Woody Harrelson’s Dad: Everything To Know About His Infamous Hitman Father, Charles

Woody Harrelson is a beloved Hollywood actor, but he comes from a troublesome legacy. Find out more about his hitman father, Charles Harrelson, here.

Woody Harrelson is known for some major films in Hollywood, like his star-making turn in White Men Can’t Jump and subsequent hits like Zombieland and Natural Born Killers. What fans of the famous actor may not know is his father has an extremely checkered past, with participation in drug rings and charges for murder.

Here we break down everything to know about Woody’s father, Charles Harrelson, who was heavily involved in organized crime.

Charles Harrison: Hitman-For-Hire 

Born July 23, 1938 in Lovelady, Texas, Charles Harrison first worked as an encyclopedia salesman in California before turning toward living life in the fast lane, first as a professional gambler. Then, in 1960, he was convicted of armed robbery, and soon turned more to the dark side as a hitman-for-hire. Charles first murdered Alan Harry Berg. He was tried on May 28, 1968 but was ultimately acquitted on Sept. 22, 1970 by a jury in Arlington, Texas.

Following his acquittal, he was then hired for $2,000 (the equivalent of $15,000 in 2020) to kill Sam Degelia, who was a grain dealer and father-of-four in McAllen, Texas. Although the trail ended with a deadlocked jury, Charles was retried in 1973 and sentenced to 15 years in prison. In 1978, after serving five years, he was released on good behavior.

Charles’ Biggest Crime 

Although Charles was released from prison for his “good behavior,” that didn’t last long, as he was then hired by Texas drug lord Jimmy Chagra for $250,000 to kill U.S. District Judge John H. Wood Jr., aka “Maximum John” who was named as such due to his long sentences for drug offenses. Before Chagra was set to be tried, Charles shot the judge in the small of his back with a single bullet on May 29, 1979 as he was getting into his car. It was the first U.S. federal judge to be murdered.

Following the murder, an intense manhunt ensued, and Charles was finally found by the FBI via an anonymous tip and tape recording of a conversation between Chagra and his brother Joe Chagra when the latter visited the former in prison. While Charles claimed at the trouble he didn’t kill the judge, he did somewhat take credit in order to received the payout from Chagra. He was ultimately sentenced to two life terms and both Charles and Joe Chagra were implicated in the assassination and Chagra received a ten-year sentence. Charles’ wife at the time, Jo Ann Harrelson, was also implicated in the murder and was sentenced to consecutive terms totaling 25 years on convictions of conspiracy and perjury related to the assassination.

Charles passed away on March 15, 2007 at age 69 while still serving time in Colorado’s Supermax federal prison.

He & Woody’s Relationship 

Woody — born Woodrow Harrison in Midland, Texas — apparently wasn’t aware of his father’s troubled past until he was listening to the radio one day. The actor heard the announcer discuss the murder trail of Charles V. Harrison and asked his mom if there was any relation. After his mother confirmed it was indeed his father, Woody actually tried to reconnect with his dad in the ’80s, and even went on to spend $2 million to try and get his father a new trial.

Although he wasn’t successful, he still tried to have a reasonable relationship with his dad and see his humanity, once telling The Sunday Times in 2007 that he sees the “mixed influence” his father may have had on him. “It made me think outlaw, but I would not want to hurt anyone,” he told the outlet.

Woody also told PEOPLE in 1988, “My father is one of the most articulate, well-read, charming people I’ve ever known. Still, I’m just now gauging whether he merits my loyalty or friendship. I look at him as someone who could be a friend more than someone who was a father”