Word: caine
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...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...
...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...
Phony Raid. Cain's successful double-dealing broke down in 1964 after he planted $43,000 worth of drugs in a motel, then staged a "raid" and claimed to have "recovered" the drugs. When Ogilvie learned that Cain had plotted the phony raid to make himself look good, he fired him. During the FBI investigation brought on by Cain's dismissal, it was discovered that, while on the sheriffs staff, he had helped the Mafia smoke out a suspected stoolie in its midst by having a lie detector test administered privately to five bank robbers-for the benefit...
...Cain was jailed in 1969 on charges of conspiracy, concealment of evidence and acting as an accessory to a robbery. Paroled in 1971, he resumed his role as Giancana's right-hand man, serving both as international courier and scout for gambling operations and investments in corporations in Europe and elsewhere...