Richard Cain was one of the most extraordinary figures in mid-20th century American crime — a decorated Chicago police officer who was simultaneously a made member of the Chicago Outfit, a CIA asset, and an FBI informant. His career defied every category the criminal justice system had for men like him.

Born Richard Scalzitti in 1930 in Chicago, Cain joined the Chicago Police Department and rose quickly through the ranks, earning a reputation as a skilled investigator. Behind that reputation was a man who was using his badge to protect Outfit operations, tip off mob figures to raids, and conduct illegal surveillance on behalf of Sam Giancana, the boss of the Chicago Outfit.

Cain’s relationship with the CIA remains one of the murkier chapters of the Kennedy assassination era. He was involved in the CIA-Mafia plots to assassinate Fidel Castro — a program that also involved Giancana and Johnny Roselli — operating in a grey zone where organised crime and intelligence services overlapped in ways that have never been fully explained.

He was eventually fired from the Chicago Police Department after his Outfit connections became impossible to ignore, convicted of a pharmacy robbery, and served time in prison. On his release he returned to working for Giancana as a fixer and enforcer.

On December 20th 1973, Richard Cain walked into Rose’s Sandwich Shop on the northwest side of Chicago. Two men in ski masks entered behind him, forced everyone to the floor, and shot Cain twice in the head with a shotgun at point-blank range. He was 43 years old. The killing was never officially solved, though it was almost certainly ordered by the Outfit — possibly by Joey Aiuppa, who had replaced Giancana as boss after the latter’s own murder in 1975.

Cain’s life — cop, mobster, CIA asset, informant, murder victim — remains one of the most layered and unresolved stories in the history of American organised crime.