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.