Trump’s Shoot-the-Moon Legal Strategy

With less than a week to go before the start of his trial in New York on falsifying records, former President Donald Trump has sued Juan Merchan, the judge presiding over the case. The suit is sealed, but it is reportedly related to a gag order Merchan recently placed on Trump.

The suit seems highly unlikely to succeed, and it’s only the latest in a series of Trump broadsides against the judge. He accused Merchan of bias because the judge’s daughter has worked in Democratic politics, citing an account on X that the court says does not belong to her. In response, District Attorney Alvin Bragg asked Merchan to broaden an existing gag order, which barred Trump from attacking witnesses, jurors, and others, to also cover family members of the judge and the prosecutor. Merchan agreed, and ever since, Trump has continued to attack him. Last week, Trump also requested that Merchan recuse himself from the case, again citing the daughter. Merchan already rejected one recusal request last year.

[David A. Graham: Donald Trump’s ‘fraudulent ways’ cost him $355 million]

In the card game Hearts, the goal is to get the lowest score. Most of the time, a player succeeds by winning the fewest tricks. But a daredevil can attempt a different strategy, called “shooting the moon.” If, instead of losing each trick, he takes all of them, then his opponents all get the points and he gets none. It’s a risky maneuver, because it’s all or nothing—losing even one trick spells doom—but the reward is large.

Shooting the moon is also Donald Trump’s strategy for handling the legal cases against him. Ordinary practice would say that doing everything possible to antagonize the judges who oversee one’s trials is unwise. Even when a judge is not ruling from the bench herself, she has great leeway to decide what evidence is included, what arguments can be made, and what a jury hears. Yet Trump has repeatedly and personally criticized many of the judges hearing his cases. In addition to Merchan, he’s gone after Tanya Chutkan, the federal judge overseeing charges related to Trump’s attempt to subvert the 2020 presidential election. Trump also waged an extremely personal battle against Justice Arthur Engoron, who oversaw his trial on civil fraud charges in New York State. By contrast, he has not attacked Judge Scott McAfee, a white Republican man overseeing his trial in Fulton County, Georgia, or Judge Aileen Cannon, whom he appointed to the bench and who is assigned his case related to sensitive government documents he took from the White House.

The New York civil fraud trial shows the perils of this approach. In that case, Trump failed to request a jury trial, meaning that Engoron decided the verdict. Trump and his lawyers spent the trial demonizing Engoron, attacking his law clerk, and mouthing off in court. It didn’t end well. Engoron ruled that Trump had committed fraud and ordered that he pay some $355 million, plus interest. (Trump has appealed the decision.)

[David A. Graham: ‘Control your client’]

But Cannon shows the upside if Trump can prevail. He could hardly hope for a more amenable judge. She has repeatedly bogged down his prosecution, refusing Special Counsel Jack Smith’s attempts at speeding things up. More recently, she ordered both prosecutors and defense counsel to write jury instructions, a move that baffled many legal observers—partly because it is so early in proceedings, but especially because a portion of her order seemed to misrepresent the law. Her approach has frustrated Smith enough that prosecutors have begun sniping at Cannon in filings, which can’t help them.

Trump has a few incentives for his attacks. First, he faces the unappetizing task of having to explain to voters dozens of felony counts and the challenge of trials that keep him off the campaign trail. In response, Trump has decided to turn courtrooms into rally sites, portraying his prosecutions as politically motivated. Second, the facts of many of the cases are deeply unfavorable to Trump: He tried to subvert the election. He hoarded the documents and refused to hand them over. He flagrantly manipulated his property values. His attempt to get the hush-money case thrown out on statute-of-limitations grounds fell short. Trump might reasonably conclude that he’s likely to lose the cases, and so there’s little reason not to attack the judges.

In Trump’s best-case scenario—where he successfully shoots the moon—he is able to have judges he deems unfriendly thrown off the cases, or at the very least he is able to build a case to have convictions thrown out on appeal on grounds of bias. Then, perhaps, he’ll get a judge like Cannon who would be friendlier to him—or, in other words, much more biased.

But even if that doesn’t work, Trump may still be able to slow the cases. He’s already succeeded in pushing the election-subversion case back by months, thanks to a long-shot appeal to the U.S. Supreme Court. Merchan appears dedicated so far to keeping the New York case on track, but Trump also shows no sign of slowing down his dilatory exercises. He will continue to claim that judges are mistreating him, and place his supposed persecution at the center of the presidential campaign.

The shoot-the-moon strategy demonstrates anew Trump’s instinct for using a system’s strengths—such as opportunities for appeals, procedural arguments, and recusal motions—against it. Trump’s offensives against judges run counter to what most legal scholars and practitioners would advise, but the former president sees as an opportunity to subvert the criminal-justice system. It is diabolically clever: Trump hopes to so effectively label judges as corrupt that he will be able to actually corrupt the system and get a more favorable judge. Success would be the best proof of his point.