On July 28, 1976, “Handsome Johnny” Rosselli, a mobster who rose up through the ranks with Al Capone, had brunch with his sister in Miami before borrowing her car and driving to the marina. There, he boarded a private boat with two men, one of them an old friend. But when they got out to sea, the third man—someone Rosselli didn't know from Chicago—strangled the 71-year-old gangster to death. He wasn’t even on the vessel an hour and he was dead, rubbed out by a Mafia hitman who sawed off his legs, stuffed his body into a 55-gallon oil drum, and threw the barrel overboard into Dumfoundling Bay.

The barrel didn’t sink, and fishermen found it ten days later lodged on a sand bar in a canal, as the New York Times reported the following February.

It was an ignoble end for Rosselli, a self-styled playboy who acted as the Mafia’s ambassador both in Los Angeles in the 1930s and Las Vegas in the 1950s. A charming racketeer who held company with infamous mafiosos, Hollywood moneymen, stars and starlets, Rosselli even had some encounters with members of Congress before it all unraveled for him in Miami.

In the new book, HANDSOME JOHNNY—The Life and Death of Johnny Rosselli: Gentleman Gangster, Hollywood Producer, CIA Assassin, Lee Server explores the life and times of the man who helped bridge the gap between the movies and the mob. VICE talked to Server to find out how Rosselli made it into the organized crime mold—and how he brought mafia muscle to bear in Hollywood, at least for a while.

VICE: Was there one moment that you suspect kind of set Johnny Rosselli on a course to organized crime?

Lee Server: Rosselli had been drifting across America as a young man. He’d settled in Los Angeles in the 1920s, become a bootlegger, then a gambler and racketeer. A fortuitous encounter brought him to the attention of Al Capone, whose eye for criminal talent was second to no one. He recognized something in Johnny at a time when Capone was in need of a liaison between Chicago and the West Coast. He became a kind of honorary consul for the Chicago Outfit in LA.

I think we all had a vague sense that the mob might have been involved in Hollywood productions, but this wasn't just a question of peripheral dabbling—it went to the top.

Part of Rosselli’s "assignment" in Los Angeles was to cultivate relationships with the film industry hierarchy. He knew everybody, dated movie stars, played golf with studio heads. His closest industry friend was the boss of Columbia Pictures, Harry Cohn. They socialized together, and Johnny was often at the studio advising the mogul on his gangster pictures. When Cohn needed a large loan in a hurry it was Johnny who put him together with East Coast mobster [Abner Zwillman]. This had its own complications, as the mobster maintained his secret piece of Cohn’s studio for many years, until he died suddenly, tortured to death or by his own hand, depending whose story you believe.

Rosselli's meddling eventually spun out of control, right?

He collaborated with Frank Nitti—Capone’s successor in the Chicago mob—on a plot to take down the entire Hollywood movie business. They did this through gaining control of a labor union, and then demanding huge under-the-table payoffs from each studio, threatening to close down all movie production if they didn’t pay. The mobsters made millions. It came undone in the end, and many of the perpetrators ended up in prison.

He did actually co-produce films like He Walked By Night and Canon City later in the 1940s—so his wasn't just a criminal gig. Did you take that as a deliberate choice, to find traditional work?

When Rosselli got out of prison on parole, he had to find legit employment. Most ex-cons usually met this parole requirement by taking day-labor jobs, working as dishwashers or similar. Rosselli being Rosselli, he got a job as an associate producer at a movie studio. He formed a production company with Bryan Foy and produced two noir crime pictures in a row. My research revealed how important Rosselli’s contribution was to developing these two great films.

I was struck by just how many public friendships he had with such big names—it was pretty brazen stuff, even after his stints in prison.

Johnny met Marilyn Monroe through the producer (and felon) Joseph Schenck. They were close for a while, lovers according to some. I could not confirm it, but the rumor was that he helped get Monroe her first prominent part in Ladies of the Chorus at Columbia.

As the virtual godfather of Las Vegas in the 50s and 60s, Rosselli knew most of the big showbiz stars who played the showrooms. Sinatra and Dean Martin were personal friends. They partied together. Frank and Dean sponsored Johnny’s membership in the Friar’s Club.

This guy clearly had a flair for the dramatic. Was there one episode you think captured that?

The Kefauver Hearings in the early 1950s was the first in-depth government investigation of nationwide organized crime. Few people in America knew just how far-reaching was the spread of what was known then as the Mob and the Syndicate, corrupting every area of the country. The Kefauver group from Washington hauled in every top gangster, including Johnny Rosselli. Unlike most of the mobsters, who tried to play it tough and not say anything (and some went to jail for it), Rosselli answered every question, but with a strategic skill that ultimately gave nothing away.

But what got him killed if not his (repeated) Senate testimony?

I’ll echo the words the homicide detective who found his body said to me: he had pissed off a lot of people.

This interview has been lightly edited and condensed for clarity. Learn more about Server's book here.

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