Caifano immigrated to Chicago from Italy in the 1920s and became affiliated with the Chicago Outfit and mobster Paul Ricca. Caifano was a boxer in his youth. In the 1940s, Caifano was sent to Los Angeles. According to author Gus Russo, Bugsy Siegel, who was building a gambling establishment in Las Vegas, was at Beverly Hillshome with Caifano associate Alan Smiley when another man arrived; Siegel was shot to death, and soon after Gus Greenbaum, the Chicago Outfit's chief bookie, arrived at Siegel's Flamingo Hotel in Las Vegas and said, "We're taking over." In 1943, Nick Circella, Caifano's associate, was tried for extortion trial of his girlfriend, Estelle Cary who was about testify against him until her burned and stabbed body was later found. Caifano was suspected of the murder, but the case was never solved; he was also suspected of several other unsolved killings, including the 1950 murder of former Chicago Police Lt. William Drury, the 1952 strangulation of mobster "Russian Louie" Strauss and the 1973shotgun killing of Police OfficerRichard Cain. In the 1950s, the Outfit moved in on the business of black mobster Theodore Roe, a tried to kidnap him, but Roe killed Caifano's brother during the botched kidnapping attempt in 1951. Roe was tried and pleaded self-defense, but a year later, Roe was shot to death; Caifano and Giancana were questioned but never charged.
Prison and death
In 1964, Caifano was convicted of extorting $60,000 from oilman Ray Ryan, who testified against him. The conviction was upheld in 1966, and Caifano was sentenced to 10 years in prison. Caifano was sentenced to a further 12 years in prison, in 1967, for defrauding a lumber dealer of $42,000. When Caifano was released from prison in the 1970s, Ryan reportedly offered him $1 million in restitution, however, in 1977, Ryan was killed in a car bomb; no one was charged in the murder. In 1980 Caifano was sentenced to 20 years for fencing stolen stock certificates. A few years after Caifano was released from prison, he died of natural causesin September 2003.
