The most important date on Donald Trump’s July calendar isn’t July 4, when the nation celebrates its independence. Nor is it July 15, when the Republican Party convenes its national convention to christen Trump as its official standard-bearer for 2024. The most consequential date is July 11, when Trump will appear for sentencing hearing before New York state judge Juan Merchan.

Merchan will be faced with the historic task of deciding whether a former president should be sent to prison after being found guilty of 34 felony counts of falsifying business records in a prosecution brought by Manhattan District Attorney Alvin Bragg. Once thought to be the weakest of the criminal actions taken against Trump, the case has succeeded beyond expectations in holding Trump to account for his history of skirting the law. But while millions of Americans will be rooting for Merchan to throw the proverbial book at Trump, Merchan’s sentencing decision will not be easy, legally or politically. 

From a purely legal standpoint, Merchan’s decision will be one of first impression that will invite close scrutiny on appeal after a hotly contested six-week trial. The decision will also reverberate politically, exacerbating the country’s partisan divides, and strengthening Trump’s stranglehold on the GOP and the neo-fascist movement he leads.     

Under New York law, falsifying business records is ordinarily a misdemeanor. The offense is elevated to a class E (low-grade) felony when the falsification is undertaken for the purpose of committing or concealing an additional crime. The additional crime in Trump’s case is another New York statute that makes it an offense for two or more persons to conspire to influence the outcome of an election by “unlawful means.” 

From a purely legal standpoint, Merchan’s decision will be one of first impression that will invite close scrutiny on appeal after a hotly contested six-week trial.

Trump’s co-conspirators include his one-time attorney and “fixer” Michael Cohen,; former National Enquirer publisher David Pecker and Allen Weisselberg, the erstwhile chief financial officer of the Trump Organization.  Together with Trump, they hatched a “catch and kill” scheme in August 2015 to prevent the publication of any stories unfavorable to Trump as he campaigned for president in the 2016 election. As part of the scheme, Cohen paid adult film star Stormy Daniels $130,000 to suppress her alleged sexual encounter with Trump in 2006. The hush-money amounted to an illegal in-kind campaign contribution because it exceeded the 2016 limit of $2700 placed on individual contributions by the Federal Election Campaign Act, and the contribution was never reported to federal regulators.  

Given the jury’s unanimous verdict, Merchan will have several sentencing options. Each of the 34 counts carries a potential four-year prison term, with a maximum cap of 20 years. Merchan has the authority to impose any period of incarceration within the statutory maximum, but class E felonies carry no mandatory minimum sentences. Instead of sending Trump to jail or prison, Merchan will have the discretion to place Trump on formal probation, requiring him to report periodically to a probation officer, or grant him a “conditional discharge,” a type of sentence that sets conditions on his release but doesn’t involve in-person supervision. He could also sentence Trump to a term of home confinement or require him to perform some kind of community service plus a fine.   

Although Merchan will make the final decision, Trump will play an active and possibly decisive role in determining his punishment. In a very real sense, depending on how he behaves before July 11, Trump will hold the keys to his own future prison cell. 

Prior to pronouncing Trump’s sentence, Merchan will receive recommendations from the defense, the district attorney and the city’s probation department. The probation department conducted a virtual interview with Trump from his Mar-a-Lago home on June 10, and in the coming weeks,  it will prepare a pre-sentence report for Merchan’s review. As  in other felony prosecutions, the report will focus on such items as the nature of the offense, Trump’s personal history, and his willingness to comply with the terms of probation.

At the sentencing hearing, Merchan will balance and weigh the mitigating factors that militate in favor of a light disposition against the aggravating factors that point to incarceration. As attorney Norm Eisen, who served as co-counsel for the House Judiciary Committee in Trump’s first impeachment trial, has written, Merchan will begin with “the base line against which judges measure all sentences: how other defendants have been treated for similar offenses.” 

Eisen’s research shows that since 2015, the Manhattan district attorney’s office has filed over 400 cases of felony falsification of business records. Only one in 10 convictions, however, has resulted in incarceration. 

The infrequency of jail, along with Trump’s advanced age (he will be 78 at the time of sentencing), the absence of a prior criminal record and his service as a former president will count as mitigating factors.

Since 2015, the Manhattan district attorney’s office has filed over 400 cases of felony falsification of business records. Only one in 10 convictions, however, has resulted in incarceration.

On the other side of the ledger, Trump has been found civilly liable for sexually assaulting E. Jean Carroll. In addition, he has been ordered to pay $364 million ($454 million with interest) in damages as a result of the massive business-fraud lawsuit filed by New York Attorney General Letitia James that concluded earlier this year. He also has violated the limited gag order Judge Merchan imposed on him 10 times, resulting in two findings of criminal contempt. Even more significantly, he has shown absolutely no remorse for his conduct, and has vowed to exact revenge on his political rivals should he be reelected. 

On balance, the scales clearly tip against Trump. The key to obtaining leniency in criminal sentencing, even in cases where guilt is a close call, is to show respect for the system and the judge, and to demonstrate remorse. Aware of this cardinal rule, Trump’s lead lawyer Todd Blanche has obtained an order from Merchan permitting him to be present at any pre-sentence interviews to soften his client’s image and demeanor. 

It is all but certain that Blanche’s efforts will fail. Trump, according to many mental-health professionals, is a “malignant narcissist” who suffers from a disorder marked by paranoia, narcissism, antisocial personality and sadism. He is incapable of admitting fault, much less criminal responsibility. 

If Trump remains true to form, Merchan will have no choice but to sentence him to jail at Rikers Island or prison at one of New York’s 41 state correctional facilities for men. The sentence will likely be stayed while Trump’s appeal plays out, but will be imposed if the appeal fails. 

In the interim, Merchan can be expected to follow standard judicial practice in white-collar prosecutions and grant Trump bail on appeal, allowing him to run unfettered for reelection, and accelerate his unhinged attacks on the rule of law. The worst part of the entire process is not that a former president is now a convicted felon, but that he has convinced nearly half the country that the justice system is so thoroughly corrupt and rigged that the rule of law itself isn’t worth saving.

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