Image via AP.

Barbara Sinatra, philanthropist and the widow of Frank Sinatra, has died at 90 in her home in California.

CNN reports that Sinatra died of natural causes, according to the director of her charity, the Barbara Sinatra Children’s Center. The center was founded by Barbara and Frank Sinatra in 1986, and was established to aid “abused, neglected, and at risk children.” In March, KESQ reported that the Center had raised $250,000 in conjunction with Children’s Hospital Los Angeles.

Before marrying Frank Sinatra, Barbara Sinatra worked as a model and Las Vegas showgirl. She had one son, Robert Marx, with a far less successful lounge singer named Bob Oliver. The Desert Sun reports that Nat King Cole played piano at their wedding. They divorced, and her son eventually adopted the name of her second husband, Zeppo Marx of the Marx Brothers.

Barbara met Frank when he was living next door to the married couple, and they became friends during the tail end of his tempestuous relationship with Ava Gardner, even playing couple’s tennis together. Though they knew each other for some time before things became romantic, the change was sudden and took place while Barbara was still married. They remained together until the end of Frank Sinatra’s life, the longest marriage he had, according to The Desert Sun:

“I’ve tried to analyze it,” Barbara told The Desert Sun. “I think it’s because we were friends before anything romantic happened. He would call and chat, but it wasn’t romantic until later. It’s something you can’t explain why or how it happened.”

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Frank’s mother, Dolly, supposedly disapproved of the relationship, not understanding why he would pursue his close friend’s wife. Zeppo and Barbara had a difficult divorce in 1973, which includes this incredible Hollywood anecdote:

Zeppo’s attorney, Greg Bautzer, saw Barbara at a restaurant and viciously told her, “The only thing you’re going to get from Zeppo is the clap.” But, sitting with Barbara were Bee Korshak, a friend from the Racquet Club, and her husband, Sidney, a mob lawyer the New York Times called “one of Hollywood’s most fabled and influential fixers.”

Barbara’s 2011 autobiography Lady Blue Eyes: My Life with Frank shares many such interesting details about her grand romance and wild life in show business.

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In a statement, her foundation wrote, “Through Barbara Sinatra’s efforts, more than 20,000 children through age 18 have received beneficial therapy at [the center], making it possible for them to cope with traumas associated with abuse.”