It’s been over twenty years since the iconic singer Frank Sinatra passed away, but he is still missed by millions of fans to this day. Now, his friend and former manager Tony Oppedisano is speaking out to reveal new details about Sinatra’s life.

“Most people would think he would say his greatest accomplishment was one of his huge records like ‘My Way,’” Oppedisano told Closer Weekly. “But I think [he’d say] his greatest accomplishment was trying to … help as many people as he possibly could, whether he knew them or not.

Oppedisano spent decades working for Sinatra, and he learned a lot about him during that time.

“He taught me some of the greatest life lessons,” he said. “He was like a second father to me.”

Oppedisano went on to add that Sinatra would help his friends out “emotionally and financially,” even going so far as to pay for life-saving surgeries for them.

Many fans would be surprised to learn that Sinatra was someone who could not stand conflict.

“As tough a guy as he was — and God bless him, he grew up in a tough neighborhood — when he got into any kind of conflict with someone he cared deeply about, like his kids or [his fourth wife] Barbara, he would almost become a little kid and try to make the world go away,” Oppedisano recalled. “He didn’t like to argue with people he loved.”

Oppedisano also said that Sinatra never got over the pain that he caused his first wife Nancy when he left her for the Hollywood star Ava Gardner.

“We were on a flight overseas once, and everyone on the plane was asleep,” Oppedisano recalled. “He was talking about the night he won the Academy Award for From Here to Eternity and how, when he went back to the house, Mrs. Nancy had organized a gathering for him. He … felt overwhelmed, and he rushed out. He regretted that.”

In the end, Sinatra was a sensitive soul until the day that he died in 1998. Oppedisano concluded his interview by saying, “I miss him as much as my own father.”

Rest in peace, Frank Sinatra.