It is likely that Humphreys had a hand in arranging the 1933 fake kidnapping of John "Jake the Barber" Factor, a British con artist wanted in England for stock swindling. Factor, a Capone friend, was facing extradition proceedings when the Outfit staged a fake disappearance and framed Capone rival Roger "Terrible" Touhy for allegedly kidnapping Factor. Touhy received a 99-year prison sentence but was released in 1959, only to be murdered several weeks later. Six months after Touhy's death, Humphreys supposedly bought several shares of an insurance company and eight months later redeemed the shares for $42,000. An Internal Revenue Service (IRS) investigation soon determined that these shares had been originally owned by John Factor. The IRS claimed that the $42,000 was a payment from Factor to Humphreys for the fake 1933 kidnapping; they forced Humphreys to declare the money as income and pay taxes. Other career highlights for Humphreys include his discovering and exploiting the intricacies of the legal system's "double jeopardy" rule and the U.S. Constitution's Fifth Amendment for the Mob's benefit. When Jake "Greasy Thumb" Guzik died in 1956, Humphreys became the Outfit's chief political fixer and financial manager or, in the words of one Mafia historian, their "strategist, councilor, and master schemer". Knowing that Guzik's body could not be found at the restaurant without compromising some of the Outfit's most valuable judicial resources, Humphreys had the body surreptitiously removed from the restaurant and taken home to Mrs. Guzik, who was curtly informed that her husband had officially died at home. Giancana and his much valued "adviser" had rather dissimilar styles, illustrated by the following: both men were constantly tailed by Federal agents, but when Giancana grew impatient of a car tailing him, he put his foot to the gas and brought about a race between him and his pursuers. Humphreys, however, one day when he had had enough of being followed, got out of his car, sent his driver home, went up to the car that was following him and said: "You've been following me all day. There's no need for two cars. I'll ride with you." (He did just that, and apparently even bought the officers lunch.) Sam Giancana and Murray Humphreys both topped the FBI's Top Hoodlum list, "Top Hoodlum" being a program put into operation in 1957 for the purpose of combating organized crime and the Mafia in particular.