By the mid-1960s, Charles Harrelson had moved to Houston and was earning his living primarily through gambling — a transition that placed him in proximity to the specific world of organized crime, loan sharking, and debt that Texas gambling of that era occupied. Professional gambling, even when the gambling itself was legal, existed in a social ecosystem that was not governed by the formal rules of business. Disputes were resolved differently. Enforcement was different. And the people who moved in that world included people for whom violence was an available tool.
Harrelson became, in that world, someone who offered a specific service: he killed people for money. The in-prison memoir material he eventually produced claimed involvement in dozens of such contracts before he left his family in 1968. These claims are not independently verified and are attributed to a man who had demonstrated, by the time he made them, a complicated relationship with the truth. What is verified is the beginning of a documented criminal career as a murderer for hire.
He had married Diane Lou Oswald in 1959. The marriage produced three sons: Jordan, the oldest; Woodrow, born in 1961; and Brett, the youngest, who also eventually became an actor. The family lived in Midland, Texas — an oil-economy city in West Texas that would be, for the sons, the geography of their earliest years, before the family subsequently relocated to Houston. By 1968, Charles was gone. He left his wife and his three sons and went further into the criminal world that had been his actual occupation for years.