Life With Ol’ Blue Eyes

Eliot Weisman has lived a life many would likely envy.

For over 20 years, he was Frank Sinatra’s manager, serving as the music icon’s right-hand man for just about everything, including being executor of Sinatra’s will when he died in 1998. 

Traveling the world with whom the entertainment industry dubbed the “Chairman of the Board,” Weisman often found himself in the company of other incredibly famous artists like Liza Minnelli and Sammy Davis Jr. — people who could intimidate many unknowingly just by being in their presence.

But when most high-profile people were around Sinatra, he was the one who made people nervous.

“I saw dignitaries say hello to him backstage whose knees buckled,” Weisman says, adding that he never called Sinatra by his first name. Instead, he affectionately referred to him as “Boss” or “Mr. S.”

Sinatra liked to read the local newspaper in the towns he performed in and if he saw a story about a firefighter in need he would tell Weisman to give them $5,000. Sinatra always had a soft spot for helping others, even as his fame exploded, because his father was a firefighter.

“He did that many times. He was the champion of the underdog,” says Weisman, a Brooklyn native who lives in Parkland with his wife, Maria. “I loved him for that.”

Just two years ago, Weisman put pen to paper and highlighted some of his greatest memories in a book called “The Way It Was: My Life with Frank Sinatra,” which he co-wrote with South Florida TV journalist Jennifer Valoppi. 

In it he writes about his greatest career accomplishment — helping to create two “Duets” albums in the early 1990s where Sinatra performed some of his favorites songs with other iconic artists like Barbra Streisand and Aretha Franklin. “Duets” helped reinvent Sinatra and ended up being the two biggest selling albums of Sinatra’s career.

“He made the industry what it is today, it’s all built off of him,” Weisman says. “Sinatra was the entertainer of the 20th century.”

And how fortunate Weisman was to have had a front row seat to it all.