Milano was born in 1925 in Cleveland, Ohio to Anthony and Josephine Milano. His father was underboss of the Cleveland crime family from the 1930s until his retirement in 1976. Many members of the Milano family were involved in organized crime, including his uncle Frank Milano, who was boss of the Cleveland family and sat on the original Commission from 1931 until he chose to flee the country to avoid tax evasion charges in 1935. His brothers were also involved in the Mafiaexcept forCarmen Milano who chose to be a lawyer until eventually also becoming a mobster in the 1980s. He is also related through marriage to John Nardi who was a Mafia associate who was killed for switching sides to the Irish Mob, during the Cleveland family's war with Danny Greene. Milano moved with his family to Beverly Hills, California in the late 1930s or early 1940s as a teenager. After graduating from high school, Milano became a part of Mickey Cohen's syndicate and was involved in illegal gambling.
Mafioso
After switching allegiance to the Los Angelescrime family, Milano became a made man in 1970. Soon after, he was promoted to caporegime in the family. His father Anthony, while also being one of the main criminal powers in Cleveland, also had interests on the West Coast and was closely associated with the L.A family. In March 1973, Milano and six others were charged with running a rigged gambling operation in Los Angeles that brought in up to $250,000 a month. Their trial was delayed when the key informant and witness, former Mafia associate John Dubcek, was shot and killed in Las Vegas. Although this scared other informants from testifying, Milano was still sentenced to four years in prison. Months later Milano and 11 other men were indicted for conspiracy, racketeering and extortion against bookmakers, loan sharks, and pornographers. Milano served four years for both indictments.
Boss
In 1981 the top members of the Los Angeles crime family, including boss Dominic Brooklier, were sentenced to jail time on RICO charges. This left a power vacuum in the family and enabled Milano to step up and become acting boss. With Brooklier's death in 1984, Milano was made boss of the family and named his brother Carmen his underboss. Milano took charge of a depleted family and was successful in having illegal bookmakers pay tribute to his family, which was already heavily involved in extortion. In 1984 he was arrested for trying to take over a $1 million a week book making operation, but was released due to lack of evidence. In March 1988, Milano pleaded guilty again to racketeering charges and received a six-year prison sentence. He never acknowledged being a part of the Mafia. On April 4, 1991, Milano was paroled from prison. He was able to avoid any jail time from the Las Vegas indictments brought on by the murder of Herbert Blitzstein in 1997.
