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Trump’s Rough History With the Judge Determining His Fate



When former President Donald Trump heard that Justice Juan Merchan would be presiding over his criminal indictment in New York, he was livid.

“The Judge ‘assigned’ to my Witch Hunt Case, a ‘Case’ that has NEVER BEEN CHARGED BEFORE, HATES ME,” Trump wrote in a Truth Social post on Friday morning. Trump alleged that Merchan “railroaded” his former chief financial officer, Allen Weisselberg, into a plea deal. He concluded that he was “APPEALING!” the judge selection.

But far from the type of judge who strong-arms those who come before his court, Merchan has a widespread reputation for being as calm and collected as they come.

“He’s a very even-keeled guy. He’s thoughtful. He listens. Bright, kind of chill,” said New York City attorney Adam S. Kaufmann, who worked alongside him at the Manhattan District Attorney’s Office in the 1990s.

In court, Merchan’s tone is unwavering. He pauses often. He chooses how to phrase a suggestion or question carefully, so as to not seem biased. The cadence of his speech can be best described as adagio—gentle and just slightly slower than your average Manhattan criminal judge.

And yet, it’s true that Trump’s legal tactics absolutely set him off.


While presiding over the tax fraud trial of two Trump Organization companies in December, Merchan repeatedly lost his patience as Trump’s corporate lawyers broke the rules—leading witnesses, reading parts of transcripts jurors weren’t allowed to hear, and trying to distract the jury by duping them into thinking the case was about Trump the man, not his companies.


Judge Juan Merchan presides during the Trump Organization’s criminal tax trial last year.

Jane Rosenberg/Reuters

At one point during the trial, he repeatedly dragged Trump Corp. and Trump Payroll Corp. attorneys into a quiet sidebar to privately admonish them for making baseless objections to interrupt prosecutors—only to have them defy him minutes later, forcing the judge to send the jury out of the room.

“It’s your responsibility to make sure… this doesn’t happen again,” he warned them sternly.

He ultimately ordered the convicted companies to pay $1.6 million for dodging taxes, and he sentenced Weisselberg—who pleaded guilty—to five months in jail at Rikers Island.

“It was driven purely by greed. Pure and simple. The entire case was driven by greed,” Merchan scolded Weisselberg, a longtime Trump confidant who remained devoted to his boss for nearly 50 years.


Clearly, Merchan’s treatment of Weisselberg angered Trump.

In his post Friday morning, Trump spelled out the judge’s full name—the usual strategy he resorts to when painting a target on an enemy’s back. But in typical fashion, he misspelled “Merchan.” Critics immediately noted how Trump’s actions echoed his racist tirade against U.S. District Judge Gonzalo P. Curiel in California back in 2016, when he deemed that Curiel would be incapable of ruling fairly simply because he was born in Mexico.

But with Merchan, Trump can expect a judge who’s known by local defense lawyers and law enforcement for being “down the middle,” said former Manhattan prosecutor Catherine A. Christian.

“He has an excellent reputation,” Christian told The Daily Beast.

Merchan’s journey—and the people he met along the way—position him uniquely for the tall task now before him: presiding over a historic trial in which a former American president faces serious criminal charges that could land him in prison.

Merchan was born in Bogotá, Colombia, in 1962, when the country was still reeling from a decade-long civil war that killed 2 percent of all Colombians, a ghoulish period of mass torture referred to as La Violencia. His family relocated to Queens, New York, when he was only 6 years old and did what many immigrants do: start from the ground up. His father washed dishes at a local restaurant to provide for the family, according to Merchan’s future colleagues.

Merchan later went to Baruch College, but friends told The Daily Beast the journey was a bumpy ride. They said Merchan took several breaks from his studies to be a working dad who could provide for his own young family. When he finally finished law school at Hofstra University in 1994, he joined the Manhattan District Attorney’s Office at an extraordinary time.


Juan Merchan, center, as a member of the Manhattan DA’s rookie class of 1994.

Photo Illustration by Luis G. Rendon/The Daily Beast

The city was under siege with an unprecedented crime wave that had gone on for two decades. Mayor Rudy Giuliani and NYPD Commissioner Bill Bratton had just adopted the vicious “broken windows” policy of policing—cracking down on every minor infraction under the theory that little crimes lead to big ones. And it was up to these young assistant district attorneys to be on the front lines of that legal assault.

Defense lawyers were used to getting “turnstile justice,” said David G. Liston, a member of Merchan’s rookie class. “And we were the first or second class of ADAs who went into court and said ‘35 shoplifts is 35 too many. The defendant can plead guilty or go to trial.’”

“We were punching bags,” Liston continued. “We would get beat up every day we went to court. Judges would yell at us. Defendants would yell at us. But we all developed thick skins. If we thought we were doing the right thing, we were willing to deal with it.”

These exhausted young prosecutors would hit the bars after a long day—but not Merchan.

“As rookie ADAs, most of us were single and having lots of fun. But when we were getting beers he’d say, ‘I’ve got kids, I’ve got to go home.’ Very much a family oriented guy,” Liston recalled.

The onslaught of violent cases and round-the-clock prosecutions of even minor crimes flooded the courts and the jails, colleagues recalled. There were times when interpreters weren’t available at 2 a.m. to speak to someone involved in the case—and that’s when Merchan would shine. Fellow prosecutors remember how he’d translate their accounts from Spanish to English, ensuring that each person’s story was heard fairly and accurately, something he’d later take with him to the bench.


“There was sort of a dignity about him, a humility about him. He spoke with people in a way that made them feel respected,” Liston said.

After spending five years prosecuting crime, Merchan spent another five at the New York Attorney General’s Office, where he cracked down on fraudsters. In his final year there, Merchan nailed the owner of a fake GED home study course and shut down a scam modeling agency that roamed Long Island malls in search of impressionable parents who’d let them take photos of their kids who aspired to be models.

It may come as some surprise to MAGA diehards, but Merchan managed to avoid New York’s notoriously corrupt, Democrat-controlled judicial election system. That’s a system which subjects candidates to a shadowy system of politically charged interviews with local kingmakers—a far cry from the agnosticism that’s usually expected from would-be judges. In 2006, Merchan was actually appointed by then-Republican Mayor Michael Bloomberg, the party-switching billionaire who was known for putting moderates on the bench.

After spending some time in Bronx family court, Merchan became one of the first judges to run the city’s new mental health court, an experiment that embodied quite the opposite of “broken windows”—giving those accused of crimes a chance to get treatment for drug addiction and clinical behavioral issues.

“He was there back when it started, when dispositions for mental health treatment were not in vogue. He ran that courtroom. He took a risk on people,” Christian said.

Every defendant who appeared before him was a gamble. Give the wrong one a second chance, and an innocent person could get hurt—or worse.

“Depending on your mental illness, on a bad day, things can go south. Then you’re in the newspaper,” Christian said.


That’s where Merchan cemented a reputation for having a stoic approach, compassionate but firm.

Benjamin Thompson, a business lawyer in New York City, still remembers a pro-bono case where he represented a man who had a long history of arrests, constantly going in-and-out of jails and even fleeing from a halfway house. The man finally reached the end of the road when he stole a car and led cops on a chase. Merchan put him on the court’s recovery program, and kept checking on him for two years.

“Merchan was extremely patient and understanding. He picked the right times and right situations to be firm and stern,” Thompson recalled.

When the man completed the program, Merchan held something of a graduation ceremony. Everyone in the courtroom stood up, applauded and cheered.

“Judge Merchan is just one of the most wonderful people that I’ve ever experienced professionally. And one of the most deserving and appropriate people to be in a position of judicial discretion and authority,” Thompson said.

Merchan, who has now spent years overseeing criminal cases in Manhattan, is very familiar with Trump and his legal tactics. The way he handled the Trump Organization’s refusal to turn over evidence in the run up to its tax fraud trial shows his extreme caution and desire to avoid fanfare and media attention—even to the point of annoying the very office where he started his career. In late 2021, he held a secret, one-day contempt trial where he punished the company for failing to properly respond to the DA’s subpoenas. But he didn’t reveal its existence until the company lost the trial a year later—and even then, the court documents remain highly redacted.

Next week, he’ll finally face the real estate mogul behind the curtain, the man who’s been pulling the strings.


“You don’t want to disappoint him. He doesn’t yell. Never raises his voice. He speaks to you in a way that almost suggests you know better, you can do better, you are better,” Liston said.

Source: The Daily Beast

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