Alvin Bragg’s Next Decision on Trump Presents a Political Quandary

NEW YORK — Alvin Bragg, the Manhattan district attorney, went into former President Donald Trump’s hush-money trial besieged by death threats from extremists, reproval from political commentators for creating a national distraction (“Save the mug shots for Georgia, the handcuffs for Jan. 6,” wrote Peggy Noonan in The Wall Street Journal) and criticism from legal analysts who saw the case as structurally unsound, too quixotic to proceed. The result nevertheless was a guilty verdict on all 34 counts of falsifying business records in the name of concealing a shady scheme to disrupt the 2016 election.

The district attorney’s work will soon turn to the sentencing memo his office will present to the judge in the case, Juan M. Merchan, which ought to prove equally controversial no matter what it recommends. Trump was convicted of class E felonies, the lowest level in the state, and could be sentenced to probation or up to four years in prison — or, alternatively, what is known as a split sentence, with a relatively brief amount of time spent in a city jail in advance of a probationary determination. (The notion of a former president and his requisite Secret Service detail all piling into Rikers Island is unlikely.)

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Certainly to be considered is the fact that Michael Cohen, one of the executors of the conspiracy for which Trump served as impresario, was sentenced to three years in federal prison — though he ultimately did not serve the full term — after pleading guilty to campaign finance violations and lying to Congress. Last year, Allen Weisselberg, the former chief financial officer of the Trump Organization, spent 100 days in jail after pleading guilty to tax fraud involving his former employer — also a “paperwork” violation. And he was sentenced to jail time again in April, in accordance with Bragg’s recommendations, after pleading guilty to perjury in Trump’s civil fraud trial.

The political consequences around this issue are layered, both in terms of the presidential election and Bragg’s own career. Unlike a federal prosecutor in a similar position, Bragg is an elected official. (Granted, history provides no analogous example of a county prosecutor weighing in on the fate of an ex-president with a criminal conviction.) Should he bend toward leniency, he faces the potential backlash of the Trump-hating Manhattan Democrats who would keep him in office. Should he lean into harsh punishment, he faces charges of hypocrisy from legal purists as well as a vast Trump support system, which, as one former prosecutor put it, would raise millions of dollars instantly off the designation of a maximum sentence.

Bragg is a well-known reformist who has built his reputation on turning away from the prosecution of low-level street offenses and championing anti-carceral approaches to criminal justice. What would it mean for him to send a 77-year-old man with no prior criminal record to prison?

“It’s a sad day to put anyone in jail. ‘Lock him up’ — we don’t believe in that,” Duncan Levin, a former Manhattan prosecutor turned defense lawyer, told me. “A conviction of a former president is sad,” he added, and the task of sentencing him is one “you wouldn’t wish on anyone.”

Still, Levin maintained that he struggled “to imagine an E felony case that calls out for jail time more than this one.” He pointed to Trump’s three pending indictments, his lack of demonstrated remorse — which is given considerable attention during sentencing decisions — and the several times he was held in contempt during the trial.

“You can criticize the DA for asking for jail time as politically motivated,’’ Levin said, “But it doesn’t mean that Trump doesn’t deserve it.”

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