By the time his career ended, Frank Sinatra had become the avatar of 1960s’ “Rat Pack” cool. An American original. An institution.

His career took off in the early years of World War II when his smooth, mournful crooning thrilled socks off of bobby-soxers. But within a very few years, his career suddenly veered into the weeds.

Part of the problem was that smoking and booze had deepened his voice. Once known as “The Voice,” he was derided as “The Gargle.”

It didn’t help that he kept popping up in the headlines, and not in a good way. In 1946, on a visit to Cuba, Sinatra was seen shaking hands with the mobster, Lucky Luciano. In 1947, he briefly left his wife and children, Nancy, age seven, and Frank Jr., age four, for Lana Turner. His former bobby-soxer fans, now entering their twenties, were appalled.

But at Ciro’s on April 9, 1947, Sinatra caused another uproar when he was arrested after taking a swing at columnist Lee Mortimer.

Here’s how the incident was described Modern Television & Radio in December 1948, by Barry Ulanov, editor of Metronome Magazine:

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