Criminal Justice

The Trump hush-money trial's greatest misses

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Former President Donald Trump at his hush-money trial

Former President Donald Trump, flanked by defense attorneys Todd Blanche, left, and Emil Bove, in court in Manhattan last month. (Jabin Botsford/The Washington Post)

Over 20 days at Donald Trump’s hush-money trial, the prosecutors, defense lawyers, and even the judge have had strong moments, but also times when they’ve faltered or been caught off guard, according to legal experts who have been tracking the case.

In trials, a lawyer’s mistakes can sometimes be more consequential than their successes. The jury will hear closing arguments Tuesday and then deliberate in hopes of reaching a verdict about the guilt or innocence of the former president and presumptive 2024 Republican nominee.

Even before that critical juncture in the nation’s political and legal history, certain moments from the five-week trial that is focused on hush-money reimbursements already stand out to veteran litigators, not as the greatest hits—but as the greatest misses.

Lawyers know the first trial of a former U.S. president will be picked apart for years to come by pundits, politicians and historians.

“If they win, then everything they did was brilliant—every word they spoke or didn’t speak was gold,” Ronald Kuby, a longtime criminal defense lawyer in New York, said of the lawyers working for Manhattan District Attorney Alvin Bragg (D). “And if they lose, they are a bunch of suckers who had no business trying this case.”

Here’s a look at some of the missteps that may matter most:

An angry, demanding defendant

“Whatever else Donald Trump may be—a great businessman, a great reality TV show host, a great politician—he’s a dumb lawyer,” said Jim Walden, a former federal prosecutor now in private practice.

Walden, like many New York lawyers, said Trump appears to have had too large a role in the defense strategy, often to the detriment of his chances of success. Trump’s biggest mistake, several lawyers said, was constantly attacking New York Supreme Court Justice Juan Merchan outside court, and having a body language of disdain toward him in the courtroom.

“The thing that I think Trump just doesn’t get is, even if you don’t like the judge, the jury is going to like the judge,” Walden said. “When you’re super disrespectful to someone the jury sees as a professional person doing their job, that’s a self-inflicted wound.”

Trump also appears to be driving too much of what his lawyers say in court, Kuby said.

“I am very candid with my clients, and tell them: ‘I don’t teach you how to sell drugs. Don’t teach me how to cross-examine a witness,’” Kuby said. “It is a fundamental mistake to take orders about trial conduct from the client.”

Prepping for text messages

The Manhattan district attorney’s path to charging Trump with 34 counts of falsifying business records was a tortured one. Plenty of lawyers have questioned the wisdom of basing a historic indictment on conduct that federal prosecutors examined years earlier and decided did not merit charges against Trump.

According to people familiar with the discussions who spoke on the condition of anonymity to describe internal deliberations, federal prosecutors declined to charge Trump for two chief reasons: The key witness, Michael Cohen, was simply too untrustworthy; and the Justice Department’s prosecution of a case with what they viewed as stronger facts against a different politician, former senator John Edwards (D), had failed.

The district attorney’s theory of their case—that Trump falsified records of his reimbursement of Cohen to cover up an election-related crime—is complex. The stakes are high, and one member of the team, Matthew Colangelo, came into the case untested as a prosecutor.

But the prosecution’s worst moment, according to legal experts, was when Cohen was confronted on the stand with text messages that called into doubt his testimony two days earlier about what he said was a 2016 phone conversation with Trump about a plan to pay $130,000 in hush money to porn actress Stormy Daniels.

The text messages to Trump’s bodyguard were about an entirely different matter, harassing phone calls, raising questions about whether the brief phone call that followed would have given Cohen enough time to also discuss the hush-money plan with Trump.

“The prosecution blew it by not preparing Cohen better for those text messages,” Walden said. “That’s what witness preparation is all about, and it seemed to me that Cohen was really poorly prepared for that.”

Another weak moment for the prosecutors, Kuby said, was when Cohen described his decision to steal $30,000 from Trump as “self-help.”

“In retrospect, I think they could have done a bit better on that,” he said.

Trials, however, are not scripted; there are always some surprises, and prosecutors often have to adapt, improvise and recalibrate. Kuby said he was impressed with how well the assistant district attorneys have done that.

“Overall, it’s the smoothest prosecution case I’ve ever seen,” Kuby said.

Directing the defense

It has become something of a parlor game in New York legal circles to try to determine which questions or statements by Trump’s lawyers were pushed on them by the former president, particularly when it came to the cross-examination of Daniels.

Trump’s lawyers pressed her at length, seeking to portray her as a greedy person looking for fame and a payday from her long-ago alleged sexual encounter with the reality TV star who would go on to become president.

Many defense lawyers have argued that tactic was a mistake that could backfire with the jury, because Daniels knows nothing about the crux of the case—a series of payments made to Cohen in 2017, reimbursing him for the hush money, which prosecutors say added up to criminally falsified business records.

Trump’s lawyers, however, insisted on trying to show in court that Daniels never had sex with Trump—echoing the former president’s longtime claim. That decision, prosecutors said, opened the door to asking Daniels about what happened that night, putting potentially damaging details in front of the jury—including that the sex may not have been fully consensual.

Walden, who once prosecuted mob cases in Brooklyn, said the most significant defense error was calling longtime lawyer Robert Costello to the stand, ostensibly to undermine Cohen’s credibility. Costello infuriated the judge as he tried to tell the jury about his 2018 conversations with Cohen about the hush money payments, rolling his eyes or audibly protesting when the judge said certain questions or statements were not appropriate.

“Costello was a disaster,” Walden said. “The defense finally got some momentum, and it all got dialed back because Costello was playing to Trump instead of playing it straight. He had a good story to tell, and instead they put the throttle right back in the prosecutor’s hands.”

One quirk of the Trump trial is that his lead attorneys, Todd Blanche and Emil Bove, are veteran former federal prosecutors with little experience defending a case in state court; at one sidebar early in the trial, Bove asked for patience from the judge because it was his first time cross-examining a witness as a defense lawyer.

And Bove and Blanche both consistently referred to prosecutors not as “the people,” but as “the government,”—a federal court term that sounds like nails on a chalkboard to most state court practitioners.

A judge in the hot seat

Even before the trial began, it was clear Merchan was deeply irritated with Trump’s lawyers.

That irritation was on full display during a hearing about Trump’s repeated violations of a gag order early in the trial, as Merchan expressed his frustration with Blanche’s argument.

“Mr. Blanche, you’re losing all credibility,” Merchan told the lawyer.

To Walden, that was the judge’s low point in the case.

“I understand he felt that way, I just think it was an unnecessary, emotional reaction in a situation that really required his best game,” Walden said.

There were a few other big moments when Merchan abandoned his low-key approach.

When Costello was on the witness stand and visibly annoyed with the judge, Merchan gave him a tongue-lashing, then became even angrier when Costello stared back.

“Are you staring me down right now?” the judge asked incredulously. “Clear the courtroom,” he ordered.

But the only people removed from the courtroom were the reporters and members of the public. Trump’s supporters were allowed to stay to watch Merchan warn Costello that he was coming dangerously close to being held in contempt.

Among the Trump entourage that stayed in court was law professor Alan Dershowitz, who promptly wrote a column in the New York Post calling Merchan’s conduct “outrageous, unethical, unlawful and petty.” He expressed bafflement as to why he was allowed to stay in court while the reporters and public had to leave.

Just last year, a New York appeals court overturned a murder conviction in the same courthouse because the trial judge improperly closed a courtroom—a decision that oddly also involved concerns about staring. In that case, however, the courtroom was closed for days, not minutes.

Some lawyers think Merchan also came dangerously close to giving Trump a meaningful issue on appeal when he let prosecutors question Daniels at length about the details of her alleged sex with Trump, offering an account that could be more prejudicial than relevant.

Kuby, however, said that line of questioning was fair game, though he noted: “There are pro-prosecution judges, and the problem with those judges is that not everything the prosecution wants is good for them.” Even with a judge’s blessing, prosecutors can still overplay their hand and alienate jurors or mishandle a witness.

Overall, he said, Merchan has done “an amazing job of being fair in his rulings, being thoughtful, and explaining the bases for them.”

What matters ultimately, of course, is not what observers think of the lawyers, but what the jurors think of the evidence, and that is unknowable for now.

“During a trial, you have no concept of how the testimony landed or its significance, until the jury reaches a verdict,” Kuby said. “You’re speculating about what’s going on in the minds of 12 people that you’ve never met.”

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