When Eliot Weisman became Frank Sinatra’s manager in 1975, he was warned by his friends in show business that he didn’t know what he was getting himself into. But Weisman said yes to the job offer and became a close confidant, oftentimes acting as a therapist, until the singer’s death in 1998.
Weisman recently shared his accounts of what it was really like working with the iconic entertainer in a memoir titled “The Way It Was.”
The former manager told Fox News that when he met Sinatra, he didn’t see a suave, debonair crooner who casually kicked back with a glass of Jack Daniel’s. Instead, he witnessed an aging performer who was worried about the future.
“He was at the crossroads of the pressure he was receiving for his wife, his security and his children regarding the assets of his estate,” Weisman told Fox News. “They had started a couple of little businesses, none of which had really worked out… It was uncomfortable. Because I was the monkey in the middle… It started to make sense 2-3 years down the line.”
Sinatra was also reportedly paranoid about his safety. Not only did he carry an Uzi on his private jet, but he also kept a pistol hidden in his custom boots while on stage at all times, Weisman said.
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