Meet Frank Sinatra's right-hand man at Ruth Eckerd Hall

Published November 29 2017

For 17 years, Eliot Weisman did things Frank Sinatra’s way.

Weisman was the Chairman of the Board’s manager and confidant during Sinatra’s last hurrahs, first gaining the legend’s ear by keeping his mouth shut.

In 1981, Weisman left federal prison after serving time for racketeering charges connected to his theater, where Sinatra often performed. Investigators were intrigued by a photo of Sinatra and Weisman surrounded by organized crime bosses.

Pressed to snitch on the singer’s mob ties, Weisman continually refused. Sinatra rewarded him with the job of a lifetime.

"He was so true blue he was predictable," Weisman recently said from his Coral Springs home. "If you knew him as well as I did, you know what his moves were going to be."

Sinatra’s later-year moves are detailed in Weisman’s biography The Way It Was: My Life With Frank Sinatra, co-authored with Jennifer Valoppi. Weisman will talk about his time with Sinatra at Celebrating Sinatra on Dec. 10 at Ruth Eckerd Hall.

The book is a name-dropper’s delight, from backstage memories of Sinatra’s aborted reunion tour with Dean Martin and Sammy Davis Jr. to falling out with Don Rickles. Weisman’s additional clients — first-namers like Liza and Steve and Eydie — sweeten the mix.

Weisman, 79, also profiles Sinatra in declining health and confidence. He was racked by depression and overmedication, yet still able to pull off a triumph or two, like 1993’s Duets album that his wife, Barbara, goaded him into recording.

One track paired Sinatra with someone he’d never heard of. Weisman details how the crooner and U2’s Bono became fast friends.

The Way It Was is a nostalgia trip that nearly didn’t get booked. Publishers didn’t jump at the idea of a Sinatra biography without the "juicy stuff" of his earlier years: two movie star marriages gone sour, intimate relationships with the likes of Marilyn Monroe and Angie Dickinson.

"We went to New York and met with a publisher, a pretty crowded room," Weisman said. "They told us, ‘Wow, this outline looks great … but what about the women?’

"I told him, ‘Listen, I didn’t start until 1977 and the boss got married in 1976. The reality is that I never saw him with another woman except for Jacqueline Kennedy, who he had dinner with. And that was three or four years before he got married.’"

The publisher persisted, wanting information Weisman didn’t know. "You may not have lived all those stories, but you sure as hell know them," are what he recalls hearing.

He sounded like a federal investigator digging for dirt. Weisman was ready.

"I told him, ‘I don’t believe anything I hear and half of what I see and this meeting is over,’" he said. "Jennifer and I walked out. I wasn’t about to write a researched book or a hearsay book. … I wouldn’t have any part of it."

Still being a standup guy for the man Weisman knew only as Boss or Mr. S.

A few years passed. Weisman shared his illustrious story in conversations, occasionally with teenage friends of his children who were "fascinated" to his surprise. His daughter urged him to take up the book project again. He agreed on one condition.

"I told her, ‘Okay, you’re a royal pain in the a--,’" he said. "‘If you go get me a deal, I’ll do it. Not self-published. Get me a guarantee and I’ll do it.’ Two months later, she had a deal. I said, ‘Wow, I guess I’m stuck.’"

Weisman’s last chapters describe Sinatra’s death in 1998 and years of litigating his estate as executor of the entertainer’s will. It’s a messy, complex affair that bitterly divided Sinatra’s immediate family and former wives. Most are gone now after Frank Jr. died in 2016. Only Sinatra’s daughters, Nancy and Tina, survive.

Weisman mailed them copies of The Way It Was. He never expected a reply.

"Tina is a litigious human being who thinks she’s Frank Sinatra Sr. sometimes," he said. "She and I did not part ways very well. I didn’t care then nor do I care now."

Contact Steve Persall at [email protected] or (727) 893-8365. Follow @StevePersall.

If you go

Celebrating Sinatra

The event at 7 p.m. Dec. 10 includes video clips and anecdotes of Sinatra’s life as well as a Q&A with Eliot Weisman. Murray Theatre at Ruth Eckerd Hall, 1111 N McMullen Booth Road, Clearwater. $35, includes a signed copy of Weisman’s book . (727) 791-7400.

The Way It Was: My Life With Frank Sinatra
By Eliot Weisman
Hachette Books, 328 pages, $27