Frank Sinatra wasn’t just the King of the Rat Pack or the man behind those unforgettable songs. He was a complex individual whose life was filled with more than just fame and fortune. Tony Oppedisano, one of his closest friends, offers a glimpse into the softer side of Ol’ Blue Eyes, a side that wasn’t always in the spotlight. Known for his charm and swagger, Sinatra also had a heart that cared deeply for those around him.
A Kinder Side of Sinatra
“Most people think his greatest accomplishment was one of his big hits like ‘My Way,’” Tony tells Closer in an exclusive interview. “But if you really knew him, you’d realize it was his efforts to help people—anyone, whether he knew them or not.” Tony had a front-row seat to Sinatra’s life for decades, and what he saw was a man who went out of his way to assist those in need. From paying for life-saving surgeries to offering emotional support, Sinatra’s kindness often went unnoticed by the public.
From Jazz Musician to Sinatra’s Inner Circle
Tony’s journey with Sinatra began in 1972 when they met through a mutual friend, nightclub owner Jilly Rizzo. At the time, Tony was a jazz musician, but his life changed dramatically when he became part of Sinatra’s management team. Over the years, Tony became one of Sinatra’s most trusted confidants. “He taught me some of the best life lessons,” Tony recalls, adding that Sinatra was like a second father to him. In his new book, Sinatra and Me: In the Wee Small Hours, Tony shares stories and insights from their time together.
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Sinatra as a Father
Despite his larger-than-life persona, Sinatra was deeply committed to being a good father to his children: Nancy, Tina, and Frank Jr. “He made every effort to be the best dad he could,” Tony says. Sinatra’s protective nature wasn’t limited to his family; it extended to his friends and even past loves like Marilyn Monroe. He remained supportive of Mia Farrow long after their relationship ended, offering her a shoulder to cry on whenever she needed it.
Conflict Wasn’t His Thing
One of the most surprising things about Sinatra, according to Tony, was his aversion to conflict. “For as tough as he was, growing up in a rough neighborhood, he hated arguing with people he cared about,” Tony explains. When it came to his family, especially his children or his fourth wife, Barbara, Sinatra would do anything to avoid a confrontation. Instead, he would retreat, almost like a child, hoping the issue would resolve itself. Even years after leaving his first wife, Nancy, for Ava Gardner, Sinatra still carried guilt for the pain he caused her.
During a flight overseas, Sinatra opened up to Tony about a regret he carried for years. “We were on a plane, and everyone was asleep,” Tony remembers. “He started talking about the night he won the Academy Award for From Here to Eternity. When he got home, Nancy had organized a party for him, but he felt overwhelmed and rushed out. He regretted that moment for the rest of his life.”
Sinatra’s sensitivity was a part of him that many didn’t see. “I miss him like I miss my own father,” Tony says, highlighting the profound impact Sinatra had on those who knew him well.
