Jail to the former, and maybe future, chief

US

“I believe a stiffer sentence [than five months in jail] is warranted having heard the evidence,” said Justice Juan Merchan to Trump Organization CFO Allen Weisselberg on Jan. 10, 2023, after the Trump Organization criminal trial. Fortunately for Weisselberg, Merchan accepted a plea agreement for a five-month sentence before the trial started, although he pointedly said “Had I not made the promise, I would be imposing a sentence much greater ….”

Those remarks provide guidance as to what Merchan may do when it comes to sentencing Donald Trump — a defendant far more entangled in corruption than any of his underlings.

Like Trump, Weisselberg was a first-time offender. It did not keep him out of jail. And Merchan rejected a plea for a lesser sentence based on Weisselberg’s age of 75 (Trump is 78). Unlike Trump, who purports to enjoy the most robust good health imaginable, Weisselberg’s lawyers claimed he was in “far from perfect health” in a futile attempt to obtain a sentence less than the promised five months.

This should be a klaxon-sounding and red-lights-flashing warning to Trump that a jail sentence in this case is not merely a technical possibility; it is more than likely.

As an ordinary convicted felon who is not a former president, Mr. Donald J. Trump makes a remarkably compelling case for incarceration. While all of his 34 felonies were committed in furtherance of a single scheme, they involved separate, repeated, and deliberate criminal acts spanning over a year; not a solo bad choice born of impulsivity.

Judge Juan Merchan, right, speaks to Donald Trump regarding his contempt ruling in Manhattan criminal court, Monday, May 6, 2024, in New York. (Elizabeth Williams via AP)

While many defendants can obtain a measure of leniency by showing their criminality was a product of mental illness, drug addiction, or simple desperation; no such avenues are available to Trump. His crimes were motivated by a desire to benefit himself by corruptly influencing a basic feature of American democracy.

Merchan excoriated Weisselberg’s “naked greed” in imposing sentence; Trump’s attempt to steal the presidency is a whole different level of bad. And Merchan is unlikely to look favorably on Trump’s insistence that everything he did, he did for the good of the country.

There is also Trump’s continued insistence that he did nothing wrong and that he is a “very innocent man.” Convicted felons can continue to maintain their innocence and show no remorse. But sentencing courts regularly look askance at relentless insistence of innocence after a jury decides otherwise. After all, if Trump believes he did nothing wrong, only the law’s strongest sanction may deter him from future fraud.

Courts also look to the need to deter others. Most crimes of this type involve defendants who cook the books to cover-up embezzlement or other financial crime; arguably far less serious to society than Trump’s conduct. Failing to jail Trump would gut the carceral sanction; if he does not get a jail sentence for his massive, on-going, systematic fraud designed to purloin the presidency, who should? The accountant on the third floor? The secretary?

Sentencing courts also consider it an aggravating factor when a corrupt defendant suborns other people into their scheme. Trump, of course, enlisted many others into his frauds, from the eager, bootlicking Michael Cohen to the young and star struck Hope Hicks.

Finally, there are Trump’s attacks on the criminal justice system and everyone (and their families) involved in it. While Merchan has already punished Trump for his gag order violations, Trump’s total and utter contempt for the entire process, seldom seen in any American courtroom, is a legitimate factor to consider when deciding whether to send a defendant to jail.

Should Merchan choose a term of incarceration as part of Trump’s sentence, there is zero chance that Trump will be carted away on July 11. Thanks to New York’s liberal bail laws (which should have a new fan), Trump will remain free on his own recognizance until an entire raft of appeals are decided by various courts in a process that will take years.

Despite conservative attempts to “toughen” these laws, the only legitimate purpose of bail in New York is to ensure that the defendant will appear — at trial or execution of sentence — when he is required. And although many wish he would flee, Donald Trump is not a flight risk.

At some point, though, that steel jail door is likely to slam shut.

Kuby is a New York-based criminal defense and civil rights lawyer.

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