How Leon Charney Outsmarted Sinatra

In 1976 New York Post gossip columnist Earl Wilson was running scared. His tell-all book, “Sinatra: An Unauthorized Biography,” enraged Ol’ Blue Eyes. No surprise there. The volatile crooner, known for his combativeness with photographers and reporters, called the book “false, fictionalized, boring and uninteresting” and instructed his lawyer to sue Wilson for $3 million.

Earl was in shock. He had considered himself part of Sinatra’s world, a professional fan, always boosting him in his widely syndicated column. Now he was crying, “I need a lawyer!”

Being his resourceful assistant, I offered to call a personal friend Leon Charney, a confidant to many Hollywood stars and Washington insiders.

Leon formed a strategy whereby he had the right to take Sinatra’s deposition. “My feeling,” he told me, “was that Sinatra would not make himself available for a deposition because, in a sense, we could ask the same questions he was suing Wilson on. He was saying that Wilson made statements that were not true. I would ask him what is the truth. I would ask whether he was in love with Ava Gardner or not, plus questions concerning his relationship with Juliet Prowse and Mia Farrow. I had my doubts that he would sit for such an interview. His answers would cause a media sensation.”

Leon flew to Los Angeles to meet the singer’s lawyer, the invincible and fearsome Mickey Rudin. They rode in Rudin’s Rolls Royce to Sinatra’s home in Palm Springs.

On the way he kept wondering if his strategy was going to work. “Rudin sounded like a teamster from Hoboken,” Leon said. “He kept a cigar in his mouth. I told him I hate cigar smoke and could he please put it out. He glared at me. It’s his car and who am I to tell him what to do. But he put down the cigar.”

At that moment Leon knew he had won the case. “Because,” he said, “if Rudin did not really want to accommodate me, he would have dropped me in the middle of the desert and tell me to take a cab.”

Sinatra settled. “The settlement is secret,” Leon said, “but all agreed that the beneficiary would be Hebrew University.”

A year later, Leon served as best man at my wedding with Nina. As attorney for the Concord Hotel, he arranged for me and my bride to celebrate many a Passover seder in the Catskills.

The real estate billionaire, attorney, author and philanthropist (who founded the Leon H. Charney School of Marine Sciences at the University of Haifa), died in Manhattan on March 21 at age 77, leaving his wife Tzili, a former costume designer from Israel, and twin sons, Mickey and Nati.

Tim Boxer was a columnist at the New York Post for two decades. At the same time he has been a columnist for The New York Jewish Week for 36 years, and editor of for 17 years. He is the author of Jewish Celebrity Hall of Fame, interviews of Hollywood stars about their Jewish roots, from which this story was adapted.

About the Author
Tim Boxer is a former New York Post columnist, and is longtime columnist for the New York Jewish Week. He is also editor of, is the author of Jewish Celebrity Hall of Fame, interviews of Hollywood stars about their Jewish roots.