Before returning to Chicago in 1951, Cain worked as an investigator at the Burns Detective Agency in Dallas, Texas.

[1] Despite his grandfather having been a prominent sewer contractor who was killed by the Chicago Outfit in Little Italy, in 1928,[2] Cain would later become a close associate of Sam Giancana.

Cain alluded to having been deported from Mexico in 1961 after helping train Cuban-Americans for the Bay of Pigs invasion.

[3] He also claimed to have worked with the U.S. State Department "tracing the flow of American money into Communist hands.

"[1] Cain returned to Chicago in early 1962 to support Ogilvie in his campaign for Cook County Sheriff.

After parole, Cain made "frequent trips" to and from Mexico as Sam Giancana's courier and financial adviser.

[1] Cain became a key figure in Giancana's money skimming from casinos in Central America and Iran.

[11] According to Michael J. Cain, there was no evidence to support the rumors that his half-brother was directly involved in the assassination of John F. Kennedy as a gunman.

[12] Richard Cain was at the Criminal Courts Building 26th & California, Chicago, Illinois the day of the Kennedy assassination - per John J.