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:

It’s hard to say whether Sinatra should be criticised, or not, for landing a sock on the jaw of columnist Lee Mortimer in Ciro’s. Even if the sock also landed him in the headlines again–and almost in the hoosegow!

It seems that Mortimer allegedly murmured a slurring remark as he passed Frank. Apparently the remark did no credit to minority groups — reflecting on the nationality to which Frank belongs. The Italians.

Anyhow, Frankie’s bellicose nature — which he had kept under remarkable restraint since his stormy, fight-ridden Tommy Dorsey days — asserted itself. He let go with a wallop. He ended up in Court, finally settled privately the assault and battery charges brought against him by Mortimer. But there was no settling the unfavorable glare of his name spread out again on the front pages of the nation’s newspapers.

With the Mortimer mess, though, Frankie’s hard luck year came to an end. That is, as far as gossip and scandal. But the stress and strain of publicity and the notoriety had apparently taken its toll.

Sinatra in the Beverly Hills courthouse after his arrest for slugging Lee Mortimer at Ciro's

The slurr was “Dago,” but that was not the only shot Mortimer took at Sinatra. According to Anthony Fiato at Hollywood Goodfella, Mortimer also accused Sinatra of having ties to a well-known mob figure in Los Angeles:

The mobster in question was my Mafia cohort, Johnny Roselli. Mob boss Sam Giancana told Sinatra to consider Roselli his eyes and ears. Sinatra was one of the sponsors for Johnny’s membership in the Friars Club.

Lee Mortimer, Sinatra’s sluggee, wrote for The New York Daily Mirror, a Hearst paper. He was also the author, with Jack Lait, of New York: Confidential!, a bestselling guide to underground places and activities in post-war Big Apple. Other than hating on Italians, it’s unclear what Mortimer’s beef with Sinatra was.

When the FBI released its files on Sinatra not long after he died in May 1998, researchers found an item that indicated that that Mortimer had a conversation about Sinatra with Clyde Tolson, the very close associate (many say life partner) of FBI Director J. Edgar Hoover, a few months after the incident at Ciro’s. According to researchers who examined the files “Tolson steered Mortimer to the right place for information on Sinatra’s 1938 arrest on seduction charges, involving an affair with a married woman. Mortimer turned over a picture of Sinatra and another man, taken in Cuba, in hopes the FBI could identify the man as a mobster.”

Among the documents in Sinatra’s file was a mug shot taken in 1938 after he’d been arrested on a charge of seduction in Bergen County, N.J. The charge was later dropped.