence of imprisonment and fix a term of one year or less.” 

The guidelines make no exception for former presidents. At Trump’s July 11 sentencing, Justice Juan M. Merchan should send Donald Trump to jail. I say “jail” because in New York State, sentences less than one year are served in jail, not prison. Trump can pursue the appeals process from his jail cell, as would anyone else.

My recommendation goes against what appears to be the rough consensus in the legal community. “Typically this is not the kind of case where you would expect a first-time white-collar offender to receive a sentence of incarceration,” Andrew Weinstein, a New York defense attorney, told Reuters’ Luc Cohen. Six legal experts advised Reuters that felony falsification of business records did not typically get first offenders jail time. When Weinstein represented such a client 15 years ago, the man got three years’ probation. 

Statistical evidence supports this conclusion. During the decade preceding Trump’s April 2023 indictment, the Manhattan district attorney brought 437 cases that included a felony charge for falsifying business records, according to a court filing. Manhattan criminal court records cited by Reuters’ Cohen show that four defendants who pleaded guilty in that period were sentenced to a year or less in prison. That’s less than 1 percent. Three of these four, unlike Trump, were also charged with other crimes, including fraud and grand larceny. The fourth was sentenced to one year of “intermittent imprisonment,” which meant he entered prison every Monday evening and left every Wednesday morning. 

For another survey, Norm Eisen, who was counsel for the first Trump impeachment trial, cast a wider net, reviewing nearly 10,000 cases since 2015 all over New York state. As with the smaller Manhattan sample, Eisen’s 10,000 cases statewide typically involved additional charges. So Eisen confined his review to those cases where falsifying business records was the most serious charge. The proportion of convictions in such cases that yielded prison time, he found, was not 1 percent but 10 percent. But that still meant that in 90 percent of cases similar to Trump’s, the conviction did not send the guilty party to prison.

Why, then, do I argue that Justice Merchan should send Trump to jail? Because Merchan won’t base his sentence solely on the similarity of Trump’s case to previous cases. He’ll also consider the many differences, and these are substantial.

The most obvious difference is that Trump did not plead guilty. That puts him in a different category from the four Manhattan defendants out of 437 who did jail time. Judges typically sentence defendants who plead not guilty more harshly than defendants who plead guilty.

Another significant difference is that Trump disrupted the trial proceedings at every opportunity. The judge had to impose a gag order barring Trump from discussing witnesses, jurors, prosecutors, court staff, family members of District Attorney Alvin Bragg, or members of Merchan’s own family. It’s pretty unlikely that defendants in those earlier cases incurred comparable prohibitions from the judge. It’s even more unlikely that these earlier defendants were found by the court to have violated gag orders 10 times, as Trump was. The $10,000 in fines that Trump paid did little to silence him, and at one point Merchan threatened to jail him for contempt of court. In the end, Merchan did not. Now that Trump’s a convicted felon, this misbehavior is reason enough to impose a jail sentence. 

Daniel Richman, a law professor at Columbia and onetime federal prosecutor in the Southern District of New York, told me he doesn’t expect Trump to serve jail time. But “in an ordinary case,” he conceded, “judges don’t take kindly to defendants who show contempt for the process.” Doing so, Richman said, would “argue strongly for coming down hard on someone.”

Another consideration is that Trump’s former attorney Michael Cohen spent more than a year at the Otisville Federal Correctional Institution as inmate 86067-054, then another year and a half under house arrest, for his own role in Trump’s hush-money transaction. Granted, Cohen was sent to jail not only for violating campaign law but also for tax evasion and making false statements to a bank. But it was Cohen’s covert payment to Stormy Daniels that brought prosecutors to his door. 

Compared to Trump, Cohen was “a less culpable person in terms of this crime,” Andrew Weissmann, a law professor at New York University (and former lead prosecutor in Robert Mueller’s special counsel investigation), told me. Trump was “the leader of the charged crime. This was all done for him.” Also unlike Trump, Weissmann pointed out, Cohen pleaded guilty (as Trump did not) and cooperated with the Mueller investigation (which Trump did only kinda-sorta). In addition, Cohen expressed remorse for his role in this crime. Trump, needless to say, has not, and indeed has done quite the opposite, insisting on his innocence, calling Merchan “corrupt” and “conflicted,” and much more.

Multiple news accounts have cited Trump’s age (he’ll be 78 at sentencing) as a reason not to send him to jail. It’s unusual, apparently, for 78-year-olds who falsify documents in the first degree to get jail time. This thinking requires updating. We also used to think it inadvisable for people older than 75 to run for president. The primary voters have spoken otherwise. If Trump is spry enough to serve a second term, he’s spry enough to do hard time.

News accounts have also noted that first offenders who falsify documents in the first degree seldom get jail time. Let us pause for a moment to appreciate how remarkable it is that a sociopath like Trump reached the advanced age of 77 before he received his first felony conviction. Bravo, Mr. President! That said, Trump has been pronounced a lawbreaker in too many previous civil proceedings to count. Just this year, Trump was found guilty of sexually abusing and defaming E. Jean Carroll in one such proceeding and defrauding banks in another. This second ruling is especially relevant to the hush-money case, given the common theme of deception. Fraud is a persistent refrain in anti-Trump litigation; seven years ago, you’ll recall, Trump paid $25 million to settle fraud claims against his bogus Trump University. Do you seriously expect Justice Merchan not to connect these dots? Past history and character, Eisen wrote, are legitimate matters for a sentencing judge to take into consideration, and in Trump’s case these cry out for jail time.

A final difference is the stakes. In those previous instances where New York state defendants falsified business records, the motive was theft, which is bad. Trump’s falsifications played out on a much larger stage. This crime, Eisen has observed, “could be seen not just as unfortunate personal judgment but also, as Merchan has described it, an attempt ‘to unlawfully influence the 2016 presidential election.’” Trump’s defenders say the New York criminal case was brought for political reasons. Of course it was! Trump’s falsifications may have put him in the White House! That makes Bragg’s decision to proceed with the case more defensible, not less.

Trump should go to jail not because of the ways what he did resembled previous offenses but because of the gaudy and appallingly singular ways they did not. In this as in so many other areas, Trump ventures where others dare not, then complains when the boom comes down that he’s being treated differently. He’s treated differently because he is different. He behaves worse than others do, and that misbehavior affects many more people. That’s why some voters love him, and others hate him. And it’s why he needs to spend time in jail. 

I think Merchan should give Trump six months. That way, should he win the 2024 election, Trump can be out by Inauguration Day. As I noted previously, in New York state a sentence of less than one year is served in jail, not prison. In New York City, the jail felons get sent to—white collar as well as violent criminals—is Rikers Island. I’m fine with that. If it’s good enough for Trump’s former chief financial adviser Alan Weisselberg, age 76, who’s got three months left to go there on his five-month Riker’s sentence, it’s good enough for the boss. Let’s give them some quality time together.