Saving Ray Charles

Ed Masterman and Paul Redmond convinced a Boston judge to send the music legend to drug rehabilitation instead of prison

Published in 2005 Massachusetts Super Lawyers magazine

By Hank Bordowitz on October 21, 2005


Ed Masterman and Paul Redmond may not have received the face time of, say, The Raelettes, but they played a crucial role in the movie Ray. They are mentioned in a scene toward the end of the film. Federal marshals have arrested the legendary musician for possession of heroin and a judge is giving him the option to break his addiction in a locked ward close to his Los Angeles home. A hospital-gowned Charles sits with the physician overseeing his treatment, Dr. Hacker.

“[The judge] was impressed with your attorneys’ arguments,” Hacker says. “He believes you deserve one more chance. But you must complete our program and take periodic drug tests.” Charles does just that, recovers, and the rest, thanks to Masterman and Redmond, is music history.

“Now that the movie is out,” Masterman smiles, “when they talk about ‘the lawyers,’ my wife tells everybody, ‘He was one of them.’”

Masterman looks magisterial, standing a lanky 6 feet 5 inches with white hair. He has practiced law in Massachusetts since 1951. For the most part, his practice has dealt with property issues. “I am considered an expert in the field of land and its valuation, real estate generally,” Masterman says as we sit in his office at Masterman, Culbert & Tully on Boston Harbor, a marina of brightly colored boats visible out his window. “I helped rewrite the zoning code of the city of Boston.”

Not exactly the first-call attorney for a federal drug possession case. But that’s what he found himself handling on Halloween 1964, when federal marshals arrested Charles for possession of heroin as he landed at Boston’s Logan airport. That evening, Miles Lourie, Charles’ attorney, called Masterman on the recommendation of one of Masterman’s former associates.

“[Lourie] said, ‘Your name was given to me in regards to a lawsuit,’” Masterman recalls.

“I said, ‘Okay, who is [the client]?’

“He said, ‘Ray Charles. Can you handle the case?’ “I said, ‘I’m not really a criminal defense lawyer, but we have an associate here who’s just out of the U.S. Attorney’s office and knows all the procedures.’”

Enter Paul Redmond. He didn’t know who Charles was at the time, but at 4 in the morning on the first day of November he was at the federal marshal’s office bailing out the singer. Thus began the vigorous and imaginative defense of Charles against drug charges, the third time the singer had faced them. (He had previous arrests in Philadelphia in 1958 and in Indianapolis in 1960, but the charges didn’t hold up either time.)

In court, Redmond — who passed away shortly after this interview — took the lead. He was well versed in the procedures and the judges of the local federal courts and worked diligently to orchestrate a strategy to keep Charles out of the penitentiary.

The allegations were serious. “The charges against Ray were really outrageous because he was arrested with a large amount of heroin,” Redmond says. “He had a couple of duffel bags full. They wanted to say that he was distributing. He was really in trouble.”

Meeting the singer for the first time was unforgettable. Charles came to the 73 Tremont St. offices of Masterman and Redmond’s firm with Lourie and his manager, Joe Adams. “He comes in and he was slapping himself,” Masterman says, describing a classic behavior of heroin addicts. “He says, ‘Get me a Coke and some Kool cigarettes.’ So we sent some people out. We talked about the case.

“I tell Ray, ‘I know you. I know you’re pretty famous, but I don’t know your music well. Could you send me some records?’”

Masterman now proudly displays these records in his office. The LP jackets show signs of age and use, but they are still in good condition. The albums include the groundbreaking Modern Sounds in Country and Western Music, Greatest Hits, Have a Smile With Me, A Portrait of Ray and Sweet and Sour Tears, one of the first “concept” albums ever recorded. “I play his records all the time here.”

The first thing Masterman and Redmond had to do in their case was convince the judge that the drugs were for the personal use of Ray and his band. They explained that several members had serious heroin habits and Charles’ own addiction ranged over the course of two decades. The court ultimately accepted this explanation and the harshest of the charges were dropped.

Next came the task of keeping Ray out of prison. The charges against him had a mandatory five-year stretch in a federal lockup. “There was a place in Lexington, Kentucky, a drug rehabilitation center,” recalls jazz legend Sonny Rollins, who spent some time there before “getting pure” in 1955. “It was a federal facility. … A lot of guys who were using drugs during that period seemed to end up in Lexington.”

While people who wanted to take the cure on the government’s dime could check themselves into Lexington — as Rollins did — Charles faced actual hard time there. It would have effectively ended his career, or substantially stalled it, a potential disaster for Charles and popular music in general.

“You have a very tough case,” Masterman remembers telling Charles when they met in his office. “Let’s find a way to persuade the court that you should not be sent to Lexington, that we could save the government a lot of money. But we have to find a place that is a locked ward with all the protection and treatment the government would have, but you would pay for it. You can afford it.”

So Masterman took a trip to his client’s hometown of Los Angeles. There, he visited Tangerine Records, Charles’ company — a pioneer custom label distributed by ABC Records, a major company at the time. “It was very impressive,” Masterman recollects. “A large studio, lots of people. If I remember right, he had a couple of hundred employees.”

Masterman next called a classmate of his, James Roland, the secretary to Massachusetts Congressman Tip O’Neill. Through O’Neill and Roland, Masterman found a contact in the federal marshal’s office in Los Angeles who helped him find a locked ward, run by a noted local psychiatrist, Dr. Hacker.

“So I see Dr. Hacker,” Masterman says. “A big, tall, husky, wonderful guy. He says, ‘OK, this is what we do. We have a hospital in the suburbs of Los Angeles. We take people who have drug problems and put them there.’

“We go out to the hospital, check out the facilities and, sure enough, they have a locked ward. Very small rooms, fully equipped hospital and a locked ward.”

They brought all this before Chief Judge George C. Sweeny of the Massachusetts Federal Court. Redmond argued the significance of Charles’ contribution to the arts and culture of the country. He told the court they had found a suitable locked ward, a doctor and a hospital. They proposed that Charles commit himself to the hospital and get free of his addiction to the satisfaction first of his doctor and then of the court. Sweeny accepted the proposal and ruled that Charles needed to spend a year in the locked ward, at which time he would submit to testing and appear before the court. If he could prove that he beat the addiction, the court would consider putting him on probation with a fine.

“Ray goes to the coast and checks into the hospital,” Masterman says. “I go out to visit him there during the next nine months. He’s staying in a small cubicle. He’s not very happy, but he needs to go through the cure. He’s not slapping himself anymore, he’s just working on kicking his addiction.

“A year goes by. I get a letter from the court ordering us to report. We make arrangements for Dr. Hacker, Joe Adams and Ray. There’s no question to any of us that he has beat the habit.”

But now Charles and his team are faced with a new obstacle. During the course of the year Charles spent in the hospital, Judge Sweeny died. The case got passed along to another jurist, the Hon. Charles Wyzanski, one of the strictest and most admired judges on the federal bench. “We all, if not revered him, respected him enormously,” says Masterman, while adding, “He was very smug. … He was a piece of work.”

“I knew Charlie very well,” adds Redmond, who had spent a lot of time in the judge’s court as a federal prosecutor. “I feared not from Charlie.”

This made Redmond one of the few people practicing in the federal court in Boston who could say that. “Wyzanski’s court clerk, Charlie Duffy, used to say, ‘You’re the only guy who plays Charlie like a violin,’” Redmond laughs. “He used to treat me beautifully.”

Redmond faced Judge Wyzanski and told him that Ray Charles had lived up to his part of the deal. He had tested negative for drugs, had beaten his addiction. But the judge shook his head. “The statute is clear,” he said. “This is mandatory. He’s got to go to jail.”

“At this point,” Masterman recalls, “Ray Charles is about to collapse. I’m about to collapse. Paul says to me, ‘We’re in trouble!’ And Hacker and Joe Adams and the U.S. Attorney are all nonplussed because we had come to this deal.”

Then Wyzanski’s clerk approached the judge. The clerk handed a letter to Wyzanski — he looked at it, read it and then held it up, Redmond recalls. “He opened the envelope and said, ‘Mr. Redmond, I have a letter here from Chief Judge Sweeny. It may be of interest to you. What we have here, gentlemen, is a letter from the grave.’”

It turns out that before he died Judge Sweeny had written a memorandum as to how he agreed to rule. Judge Sweeny apparently gave the memorandum to his clerk, who handed it over to Wyzanski’s clerk. Judge Sweeny’s terms were for two years of probation and a $10,000 fine. Wyzanski took this recommendation and added two years to the probation.

“It was a letter from the dead!” Masterman says in amazement 40 years later. “Who could imagine that a judge could be that thoughtful, knowing he’s going to die, to leave that?”

“I do not claim credit for the wisdom of this sentence,” Judge Wyzanski would tell a law school audience at the University of Georgia nearly a decade later, “It is the wisdom of my predecessor as chief judge, George C. Sweeny, whose path I have followed.”

And that is how this memorable and historic case ended for Masterman and Redmond. “I’ve been a lawyer a long time,” Masterman says in reflection, “and people always ask whether I have any cases that really stand out. I tell them, I have a couple. This is one of them.”

Search attorney feature articles

Other featured articles

Stuart Singer fought a 17-year battle to guarantee health care for Florida’s poorest children

The language used in the initial ruling, they say, is disturbing and troubling

Jay and Leah Edelstein carry on the tradition of Nathan and Edward

View more articles featuring lawyers

Find top lawyers with confidence

The Super Lawyers patented selection process is peer influenced and research driven, selecting the top 5% of attorneys to the Super Lawyers lists each year. We know lawyers and make it easy to connect with them.

Find a lawyer near you