1940s
In 1942, Roselli was indicted on federal labor racketeering charges along with George Brown, former president of the International Alliance of Theatrical Stage Employees union, and Willie Bioff, labor racketeer and former pimp. On December 4, 1942 Roselli, a professed U.S. patriot, enlisted in the United States Army. He served as a private until he was arrested March 19, 1943.
In 1943, after a year long trial on the racketeering charges, Roselli and several Chicago mobsters were convicted and sentenced to 10 years in prison. However, in 1947 they were paroled after serving only about three-and-a-half years. It was widely assumed that the Outfit's political fixer, Murray "The Camel" Humphreys, used his influence with President Harry Truman's Attorney General, Tom C. Clark, to spring Roselli and the other Outfit bosses from prison. After his release, Roselli returned to Hollywood in hopes of becoming a movie producer with Bryan Foy.
The extensive influence The Outfit had over Hollywood is best illustrated in 1948 when boss Tony Accardo told Roselli to force powerful Columbia Pictures president Harry Cohn into signing then-unknown actress Marilyn Monroe to a lucrative multi-year contract. The usually combative Cohn quickly complied without opposition, mainly because Cohn had obtained control of Columbia through mob funds and influence provided by both Accardo and Roselli.
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