Woody Harrelson’s Dad Was a Professional Hitman?

Woody Harrelson’s carved out an impressive career for himself as a versatile actor in movies and TV shows. He overcame a lot of trauma to get there. His childhood was a harsh one partly because of the desertion of his father, Charles Harrelson.

He eventually made himself known in a particularly disturbing way: as a hitman and convicted murderer with tangential connections to one of the most enduring conspiracy theories of the 20th century. 

Harrelson grew up in a difficult environment without his father

Harrelson was born in Midland, Texas, and primarily raised by his mother, Diane, alongside his two brothers, Brett and Jordan. The considerable amount of money he’s made as an adult is a stark contrast to the conditions he was raised in. “We were poor,” he said to the Financial Times.

“But my mom always took care of us [and] we always had food. It was a lot to raise three kids on her own as a secretary but she did it and she sure did look after us.”

It was a Presbyterian household, and his religious background nearly set Harrelson on a different career path. He told Esquire in 2019 that he considered joining the ministry before committing to acting. 

But those teachings did little to quell the storm that roiled inside him. Harrelson describes himself in the same article as having “a lot of anger, a lot of rage” as a kid. He got himself kicked out of nursery school and did the same in the first grade after punching through windows in response to being accused of stealing a teacher’s purse.

He then attended Briarwood, a private school in Houston, where his behavior improved. The family then moved to Lebanon, Ohio, when he was 12. Charles Harrelson was not present in Woody’s life. He and Diane separated when Woody was seven, and he spent the majority of his kids’ childhood in prison. 

Charles Harrelson became a famous name for the wrong reasons

While Woody was trying to find his way in the world with the rest of his family, Charles worked as a professional gambler and hitman, according to All That’s Interesting. His first run-in with the law was when he was convicted of armed robbery in 1960. Harrelson was first tried for murder in 1968 for the death of a carpet salesman named Alan Berg, but he was acquitted by a jury. 

In 1973, he was convicted of killing a Texas grain dealer named Sam Degelia Jr., which led to a 15-year sentence in prison. He was released after five for good behavior. Not long after getting out, he was implicated in the death of U.S. District Judge John Wood Jr. This was a historic crime. Wood Jr. was the first federal judge to be assassinated in the 20th century.

After a standoff with the cops, Harrelson was apprehended and eventually sentenced to two life sentences behind bars. Evidence confirmed that he received $250,000 from drug kingpin Jamiel “Jimmy” Chagra, who was concerned about Wood’s strong stance on drug offenses.

Harrelson’s wife at the time, Jo Ann, was also sentenced to 25 years on multiple counts of conspiracy and perjury, though she was later paroled. During that stand-off with the cops, Harrelson also claimed to be the killer of John F. Kennedy, but his involvement, in that case, has been mostly disregarded. 

Woody learned about the state of his dad’s life inadvertently. He revealed to The Guardian that he heard about his dad’s trial over the radio when he was 11.

“I was in the car waiting for a lady who was picking me up from school, helping my mum, and anyway, I was listening to the radio, and it was talking about Charles V. Harrelson and his trial for murder and blah blah blah blah and I’m sitting there thinking there can’t be another Charles V Harrelson … I mean, that’s my dad! It was a wild realization. Then the woman got in the car and saw my face and realized something was up. She was a very kind lady.”

Despite questions about his case, Harrelson spent the rest of his life behind bars

Prior to his death, Chagra recanted his claims that Harrelson committed the crime, saying that someone else shot Wood. Woody, now an established performer, funded his father’s appeals as he thought his father was a “victim of prejudicial pretrial publicity.” Woody also noted the judge who convicted his father was one of the pallbearers for the murdered judge, according to Snopes.

Charles was found dead in his cell in 2007 after suffering a heart attack. He was 68. 

In a piece for The Hollywood Reporter, Woody eulogized his dad with an impressive amount of acceptance and forgiveness, referring to him as a man with “an incredible intellect, but he went down the wrong path.”

“My dad’s main thing to me and my brother, growing up, was: Keep an open mind. That’s what he said: ‘All I’m asking is, keep an open mind’ … That’s pretty good advice from a father.”

For a more in-depth look into Charles’ life, you can listen to Son of a Hitman, a 10-episode Spotify podcast that re-examines his life and features interviews with Brett and Jordan Harrelson. Woody did not participate in the podcast. 

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