One of the great songs in the classic musical The Sound of Music was framed by a lyric sung by the head of an abbey about a nun who did things her own way: “How do you solve a problem like Maria?” As Judge Juan Merchan contemplates the upcoming sentencing of the leader of the MAGA movement, he too needs to figure out how to solve a problem like Donald Trump.
Solving that problem will require both legal acumen and a special kind of worldly prudence. The judge must first decide whether to go forward with Trump’s sentencing hearing now scheduled for September 18 and then determine what an appropriate punishment would be.
Last week Trump’s lawyer, Todd Blanche, sent a letter to the judge asking him to delay sentencing until after the 2024 presidential election. It offered several grounds for doing so, which, on close examination, are unconvincing.
Manhattan District Attorney Alvin Bragg responded by pointing out the holes in Blanche’s arguments but took no position on whether Trump’s sentencing should be delayed. “The People,” Bragg said, “are prepared to appear for sentencing on any future date the Court sets.”
In essence, Bragg told the judge that solving a problem like Donald Trump is the judge’s problem.
Whatever the legal merits of Trump’s request, the dictates of prudence are quite complicated. On the one hand, time before they cast their votes in November the American people deserve the know whether one of the major party candidates for President will be facing prison time.
On the other hand, a September sentencing hearing will offer the former President the kind of publicity boost that will re-energize his base. It may give him the chance to revive his flagging efforts to pin his real legal problems on his political opponents.
No one can know what the political atmospherics will be almost a month from now and in the aftermath of the September 10 debate. But, from the perspective of mid-August, it would be great if Trump was denied the opportunity to turn his sentencing into new political capital.
Whenever Trump is sentenced, he faces a range of possible punishments, “including community service, home confinement and up to four years in prison,” after having been convicted on 34 felony counts of falsifying business records. He did so to cover up hush money payments he made to Stormy Daniels ahead of the 2016 presidential election.
Those payments were themselves a kind of election interference. Trump hoped to avoid the exposure of his affair with Daniels before the votes were cast eight years ago.
Today, opinions about whether those crimes were serious enough to warrant jail time are sharply divided. For example, Norman Eisen, who was a lawyer in Trump’s first impeachment, and his colleagues argued in June that “a sentence of incarceration is warranted—not only for the seriousness of the crime but also because many other factors that influence sentencing also favor jail time.”
They noted:
Trump played a lead role in the scheme, has shown no contrition, violated a legally valid gag order during the trial 10 times, and has a history that includes civil verdicts for defamation, sexual assault and fraud. Deterrence of future misconduct for the defendant and others also counsels in favor of prison time, with Trump suggesting he may once again engage in election interference in 2024.
Former federal judge Nancy Gertner has a different view. As she sees it, the strongest argument against a prison sentence is that most of the other defendants who have committed similar offenses, especially first-time offenders, do not receive such a sentence.
Gertner says that the factors Eisen identifies are outweighed by what she calls “Trump’s unique position.” We shouldn’t, Gertner observes, “equalize the treatment of defendants by ramping up everyone’s punishment. Our criminal legal system is far too retributive and leans too heavily on imprisonment, no matter what the crime.”
A poll taken last month found similar differences of opinion among the American public. Of those surveyed, 48% thought that Trump should serve time behind bars for the crimes that were the subject of the New York prosecution, and 50% thought that he should not.
But resolving the question of when to go forward with the sentencing hearing may be as difficult and consequential as the sentence Judge Merchan eventually imposes.
Blanche’s letter to the judge requesting a postponement begins by replaying Trump’s groundless claims about what Blanche calls “the asserted conflicts and appearances of impropriety, which are also the subject of an ongoing congressional inquiry.” Blanche also asked the judge to consider “the significance of the 2019 conversations with Your Honor’s daughter criticizing President Trump’s use of Twitter, with the new fact being that existing Tweets from President Trump at the time of that conversation are squarely at issue in the pending Presidential immunity motion.”
And Trump’s lawyer wasted little time in focusing the judge’s attention on the unfolding 2024 campaign. He noted that, like Kamala Harris, “Tim Walz wrongly referred to this case in a public speech as the Democrat Party’s nominee for Vice President.”
And, in a real stretch, Blanche suggested that the judge has a conflict of interest because “In the same timeframe, Michael Nellis, a business partner of Your Honor’s daughter at Authentic Campaigns…, posted on social media about…making maximum donations to the Harris campaign and using his clout with that campaign to get Walz to ‘talk on our White Dudes for Harris call last week.’”
Blanche also said a postponement is warranted in light of the judge’s plan to rule on the implications of the Supreme Court’s presidential immunity decision on September 16. He claimed that postponement of the sentencing hearing was necessary “to allow President Trump adequate time to assess and pursue state and federal appellate options in response to any adverse ruling.”
It is, Blanche said, “unreasonable it is to have the potential for only a single day between a decision on first-impression Presidential immunity issues and an unprecedented and unwarranted sentencing.” He urged the judge to take notice of the fact that “Sentencing is currently scheduled to occur after the commencement of early voting in the Presidential election.”
Blanche’s letter ended by channeling his client. With a familiar Trumpian rhetorical flourish, he said that going forward with sentencing on September 18 would only serve what Blanche called “naked election-interference objectives.”
On the question of postponement of the sentencing hearing, Eisen comes down against it. He says that because “there is no basis for this latest delay under the law and Trump’s political purposes are so obvious, the court should reject this out of hand.”
Others agree that “If Merchan signs off on another postponement, it would be a huge victory for Trump.”
Surveys taken in the spring suggest that it may not be such a victory. They indicate that “a prison sentence could push more voters away from…[Trump] than a mere conviction…, but could also cause them to decide it’s overkill.”
It is hard to say whether these findings are still accurate. Most Americans, I suspect, are much less preoccupied with Trump’s New York legal troubles than they were several months ago.
And as we all know, the temper of our politics has changed a lot since then. Sentencing Trump next month threatens to disrupt this new mood, whatever sentence he receives.
In the end, as Eisen himself points out, Judge Merchan has enormous discretion in determining whether to move forward with sentencing or to grant Trump’s request for a postponement. The test Merchan must apply is “whether the delay is ‘reasonable.’”
The ingredients of that judgment are both legal and prudential. It will require what legal scholars, borrowing from Aristotle, call “practical wisdom,” namely “excellence in knowing what goals to pursue in the particular case and excellence in choosing the means to accomplish those goals.”
I have little doubt that Judge Merchan is a wise judge. But he faces an unenviable task.
As he considers both the goals and means of when and how to sentence Trump, he first needs to consider the legal and political ramifications of what would otherwise be the mundane task of scheduling a sentencing hearing.
It will take all his wisdom to figure that out and figure out how to solve a problem like Donald Trump. His decision about whether to move forward with the sentencing hearing as well as about what sentence to impose may tilt the scales in November in directions that neither he nor we can confidently predict.
