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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 of the Mob. One robber flunked the test; he was later shotgunned to death, presumably by the Mob.
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.
For reasons still not clear, Cain's influence in the Mob had waned by early in 1973. Some longtime Mafia observers believe that Giancana and Cain had a serious dispute. Others believe that a band of jewel thieves he had fallen in with decided that he could no longer be trusted. Why was he killed? Said one Chicago police investigator: "He knew too much." Added Charles Siragusa, executive director of the Illinois Legislative Investigating Commission: "He may have committed the unpardonable sin—talking to both sides."