The Famous New York Defense Attorney goes to prison. Robert Simels

From Elite Prosecutor to Federal Prison

Robert Simels had a dream job in the 1970s. He was part of an elite anti-corruption prosecution office in New York City, going after dirty cops, crooked judges, and corrupt politicians. “When you’re a prosecutor you always think you’re on the side of the Angels,” Robert told me. “You see everything in Black and White terms and a guilty person’s a guilty person and no matter what you think about them that’s the way you view them.”

But that righteous certainty would eventually become his downfall.

Robert’s office was created after hearings showed the New York City Police Department was almost entirely corrupt. Think Serpico, but bigger. With 35 attorneys and 100 investigators, they were the princes of the city. The press loved them when they went after cops. Then they started targeting judges, politicians, and lawyers.

“At that point we weren’t so popular anymore,” Robert said. He was in his twenties, indicting 11 judges and causing the police commissioner and 25 senior officers to resign. The myth of their power grew beyond reality. People believed they had bugs and wiretaps all over the city. They didn’t, but fear spread anyway.

Then politics intervened. A new governor called their boss in on December 23rd, 1975. They thought they were getting statewide jurisdiction. Instead, the boss came back and said he’d been fired.

Robert switched sides.

The Defense Attorney Who Actually Won

Most defense attorneys don’t win federal cases. The feds lose cases when prosecutors make mistakes. Robert knew this because he’d been one of them. His approach stayed the same, just applied differently.

“I said to myself I’m good enough I can compete against anyone and all I have to do is follow the same footprints that I use as a prosecutor and I should be successful as a defense attorney,” he explained.

Federal court is a different world than state court. The Southern District of New York has 50 prosecutors compared to 500 at the Manhattan DA’s office. They only hire from big firms, requiring two years of private practice first. It’s an elite group.

Robert specialized in big narcotic cases, mostly representing people of color. This didn’t endear him to the government. “The system is and continues to be very Prejudice,” he said plainly. The government disliked him more for representing those clients than if he’d represented white defendants charged with the same crimes.

His method was thorough to the point of obsession. In one case, he kept the government’s principal witness on the stand for nine days. When they had a two-month wiretap, most attorneys would just listen to the recordings the prosecutor wanted to use. Robert listened to every single hour and hired a black professor who studied urban ethnography to help him understand the language and culture.

The details mattered. The witness claimed to be in Queens negotiating a drug deal, but the tapped phone was in Manhattan. She was lying to make herself sound more important. “Every instance like that I pointed out that the agents weren’t listening to their own stuff,” Robert said.

The Henry Hill Case That Changed Everything

On Memorial Day weekend 1980, Robert got a call that would reshape his career. He was probably the only attorney in New York not vacationing in the Hamptons. A judge’s office asked him to witness someone signing a document at Brooklyn Federal Courthouse.

That someone was Henry Hill.

Henry faced four life sentence indictments for narcotic trafficking. The feds wanted him to plead guilty to become a more credible witness. Robert talked to Henry and told the prosecutors he wouldn’t plead guilty to anything. They didn’t like it, but Henry signed the cooperation agreement anyway.

Then Nassau County broke the deal. Robert moved to dismiss for prosecutorial misconduct. Federal attorneys warned him not to make enemies of the Nassau County DA. “I said I don’t care,” Robert recalled.

The hearing had helicopters over the courthouse, SWAT teams outside, and marshals with automatic weapons in the courtroom. Robert subpoenaed an assistant DA’s notes from a meeting where the district attorney essentially said “screw the feds, we’ll get no publicity if we don’t continue to push our case.” The judge dismissed all charges against Henry.

But representing the biggest rat of all time cut Robert out of mafia work forever. “There are three kinds of clients,” he explained. “White collar clients, people of color involved in narcotic trafficking, and the mafia. By representing Henry I cut out that whole mafia segment because they wouldn’t hire the guy who represented the biggest rat Of All Times.”

So Robert helped Henry write a book. After shopping it coast to coast, he finally got a meeting at Simon and Schuster. The head editor said they didn’t do mafia stories and would never publish it. Then the head of the company burst through the door, heard the pitch, and said it was the greatest story he’d ever heard.

The book became “Wiseguy.” The movie became “Goodfellas.”

Taking on the Bush Administration

Robert’s most audacious case involved Christopher Drogoul, a banker accused of loaning Saddam Hussein billions through a small Atlanta bank office. The government claimed Drogoul did it all himself, without anyone knowing.

“You can’t borrow billions in America without the FED knowing about it,” Robert pointed out. “You can’t even deposit $5,000 anymore without the government knowing about it.”

Deep within the CIA, people started feeding Robert information. The deputy director of the CIA, Admiral Bobby Ray Inman, called him up. They met in an empty ballroom at the St. Regis Hotel in New York. Inman told him exactly what document to write to scare the government, proving Robert had backdoor access to classified information.

Robert subpoenaed President George H.W. Bush, Secretary of State James Baker, National Security Adviser Brent Scowcroft, and Henry Kissinger. Kissinger called personally: “Do you know who you’re talking to? Do you know who you subpoenaed?”

The 11th Circuit Court of Appeals agreed Robert could subpoena the president. When the Clinton administration took over, Attorney General Janet Reno called offering a six-month plea instead of life imprisonment. Drogoul took it.

He was poisoned and died after his release.

The Case That Sent Him to Prison

Robert’s reputation grew with each victory. In federal prison, word travels fast about which attorney actually wins. But that reputation also made him enemies in the prosecution ranks. Every case built their ire.

The government kept subpoenaing him, claiming he was unethical because they couldn’t believe he could win unless he was doing something improper. “I would say no I’m not doing anything other than proving that you’re not doing your job which would only make them unhappy,” he said.

Finally, representing drug kingpin Shaheed Khan from Guyana, Robert was charged with attempted witness tampering. He received 14 years.

The nightmare he’d helped so many others navigate became his own reality.

Since his release, Robert has worked as a legal consultant, hosted a radio show, and spoken at Yale University. The prosecutor who thought he knew right from wrong in black and white terms learned about all the gray in between.