Frank Sinatra Was a Ringside Photographer for the ‘Fight of the Century’ With Muhammad Ali

In 1971, Frank Sinatra, like many other celebrities, attended the “Fight of the Century” between Joe Frazier and Muhammad Ali. Unlike most celebrity attendees, however, Sinatra had a job to do. Hired by Life Magazine, Sinatra sat ringside to photograph the fight. One of his shots ended up on the cover of the magazine.

Frank Sinatra turned on boxer Floyd Patterson after he lost to Muhammad Ali

Sinatra was not a fan of Ali, evidenced by his previous attempts to see him lose a fight. In 1965, Sinatra did all he could to see boxer Floyd Patterson beat Ali. He even set Patterson up with a trainer. On the day of the fight between Patterson and Ali, Sinatra invited Patterson to see him.

“Sinatra was very nice that morning, very encouraging, he told me I could win, how so many people in America were counting on me to win back the championship from Clay,” Patterson wrote in a 1966 article for Esquire.

Patterson lost the fight in a technical knockout in the 12th round. Afterward, Patterson visited Sinatra.

“I told him I was sorry I had let him down, and all the others, but Sinatra was a very different guy after I lost to Clay,” he wrote. “I was talking to him in his suite and then he did a strange thing. He got up and walked all the way over to the other side of the room, and he sat down there, so far away that I could hardly talk to him. I got the message. I left.”

Frank Sinatra’s photo of Muhammad Ali and Joe Frazier was on the cover of Life Magazine 

Several years later, Sinatra was invested in another Ali fight. He got ringside seats to the “Fight of the Century” between Ali and Joe Frazier and planned on taking pictures. Life Magazine’s managing editor Ralph Graves wanted to take advantage of this.

“Shortly before the fight [staff writer Tommy Thompson] learned that Sinatra had wangled himself a ringside seat and was going to take pictures with a battery of cameras,” he told Vice. “Tommy went to work wangling Sinatra into letting us have a look at his film. We didn’t expect to get anything the professional photographers didn’t have, but it might be worth inspecting.”

Sinatra later shared his experience taking photos ringside.

“I got some good pictures that night, but I kept watching Frazier putting his head too far out for Ali to punch it,” he explained. “He was defying Ali, and I said to the newspaper guy next to me: ‘He may win, but if he keeps that up, he’s going to the hospital, taking all those punches.'”

Though Sinatra was an amateur photographer, his photo ended up on the magazine’s cover.

The singer had other artistic pursuits

Sinatra enjoyed photography, but his favorite artistic pursuit — outside of singing and acting, of course — was painting. He favored an abstract style and would throw himself into the work. His wife Barbara wondered if the activity was therapeutic for him.

“He was, of course, Charlie Neat [as he was dubbed after his obsession with cleanliness – Ed.] when it came to painting; there was rarely any mess,” she said, per Artland. “He only ever had one ‘Jackson Pollock moment’ that I knew of. I walked into his studio one day and found him reaching into pots of paint with his fingers and hurling it at the canvas. I don’t think he even knew I was there. Watching him lost in a world of his own creativity, I knew that art was another kind of therapy for him.”

Though it was just a pastime, one of his paintings sold for $100,000 in the years following his death.