The rubout was executed neat Chicago gangland style. Two armed men —wearing ski masks and carrying a walkie-talkie to get word from a lookout —slithered into Rose's Sandwich Shop on the hairy, scary West Side. "Up against the wall!" they ordered the eight people inside. One of the gunmen then shoved a twelve-gauge shotgun under the chin of Richard Cain, 49. The hit man fired two blasts, blowing away Cain's handsome face. The killers quickly fled, accompanied by what witnesses later said was a mysterious "woman in blue."
Thus ended Cain's remarkable double-dealing life as a policeman and mobster. Cain was a Chicago detective in the 1950s, and later became chief investigator in the Cook County sheriffs office. In the mid-1960s he was dismissed from the sheriffs office for concocting a phony drug raid, and he became the chief operative of Chicago Mafia Overlord Momo Salvatore (Sam) Giancana. In 1966 Giancana left Chicago for Mexico to avoid federal heat and counseled the Chicago syndicate from his exile; Cain was a trusted aide.
For Cain, the line between the law and the lawless had always been fuzzy. Born in a tough neighborhood not far from where he died, the street-wise Cain left school after eighth grade, but did a good job of self-education. He learned five languages, mastered many of the techniques of eavesdropping and once studied law books for several months. When he later faced conspiracy and other charges, he creditably defended himself in court. Handsome and spectacled, Cain was polite, well read and intelligent. At the same time, he had a hedonist's love of flashy clothes and big cars, and surrounded himself with a stable of women—some of them prostitutes who gave him valuable information about vice rings.
In a taped conversation with officials of the U.S. Department of Justice in 1969, Cain admitted that his Mafia and police careers were inextricably linked. Through the influence of a Democratic politician in Chicago's inner city First Ward, he got a job as a detective in 1956. He soon became the Mob's bag man in the police department, paying off detectives to insure freedom of operation. He was finally compelled to quit the force in 1960, when he and another detective were discovered wiretapping the offices of Mayor Richard Daley's Commissioner of Investigations to secure possibly damaging information that might be used against the Mayor in a political campaign.
For two years afterward Cain was a private detective, and he developed his skills in electronic eavesdropping. He claimed that he worked with the CIA in Central America, training Cubans for the Bay of Pigs invasion. By 1962 he was back in Chicago, where he worked for the election of Richard Ogilvie as Cook County sheriff. Cain said that he told Ogilvie: "I know the hoods. I am not afraid of the hoods, and I hate the hoods." Despite warnings about Cain's Mob connections, Ogilvie hired him, later made him chief of investigators.
Throughout his tenure in the sheriffs office, Cain was collecting $1,000 a month from Giancana to divert Ogilvie's attention from mob activities and to feed inside police information to the syndicate. But he also told the police about out-of-favor mob figures whom he wanted to have arrested in order to solidify his position within the syndicate.