A post shared by Azura🌹 (@azura_deceiver) on Nov 7, 2017 at 7:10pm PST

Frank Sinatra’s manager, Eliot Weisman, was with the star from 1975 to his death in 1998.

In a new memoir called The Way It Was, the manager opens up in more detail about his relationship with Frank.

Eliot told Fox News that Frank was incredibly worried about his 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,” Eliot said. “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.”

“A lot of these habits were going on for years and I wasn’t even totally aware of them until I was told about them,” he admitted. “… I guess it’s something that never really bothered me because I knew that… he always had security around him. So if God forbid something really happened, he wouldn’t be anywhere near it. But I wasn’t worried about it.”

The effects of the drugs became so severe that Frank started struggling remembering lyrics.

“If you read about the antidepressant he was on, if you read the warnings, everything that could go wrong, like loss of vision, loss of hearing, loss of memory — all of those things he at one time or another was harmed by it,” he explained. “The antidepressant he was on… I think you’re only supposed to be on it for 12-13 months, at most. Then you come off it for a while or change it to another antidepressant. He was on it for 10-15 years.”