How Two Manhattan DA Classmates Hold Trump’s Fate in Their Hands

Indicted former President Donald Trump is currently on an extended episode of Law & Order—facing two people who lived through the real version of the drama.

The hard-nosed TV police procedural was originally inspired by the grim experiences of prosecutors at the Manhattan District Attorney’s Office during the tail end of a decades-long crime wave. The rookie class of 1994 saw it all, but two of those then-rookie prosecutors now stand out for a shared reason: They will both play decisive roles in historic criminal cases involving the former president.

One is Juan M. Merchan, now a New York Supreme Court justice who presided over Trump’s arraignment last week and is expected to oversee his trial next year for faking business records to cover up a hush money payment to a porn star.

The other is Jack Smith, the Department of Justice special counsel currently using a federal grand jury in Washington to investigate how Trump lied to the American people and inspired his followers to attack Congress on Jan. 6, 2021—and then hoarded classified documents at Mar-a-Lago once he left the White House.

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Merchan and Smith were classmates at the Manhattan DA’s Office, first-year lawyers who got their start just as Mayor Rudy Giuliani adopted the “broken windows” policing strategy—a severe crackdown on every imaginable minor crime under the theory that a steel fist would finally pound the cruising crime rate into dust.

Their fellow classmates told The Daily Beast that Merchan and Smith were reliable soldiers on the front lines of this new war on misconduct. That meant enduring shifts that sometimes stretched for two days at a time, late-night visits to multiple bloody crime scenes, and jumping into trials unprepared in a way that felt, as Shakespeare put it, like a daily return once more unto the breach.

”The training we got then—by virtue of the volume, pace, intensity—was something one could only get at that point in time,” said Georges G. Lederman, a former prosecutor who had been there for seven years by the time Merchan and Smith showed up.

Their boss was the legendary DA Robert Morgenthau, who ran that office all through the rising crime in the 1970s and 1980s, and then saw its precipitous drop over the next two decades. He was known for giving each incoming recruit a handshake with an accompanying line: “I ask of you only one thing: That is, to do the right thing.”

“Jack and I and everyone else were imbued with that one directive. That’s what we did, and that’s what he did,” Lederman said. “Jack stood out. He was a very methodical guy, very much a straight shooter. He made friends easily.”

At the DA’s office, recruits were split up into different bureaus—each with its own prestige and, at times, comical character. Former colleagues likened it to Hogwarts houses from Harry Potter.

The pensive and stoic Merchan, then a young father, was placed at Trial Bureau 60, which had a reputation for being cautious yet approachable. “They didn’t take themselves too seriously. Not zealots. Moderate,” one person recalled. It was the kind of formative experience that would perfectly suit a future judge.

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Meanwhile, Smith went to Trial Bureau 30, known for a gung-ho attitude of taking on challenging legal battles against all odds that four different ex-prosecutors described as “scrappy.”

“Thirty was not afraid of a fight, or of a difficult case. They were not afraid of losing. It was a badge of honor to lose a case now and then, because never losing a case meant never taking a hard one to trial,” remembered another colleague, David Liston.

In those days, an overworked prosecutor with two simultaneous trials that afternoon would regularly walk by a fellow assistant district attorney in the Hogan building’s narrow hallways and ask them to suddenly take a case. That kind of handoff was dicey, because volunteering to fill in meant taking on a case without the valuable experience of having conducted the actual investigation—something that took a decent amount of grit and a leap of faith.

Smith was always up to the task, colleagues said.

Karen Friedman Agnifilo recalled being pregnant with twins, fearing that going to one particular trial was just too risky; the defendant had attacked police officers, court security guards, and threatened prosecutors, plus, there was a chance she’d have to interrupt the trial with a sudden trip to the hospital delivery room.

“Of course, who steps in and says, ‘I’ll do it for you?’ Jack Smith,” she recalled.