Dean Martin had just as many mafia ties as his more well-known mob-affiliated Rat Pack pal Frank Sinatra. Portions of Martin’s FBI file detail his early underworld connections as a gopher, blackjack dealer, dice man and aspiring boxer under the auspice of the mafia in Steubenville, Ohio in the 1930s. Michigan State Police records from the 1970s highlight Martin’s friendly relationship with leaders of a number of Midwest mob families.

Born Dino Crostini in smoggy Steubenville, an ethnically-diverse factory town located on the Ohio River bordering West Virginia, Martin began running errands for local mob boss Jimmy Tripodi and his second-in-charge Cosmo Quattrone at a young age and worked as a stock boy at Tripodi’s Star Cigar Shop, which doubled as a backdoor casino. After he hung up his gloves and gave up his dreams of glory as a prize fighter but before he found his calling as a brilliant, velvet-voiced singer and performer in the entertainment industry, he was employed as a card dealer and stick man at Quattrone’s backdoor casino ran out of his Rex Cigar Shop and after that in Youngstown, Ohio’s infamous Jungle Inn gambling den owned by future Cleveland Godfather James (Jack White) Licavoli.

Latter in life, Martin would recall stories of stealing from customers at Quattrone’s games held at “The Rex,” and how Licavoli and other Youngstown Mafiosi helped land him early gigs singing in nightclubs around the Mahoning Valley. At that time, Licavoli looked after the “Valley” for mob superiors in Cleveland and Detroit.

Jimmy Tripodi lorded over the Steubenville underworld from the end of Prohibition until he retired in the late 1970s. His arrest record dated back to 1920s where he made his name on the streets as a bootlegger and prolific mob killer. He was acquitted of the Dominic Spinetti slaying in state court in 1936 and arrested but never put on trial for the Jimmy Fratini hit in Ohio and the Diego Delisa murder in West Virginia. His most significant conviction was a federal gun charge he did three years in prison for.

The Steubenville mob was a wing of the Cleveland mafia. Throughout the 1950s and 1960s, FBI surveillance teams followed Tripodi and Quattrone to Cleveland to meet with and deliver tribute to longtime Cleveland mafia consigliere Anthony (Tony the Old Man) Milano at Milano’s Italian American Brotherhood Social Club. Per FBI documents from 1967, Tripodi also maintained close links to the Pittsburgh mob via Steel Town crime family capo Antonio Ripepi and the New York mafia through Genovese crime family power Rocco Pellegrino.

While Tripodi headquartered his activities out of The Venetian Italian Restaurant, Quattrone based his affairs out of a bar and supper club known as The Baron. Martin could be seen at both establishments holding court during his trips home in the Rat Pack period, his FBI file notes. The Midway, a restaurant, lounge and backdoor casino owned by Tripodi and Quattrone, often made it into Martin’s rounds on visits back to Steubenville, too.

After a renegade Cleveland mob crew robbed the Baron in 1956, Quattrone got permission to take vengeance, according to FBI records, and put out open murder contracts on the heads of the crew’s two leaders, Dom Marfici and Vince Innocenzi. Marfici, who was the son-in-law of Tony Milano’s driver and bodyguard, was killed in hiding in Buffalo in 1957 and Innocenzi was found dead in a ditch in Canton, Ohio shot in the back of the head in summer of 1960.

Martin played golf and hobnobbed with several members of the rustbelt mob elite in his heyday, including Chicago dons Tony (The Big Tuna) Accardo and Sam (Momo) Giancana, Detroit mafia princes Anthony (Tony Z) Zerilli and Giacomo (Black Jack) Tocco, Ohio crime chiefs “Jack White” Licavoli and Angelo (Big Ange) Lonardo and Pittsburgh gangland legends John LaRocca, Mike Genovese and Kelly Mannarino, according to Michigan State Police documents from 1975. Sinatra, an east coaster, had nothing on his buddy “Dean-O” in America’s heartland when it came to connections to notorious hoods.

One informant told the MSP that Martin hosted Zerilli, Tocco, Accardo and Giancana on the Las Vegas set of the original Ocean’s 11 film in late 1959. An MSP internal memo from 1976 lists an account by two FBI agents who followed Martin from Las Vegas to Illinois to visit Giancana in the hospital after a surgery he had in 1963 and then off to Detroit to play a gig and party with Zerilli and Tocco. Multiple MSP informants relayed to their respective handlers in the government stories of Martin’s appearances at horse race tracks owned by Zerilli and Tocco in suburban Detroit and Wheeling, West Virginia. FBI agents tracked Zerilli and Tocco to a Martin performance in the Pittsburgh area in 1966 and observed the pair of Motor City mob czars dine and play a round of golf alongside Martin and local mafia kingpins Genovese and Mannarino the next day before heading back to Michigan.

Jimmy Tripodi died peacefully in 1987 at the age of 88. Cosmo Quattrone did the same in 1986 at 85. Stricken with lung cancer, Martin passed away on Christmas Day 1995 at his Beverly Hills, California estate, having carved out an iconic legacy for himself as a singer, actor, comedian and variety-show host. US Route 7 in Steubenville was officially renamed Dean Martin Boulevard.

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