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

He subpoenaed George H.W. Bush. He negotiated the book deal that became Goodfellas. He won drug cases the federal government thought were slam dunks. And then Robert Simels became the one sitting at the defense table.

I just got off a call with one of the most legendary criminal defense attorneys in New York history, and I have to tell you - this one hit different. Robert Simels wasn’t some guy who made a bad decision and ended up in the system. He was the guy who beat the system, over and over, for 35 years. Then he got a 14-year sentence.

From Prosecutor to Perry Mason

Robert grew up in Westchester County outside New York City. His dad was a dentist. He thought he’d play baseball for the Yankees. But his mother convinced him there was more money in law than in the $5,000 signing bonuses they offered college players back then.

“At nine years old, a relative gave me a book on jurisprudence,” Robert told me. “I read it. He came back and tested me on what I learned.”

Nine years old. Reading law books. The kid was built for this.

He started as a prosecutor with an elite anti-corruption office in New York City in the 70s. They were going after crooked cops, dirty judges, corrupt politicians. The kind of work that makes enemies.

“We indicted 11 judges. We indicted the state Democratic chairman. We were very active people,” he said.

Then a new governor came in and shut them down. But the people they investigated? They never forgot.

The Goodfellas Connection

Here’s a story Robert told me that blew my mind. It’s Memorial Day weekend, 1980. He’s in his office at 4:15 in the afternoon - probably the only lawyer in New York not in the Hamptons.

The phone rings. A federal judge needs him to witness someone signing a document in Brooklyn. That someone was Henry Hill.

You know Henry Hill. The mobster. The guy Ray Liotta played in Goodfellas.

The prosecutors wanted Henry to plead guilty to a few crimes before entering witness protection. Robert walked in, talked to the guy, walked back out and said no deal.

“I said he’s not pleading guilty to anything. They said you’ll undercut our cases. I said I don’t really care.”

That’s Robert Simels in a nutshell. He got Henry into witness protection without any plea. Then he spent a year and a half shopping Henry’s story around New York and Hollywood.

“I went to the head of Simon & Schuster. The head editor said we don’t do Mafia stories, we’re never doing this book. Then Dick Snider came barging through the door. I told him my concept. He said this is the greatest story I ever heard.”

That book became Wise Guy. That book became Goodfellas. Robert was on set during filming. He watched De Niro and Pesci ask Henry questions 25 times a day even though Scorsese told the actors not to talk to him.

Taking on the President

But the case that really showed who Robert Simels was? Christopher Drogoul.

Drogoul was a banker in Atlanta who loaned billions of dollars to Saddam Hussein. The government said he did it all on his own, that the US didn’t know anything about it. Robert didn’t buy it.

“Deep within the CIA, people started coming to me,” Robert said. “The deputy director of the CIA called me up and said you’re going about your defense all wrong. Meet me.”

So Robert met this guy in the St. Regis ballroom. Empty room. Single figure sitting in the middle. Dust coming through the sun rays. Like a scene from a movie.

The CIA guy told Robert exactly what to write in a court filing that would scare the government. Robert wrote it. The government immediately dropped 180 of the 347 counts.

Then Robert did something nobody does. He subpoenaed the President of the United States.

“I subpoenaed George Herbert Walker Bush. The Secretary of State Jim Baker. National Security Adviser Brent Scowcroft. Henry Kissinger.”

Kissinger called him personally. “Do you know who you’re talking to? Do you know who you subpoenaed?”

The 11th Circuit agreed Robert could subpoena the President. Then Clinton came in, Janet Reno became Attorney General, and she called Robert directly. They offered Drogoul six months instead of life. The trial was six months away. He’d be done with his sentence before it even started.

When the Hunter Becomes the Hunted

The more Robert won, the more the government hated him. They subpoenaed him repeatedly. They claimed he was unethical. They couldn’t understand how he kept winning unless he was doing something wrong.

“My colleagues would go into court, shake the prosecutor’s hand, go to lunch with them,” Robert said. “I did none of that. It was war. Because to lose meant my clients could go away forever.”

Then came Roger Khan. A drug kingpin from Guyana. Robert took the case and went to Guyana to gather evidence. The US Ambassador was in the same hotel lobby watching him hold a press conference.

The prosecutors asked the judge to throw Robert off the case. The judge said no, but told him to knock it off.

Then a man approached Robert claiming he wanted to help. Robert didn’t know the guy was working for the government, scripted to bring up violence. When the man suggested harming a witness’s mother, Robert shot it down immediately.

“I said you can’t kill this guy’s mother. This is not Guyana.”

The government used that against him. Said he only told the informant not to kill that one specific mother. Robert’s response? Why would he mention anyone else’s mother when the informant didn’t bring it up?

When Robert told the informant to bring a witness to his office, nine federal agents showed up instead and arrested him.

14 Years

Robert wanted a speedy trial. His friends told him not to represent himself. Against his better judgment, he hired someone else.

“I’ve regretted that decision ever since.”

The government put up an organizational chart of the drug operation with Robert’s photo at the top alongside his 25-year-old associate. They called him a killer’s friend. They used the fact that one of his client’s associates had the email “SilentAssassin@yahoo.com” against him.

The jury deliberated seven days on a six-day trial. The judge kept them going when he should have declared a mistrial.

When 65 defense attorneys from around the country wrote letters asking for leniency - saying Robert did what prosecutors and defense attorneys say every day - the judge responded: “I’ve read those letters and I am going to show them something today.”

He sentenced Robert to 14 years. More time than he gave the actual drug dealer.

Prison

Robert did time in Big Spring, Texas. Safford, Arizona. Allenwood, Pennsylvania. Danbury, Connecticut.

At Big Spring, they said nobody would know who he was. Within three days, an interview about one of his clients aired on TV and everyone knew.

“The third day I was in prison, there was a show about one of my clients. I said well anybody who didn’t know who I was, they know now.”

His reputation preceded him everywhere. At Safford, when the white inmates told him he had to sit with them in the dining hall, Robert went to the black inmates he’d connected with during transport. They talked to their leadership. He sat with them instead.

“In the dining hall there was a sea of black on one part, and one white face. There was Robert.”

He walked. He read over 3,500 books. He worked out at 6 AM when nobody else wanted the equipment. He kept to himself.

Family

Here’s what gets me about Robert’s story. His family stayed.

His son was seven when he got arrested. The other kids at school told him his father would never come home. His daughter was fifteen and going through the same thing.

“That more than anything else breaks your heart. What you do to your family.”

His wife Evelyn flew to every prison. Houston to Midland then three hours to Big Spring. Phoenix then three and a half hours through mountain roads to Safford.

The guards would tell her she couldn’t come in because of what she was wearing. They’d say Robert was out of points when he wasn’t. They’d cut visits short for no reason.

“There aren’t words to describe what they did for me,” Robert said about his family.

Getting Out

Robert was over 70 when the First Step Act passed. His case manager didn’t even know how the early release provision worked. Robert helped him fill out the paperwork.

On November 4, 2019, the warden told him he was going home. First person released under that program at his facility.

But prison cuts your phones and email the day before you leave. He had no way to tell his wife.

Two months earlier, he’d told her: come to the prison on November 5th. Maybe it’ll happen, maybe it won’t. They’re not telling me anything.

She showed up. His car was there.

“I looked across, saw her car, raced over, got in, and left. Out of here.”

The System is Broken

Robert now does consulting work. He speaks at Yale Law School and other places. He helps people navigate the federal system as someone who’s been on all three sides - prosecutor, defense attorney, and defendant.

“The system is in shambles,” he told me. “Not the way Mr. Trump says it is. It’s awful because it doesn’t work right. Judges take those black robes and they no longer see you. They just want to sentence you to prison.”

He talks about prosecutors asking for 50 years for Sam Bankman-Fried. “Who learns their lesson in 10 years that doesn’t learn it in one?”

What Robert offers now is something I wish I’d had. Someone who knows the game from every angle. Someone who will listen when your own attorneys won’t.

“Your attorneys really don’t want to hear what you have to say,” he said. “But you know more about the case than I may ever know. Tell me everything. Send me a text, send me an email, call me.”

Robert Simels spent his career fighting for people facing the full weight of the federal government. Then he found out what that weight feels like. He survived 14 years. His family survived it with him.

That’s a nightmare. And he’s still standing.