Charles Harrelson, father of the actor Woody Harrelson, was a card hustler, a self-proclaimed “hit man” and a convicted murderer of a federal judge. A 10-part podcast about the career of the elder Harrelson, Son of a Hitman, is currently available on Spotify. The truth about Charles Harrelson is elusive, ever-changing and perhaps unknowable, even to the podcast’s producer, Jason Cavanagh. David Stewart spoke with Cavanagh for PKM.
On September 1, 1980, near Van Horn, Texas—just 30 miles from the Mexican border—a man was seen shooting the tire of his car in a state of cocaine-induced paranoia. He thought, it was later learned, that someone had planted a surveillance bug in his car. As cops arrived on the scene, the man put the same gun with which he’d shot his tire to his head, claiming that he was responsible for the murder of President John F. Kennedy.
After a six-hour standoff with the police, Texas-based criminal Charles Harrelson was arrested. He wasn’t arrested for his claims of being involved in JFK’s assassination, but for the murder of a federal judge, John Wood. That murder took place on May 29, 1979. One day before passing sentence on marijuana trafficker Jimmy Chagra, “Maximum John” Wood (the nickname based on his merciless sentencing of drug dealers) was gunned down outside his home in San Antonio.
Cut to March 1997: Barbara Walters is interviewing Woody Harrelson in the wake of his Oscar-nominated performance as Hustler publisher Larry Flynt in The People Vs. Larry Flynt. When the conversation steers from Hollywood to Woody’s childhood, Walters asks him about whether his father was innocent for the murder of John Wood. “I’m not saying that my father was a saint, but I think he’s innocent,” Woody responds. When Walters prods further into matters involving his father and his father’s criminal background, Woody nervously responds, “I shouldn’t be getting into this, this is where we could get into trouble.”
Harrelson claimed to have been one of the three boxcar hobos who were not fingerprinted but photographed before President Kennedy’s fateful motorcade in Dealey Plaza.
After a failed escape attempt from the Atlanta Federal Penitentiary, Charles Harrelson was transferred to a federal Supermax prison in Florence, Colorado, where he died in 2007.
Jason Cavanagh, executive producer and host of Spotify’s latest podcast series, Son of a Hitman, was introduced to the Charles Harrelson story by the show’s creator, Andrew Jacobs. From his home in Los Angeles, Cavanagh recalled, “When Andrew introduced the story to me, he said Woody Harrelson’s dad claims that he killed JFK, and I’m going ‘Well, that sounds like bullshit!’ but it’s also that he killed a federal judge, went to prison and served two life sentences for killing a federal judge and this was the only federal judge to be killed up to that point, I’m like ‘Holy Shit! That’s crazy!’”
After acquiring help from private investigators to seek out those who knew of Charles Harrelson and getting the blessing from Brett Harrelson (Woody’s younger brother and executive producer of the podcast), Cavanagh traveled throughout Texas with his Zoom H6 recorder to uncover this mysterious case. As the interviews piled up on his recorder, so did Cavanagh’s theories about Charles Harrelson’s life as a career criminal.
“You have no idea how many times I’ve changed my mind about what the real story is,” said Cavanagh. “Over the course of this, I feel like after every interview, maybe I’m just an easily swayed witness. But after every interview, I’m like ‘Now I know what happened’ and it always goes out the window when I interview the next person.”
Beyond being known as the father of Woody Harrelson, Charles V. Harrelson lived a Jekyll-and Hyde-like existence. He was a well-read lothario and card-shark who picked up women as easily as he could clean out a poker table. But, his bonhomie and gentleman-like grace would change at the drop of a hat. A card-carrying hitman, Harrelson garnered the attention of fellow gamblers and criminals when he became a gun-for-hire leading to the 1968 murders of carpet salesman, Alan Berg, and a grain dealer, Sam Degelia Jr.
For Cavanagh, the characters Harrelson was assigned to kill might as well have been from the movies. “It’s funny, my editor and I saw Uncut Gems, and while we were working on the episode about Alan Berg placing bets (he made a costly bet during the first televised basketball game in 1968 between UCLA and the University of Houston, hailed by sports pundits as ‘The Game of the Century’), he is like Adam Sandler’s character of this gambler placing ill-informed bets, losing the money, and involved with some dangerous people. There’s this overlap of stuff that is very much in the zeitgeist right now.”
It was the murder of Judge Wood that made Cavanagh wonder whether Charles Harrelson pulled the trigger or if someone else carried out the hit and pinned it on the loquacious, card-carrying hitman.
“I’m not going to accuse anybody of anything, but if someone were to want to set somebody up, that’s a perfect patsy, somebody who goes around handing out business cards saying, ‘I’m a hitman who kills people for money’, that’s a great fall guy.”
The business cards Harrelson would give to prospective criminal clients were as shocking as the murders he committed: Wars Fought, Revolutions Started, Assassinations Plotted, Uprisings Quelled, Orgies Organized, (Racial Slur Inserted) Shot For Free. It also begs the question of whether Harrelson was in Dallas on the morning of November 22, 1963.
Harrelson claimed to have been one of the three boxcar hobos who were not fingerprinted but photographed before President Kennedy’s fateful motorcade in Dealey Plaza. Claims can only go so far in what is still considered the biggest unsolved murder in American history. According to Cavanagh, “After being introduced to Charles Harrelson and the myth about him, you start Googling and going down some rabbit holes and you go, ‘okay what’s real and what’s bullshit?’.”
For the information he encountered during the investigation into Charles Harrelson’s life, Cavanagh was determined to not let the case be handled with tabloid-style sensationalism. “One of the things I set out to do was to take all this information that’s out there, put it in one place and try to get a holistic picture of what this guy really was. Is it realistic for Harrelson to kill the President of the United States and then go do these Texas backwoods crimes? It reminds me of Blood Simple: this noir, Texas backwoods thing, and this guy just killed JFK five years ago? And then, he kills a federal judge in 1979, which goes to this other level. But it’s just like ‘Who the fuck is this guy?’”
Another Coen Brothers movie that springs to mind listening to the podcast was No Country For Old Men as Woody Harrelson’s Carson Wells tells Josh Brolin’s Llewelyn Moss: “He’s a peculiar man. You could even say that he has principles. Principles that transcend money or drugs or anything like that. He’s not like you. He’s not even like me.” 
Regarding Woody, he’s the only one out of Charles Harrelson’s three sons who hasn’t given an interview for the podcast. As Cavanagh points out, “I wanted to compare notes with Woody to see what he knew and where there’s consistency in the things I’ve found and whether he knows anything beyond what I found. Obviously, I can’t speak for Woody, but I think there’s something deeper there. For me, it wasn’t important that we got Woody the celebrity because that’s not what the story is about. It’s interesting that Woody is this A-list actor and his dad is this character, but it’s not essential to the story. More so, it’s just what does Woody know that other people might not know?”
Son of a Hitman – trailer
https://youtu.be/0IkVyci9kEw
As Cavanagh is wrapping up the final episode of Son of a Hitman, he reflects on how Please Kill Me was a touchstone into his foray as an investigative journalist. “I loved PKM because you get the stories firsthand from the people who lived the punk life and I think that, at its best, that’s what we do in this podcast; we talked to the people who were there, who were around this stuff and even though they are no longer living that life, they were present for it and they can tell at first-hand what it was like and what happened. In a way, it’s bringing that history and past to the present. I think that there’s so much out there in movies and TV about hitmen and this is the real story, the real shit, not something dreamed up by a screenwriter and you get it firsthand with this show.”
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All ten episodes of Son of a Hitman are available on Spotify.
