The Unpopular Position

In 2007, Cesar de Castro was five years into his tenure as assistant district attorney in the Manhattan DA’s office when he heard that the Deutsche Bank Building in Lower Manhattan, abandoned since 9/11, had caught fire. 

It happened in the midst of a complicated deconstruction, one floor at a time, to remediate asbestos and other contaminants. As firefighters battled the blaze, rapidly spreading from the 17th floor, the building’s standpipe system wasn’t working correctly. Water was being pumped in only to wind up on the basement floor. The fire burned for days. Two firefighters died.

In its aftermath, de Castro’s boss, legendary Manhattan DA Robert Morgenthau, announced an investigation into criminal allegations connected to the fire. “I didn’t think it was going to be me, and then it turns out it’s going to be me,” de Castro says of the 18 months he spent investigating with a team of 30. “I was lead counsel for a while.”

In the rackets bureau, de Castro had handled cases in the news, but not with this level of public pressure.

“I started to develop an opinion on the case, as you do as a prosecutor in terms of what you have,” he says. “The law in the area of manslaughter and criminally negligent homicide is complicated; it’s not as straightforward as ‘Two firemen are dead and someone has to pay.’ I didn’t think it should be a criminal case. It was tough for me. I had a really tough time personally with having the courage to say, ‘I don’t think this case rises to the level of a criminal indictment.’”

When he did make that opinion known, de Castro says, he was promptly removed from the case and encouraged to take a vacation. “That’s how I left,” he says of his move to private practice.

It’s a story he’s never told publicly and the first one that comes to mind when asked about lessons he’s learned as a prosecutor.

“Part of being a lawyer is dealing with the unpopular position,” he says. In private practice, he’s represented clients like developer Fred Daibes, convicted of bribing Sen. Bob Menendez; executives accused of fraud in the Dewey LeBoeuf collapse; and a Mexican official sentenced to 38 years in federal prison for accepting millions in cartel bribes.

“I know how the prosecutor’s view can get skewed given the notoriety,” de Castro adds. “Anybody working on something when you know they’re watching your every move, it’s hard to remain objective. So I try to take that experience and channel it on this side.”

The Deutsche Bank fire prosecutions, with criminal indictments, proceeded without him. “Everyone got acquitted,” he says.

De Castro was born in Westchester County to Dominican immigrants, grew up in Honesdale, Pennsylvania, a place known for its summer camps, and attended Penn State with plans to go to law school if a career playing pro baseball didn’t pan out. (He hit .533 in high school.) To this day, he puts trial losses in perspective by comparing them to batting averages.

Attending New York Law School for its proximity to downtown courthouses—“I really wanted to see law in action,” he says—he completed internships with two U.S. attorneys offices (Eastern and Southern), as well as the Eastern District Court, before making it through the five-interview process for the Manhattan DA’s office. The last interview was with Morgenthau himself. De Castro was anti-death penalty; in law school, he had written a newsletter featuring stories about botched executions and other anti-death penalty facts, which he posted around campus and stuffed in professors’ mailboxes.

Morgenthau brought this up. He asked what he’d do if he were asked to work on a case where they were seeking the death penalty.

He told Morgenthau: “I can’t do it. I’d ask to not do it.”

And Morgenthau said, “Good, you’re hired.”

First, de Castro spent two years with the U.S. Court of Appeals for the 2nd Circuit, churning out three memos a week advising the court on pro se cases. “Every memo is to three different judges,” he says. “Some are like, ‘What is all this annoying detail? I don’t need any of this to decide this.’ But there are some who say, ‘I want all the details. I want everything that happened in the district court.’ So we have to know our audience.”

It was only after those two years, and a second round of interviews, that he joined the Manhattan DA’s trial division and then its rackets bureau. He conducted long-term investigations into organized crime and corruption schemes. 

Morgenthau, in his late 80s, was still personally signing off on all wiretaps. “He reviewed every single one,” de Castro says. “It was amazing. … He knew the details and would ask you questions.” 

Later, after de Castro went into private practice, he wrote an article for the New York Law Journal, unpacking the law on criminally negligent homicide prosecutions, and Morgenthau, seeing him in the DA’s office one day, came over to tell him it was well-written. “He was such a gentleman,” de Castro says. “I grew up in such a gentleman’s practice. You gain relationships with the defense bar. You take your positions and you understand these are hard decisions to make.”

At Tarter Krinsky & Drogin, de Castro defended Testwell, a company that had been indicted by his former bureau for allegedly faking concrete strength results. He then moved to Lankler Carragher & Horwitz before starting his own firm in 2012.

He’d just been appointed to the Southern District’s Criminal Justice Act Panel when Sharon McCarthy of Kostelanetz tapped him to help defend Denis Field, the former CEO of the accounting firm BDO Seidman. “Four years at the DA’s office is nothing compared to doing one trial with her,” de Castro says of the amount of preparation required.

Field had already been tried and convicted on conspiracy and tax evasion charges connected to the $7 billion Jenkens & Gilchrist tax shelter case; but because of juror misconduct—a disbarred lawyer lied to get on the panel—the judge ordered another trial with new lawyers. And while the government’s case stayed the same, the defense focused less on tax-shelter technicalities than on the lack of evidence connecting Field to the conspiracy. De Castro calls it the “dot dot dot” defense—criticizing the prosecution’s claim that even though Field’s name did not appear on any of the emails, his name was probably below the ellipses of the “To” line.

“The client had shirts made that said ‘dot dot dot,’ and he even wore a polka-dot tie,” de Castro says. “At his acquittal, he took it off and handed it to me. I have it in a case in my office.”

Next, he joined the defense team for the Dewey LeBoeuf fraud case, a six-month trial in which he helped secure acquittal for CFO Joel Sanders. In a 2017 retrial, Sanders was found guilty of securities fraud and conspiracy but avoided jail time.

Both cases were huge learning experiences, de Castro says, but his hardest case to date—in terms of both pressure and loss—was representing Genaro Garcia Luna, the former secretary of public security for Mexico, who was charged in the U.S. with taking cartel bribes. Minutes after de Castro was appointed to the case as a CJA, he was getting phone calls from news organizations. At trial, reporters were lining up at 3 a.m. to get into the courtroom.

“To be under that microscope, and trying to limit exposure so people would be willing to help us and tell the truth, was really hard to navigate,” de Castro says.

More so, he says, as he realized the situation facing his client. “This was a case where the government was saying the client had taken hundreds of millions of dollars in bribes from the cartels, and they did not corroborate anything with a single message, text, nothing,” he says. “It was just the words of cooperators, who have admittedly killed collectively more than 5,000 people—probably the most murderers who have ever been put together in a trial in the Eastern District, and that’s saying something. Gotti, Sammy the Bull had nothing on these guys. They kill everybody, and they admit to it, and my client had been instrumental in all their extraditions to the United States. Many of these people had been talking to the government for a decade. There were tens of thousands of single-spaced pages of interview reports that talked about corruption and had never mentioned our guy—until all of a sudden, more recently, when the U.S. government wants to indict him.”

At trial, de Castro’s strategy was to hammer that point home with every witness. One cooperator had never named his client but had mentioned bribes to other politicians—including Mexican President Andrés Manuel López Obrador. In cross, when de Castro asked about that, the courtroom erupted.

“That’s when the massive attacks began, [people] screaming at me, ‘How dare you accuse our president of this?’ These are reporters, people from the embassy. I’m getting calls saying they’re going to pay people to have me killed.”

The Mexican president called him a thug and sent a “passive-aggressively threatening” letter that still hangs on de Castro’s wall, but de Castro held his ground. “I think all the prior experiences helped me keep my head and lead the team, do the interviews at the right time with the right people,” he says. “It’s tough, but you have to do your thing. You have to do what’s right for the client.”

He knew the odds. “The government wins 98 percent of the three percent of cases that go to trial,” he says. “You have to put that aside. You go into believe mode.”

In 2023, Garcia Luna was convicted on all charges and sentenced to 38 years.

“Every loss is a gut punch and having to stand there with a client and getting those guilty verdicts, it is very, very painful,” he says. “Most people turn their backs on them. A lot of the support they thought they had they don’t have. There’s press all around them, people who have cooperated against them. They can’t trust anybody. They trust you.”