Charles Harrelson: The Hitman Father of Woody Harrelson

Feb 11, 2023
8 min read

Woody Harrelson is one of Hollywood's most recognisable faces, but the story behind his surname is far darker than anything he's played on screen. His father, Charles Voyde Harrelson, wasn't a troubled man who drifted into petty crime. He was a professional killer, convicted of murdering a sitting federal judge for a quarter of a million dollars. He spent the rest of his life in a supermax prison, claiming, among other things, that he'd also shot President Kennedy. This is that story.

From Huntsville to Houston: A Criminal in the Making

Charles Harrelson was born on 23 July 1938 in Lovelady, Texas, though some sources place his birth in Huntsville, in the same county. He grew up in a family with deep ties to law enforcement, which makes what came next all the more ironic. Several of his relatives worked in the Texas prison system. Charles chose the other side of the bars.

He attended Huntsville High School, where he was reportedly involved in the choir and served as vice president of the poster club. He dropped out before graduating and joined the US Navy, serving as a sonar man. The Navy didn't last long either. He was discharged early, and by the late 1950s he was making his living as an encyclopedia salesman and a gambler. He was apparently good enough at the former to be named Salesman of the Year, but it was gambling that really had his attention.

Mugshot of man, 'POLICE DEPT HOUSTON TEXAS 105118 5-28-60'. — Charles Harrelson, Woody Harrelson’s father, in a mugshot from 1960.

In 1958, he married Diane Lou Oswald in Pasadena, Texas. They had three sons together: Jordan, Woodrow (better known as Woody), and Brett, who also became an actor. The marriage didn't survive Charles's lifestyle. By 1964 they were divorced, and by 1968 he'd disappeared from his children's lives entirely.

In 1960, he was convicted of armed robbery and sentenced to five years in prison, though he served only a fraction of that. It wouldn't be the last time the courts let him walk away earlier than they should have.

Have Gun, Will Travel

At some point in the early 1960s, Charles Harrelson made a decision that would define the rest of his life. He started killing people for money. And in a detail that seems almost too brazen to be true, he reportedly had business cards printed that read "Have gun will travel" and "Hitman." It's the kind of thing you'd dismiss as myth if it weren't so consistently reported.

His first confirmed victim was Alan Berg, a carpet salesman from the Houston area. In 1968, Berg was lured to a bar with a phone call from a woman, then ambushed by Harrelson at gunpoint, forced to drive to a remote location, and killed. Harrelson had reportedly been paid $1,500 by a rival carpet salesman to do it. Berg's brother David later wrote a book about the murder titled Run, Brother, Run, and remains convinced to this day that Harrelson was responsible. The case went to trial in 1968 but ended in an acquittal in 1970.

In a twist that reads like something from a crime novel, the private investigator hired by Berg's father to find his son turned out to be Charles's own brother, Claude, who had no idea his sibling was involved.

Hugo Black, Associate Justice, wearing judicial robe, seated, black and white portrait. — U.S. District Judge John Wood Jr. was known as “Maximum John” for the extremely harsh sentences he gave to drug dealers.

Killing for Pocket Change

Later in 1968, Harrelson took on another contract. Sam Degelia Jr. was a grain dealer from south Texas and a father of four. Someone paid Harrelson $2,500 to shoot him in the head. By the standards of what would come later, it was small money. In total, across the Berg and Degelia killings, Harrelson made $4,000 as a hitman, excluding the Wood job. For a man who would later be hired for a quarter of a million dollars, his early career was remarkably cheap.

The Degelia trial ended in a deadlock on the first attempt. He was retried in 1973, convicted, and sentenced to 15 years. He served five of them before being paroled in 1978 for good behaviour. It was a decision that would cost a federal judge his life.

The Assassination of Maximum John

After his release from prison in 1978, Harrelson spent his time hustling card games, posing as a wealthy doctor or rancher at country clubs to set up marks for other gamblers. He took 25 percent of his employer's winnings. It was a lucrative enough side hustle, but it wouldn't last.

Jamiel "Jimmy" Chagra was an El Paso drug kingpin facing a very serious problem. He was about to stand trial before US District Judge John H. Wood Jr., a man notorious throughout the Texas legal system for handing down the maximum possible sentence to drug offenders. Defendants and lawyers called him "Maximum John." Chagra was facing a potential life sentence and, according to prosecutors, had already tried to bribe Wood for up to $10 million. It hadn't worked.

So Chagra hired Charles Harrelson to kill him instead, for a fee of $250,000. On the morning of 29 May 1979, Judge Wood was walking out of his townhouse in Alamo Heights, San Antonio, heading to work. He stopped to look at a flat tyre on his car. Harrelson shot him once in the back of the head with a high-powered rifle from a distance. Wood died immediately.

It was the first assassination of a sitting federal judge in the United States in the 20th century, and it sparked one of the most expensive investigations in FBI history, eventually costing more than $11 million. For context, that exceeded the cost of the FBI's investigation into the assassination of President Kennedy.

Two solemn men in business suits, one looking down, one facing forward. — Charles Harrelson (far right) in court on October 22, 1981, after his conviction for being a felon in possession of a gun. He would be convicted of murdering Judge John H. Wood Jr. a year later, in December 1982.

The Standoff, the Cocaine, and the Kennedy Confession

Harrelson wasn't caught immediately. It took the FBI over a year, with offices across the country working the case. The breakthrough came from an anonymous tip, combined with a tape recording of a jailhouse conversation between Jimmy Chagra and his brother, attorney Joe Chagra. Over the course of the investigation, federal authorities obtained more than 1,000 recorded conversations, many involving Chagra in various prisons.

When police finally caught up with Harrelson in September 1980, they found him in a cocaine-induced state, firing a gun at imaginary FBI agents. A businesswoman named Virginia Farah, who'd once hired him as a bodyguard and knew him well, was brought in to talk him down. The standoff lasted six hours before he surrendered.

During those six hours, Harrelson made two significant claims: that he'd killed Judge Wood, and that he'd also shot President Kennedy. He later walked back both statements, saying he'd made them in a desperate attempt to "elongate my life" during the standoff. In a television interview after his arrest, he said: "At the same time I said I had killed the judge, I said I had killed Kennedy, which might give you an idea to the state of my mind at the time."

He was convicted of murdering Judge Wood in December 1982 and sentenced to two life terms. His wife Jo Ann received consecutive sentences totalling 25 years for conspiracy and perjury related to the assassination. Jimmy Chagra, represented by Oscar Goodman who would later become mayor of Las Vegas, was acquitted of the murder charges but pleaded guilty to conspiracy. Joe Chagra received a ten-year sentence as part of a plea deal in which he agreed to testify for the prosecution, but refused to testify against his own brother.

Was He One of the Three Tramps?

The JFK claim refused to go away. Conspiracy theorists latched onto Harrelson's physical resemblance to one of three unidentified men detained and photographed by Dallas police in Dealey Plaza shortly after Kennedy's assassination on 22 November 1963. These men, known as the "three tramps," were a subject of speculation for decades. Jim Marrs, in his 1989 book Crossfire, and others suggested Harrelson could have been the tallest of the three.

During Harrelson's trial, his co-conspirator Joe Chagra testified that Harrelson had confessed to shooting Kennedy and had even produced maps showing his whereabouts during the assassination. But Chagra himself was sceptical, and the FBI dismissed any suggestion of Harrelson's involvement. In 1992, the Dallas Police Department finally identified the three tramps as Gus Abrams, Harold Doyle, and John Gedney, effectively closing that particular chapter.

Harrelson never fully let it drop. In 1982, he told a Dallas TV station: "Do you believe that Lee Harvey Oswald killed President Kennedy, alone, without any aid from a rogue agency of the US government or at least a portion of that agency? I believe you are very naive if you do." Whether he was hinting at his own involvement, or just stirring the pot, nobody ever knew for certain.

Man stands with arms crossed inside a small, stark room. — Charles In Supermax

Supermax, Escape Attempts, and Woody's Visits

Harrelson served his sentence in increasingly severe conditions. On 4 July 1995, he and two other inmates at Atlanta Federal Penitentiary tried to escape using a makeshift rope. A warning shot from the prison tower was enough to end it. He was transferred to ADX Florence in Colorado after that, the same supermax facility that housed the Unabomber and, later, various other high-profile criminals.

In a letter to a friend from ADX Florence, he wrote: "There are not enough hours in a day for my needs as a matter of fact... The silence is wonderful." It's an odd thing to read from a man who'd spent his life causing chaos.

Woody Harrelson was seven years old when his father vanished from the family home in Houston in 1968. He didn't reconnect with him until the news of his arrest for Judge Wood's murder broke in 1981. From that point on, he visited his father in prison at least once a year, though he was careful about how he framed the relationship. In a 1988 interview, Woody said: "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."

Woody reportedly spent around $2 million in legal fees attempting to secure his father's release, a figure that speaks to a complicated loyalty that defied easy explanation. Charles had left a prison memoir with instructions for his sons to publish it after his death, maintaining his innocence in the Wood killing while reportedly admitting involvement in dozens of other crimes going back to the early 1960s.

Death in Prison

In 2003, Jimmy Chagra recanted his earlier statements implicating Harrelson in Judge Wood's death, claiming someone else had pulled the trigger. It wasn't enough to reopen the case. Charles Harrelson died of a heart attack at ADX Florence on 15 March 2007, aged 68, having never come close to regaining his freedom.

Whether Harrelson was a brilliant criminal who genuinely outsmarted investigators for years, or a self-promoting small-timer who got lucky until he didn't, depends on who you ask. What's not in dispute is the body count, the two life sentences, and the son who grew up to be famous while his dad rotted in the most secure prison in America.

The Film That Referenced His Father's Crime

There's a footnote to all of this that feels almost too neat to be real. In 2007, the Coen Brothers released No Country for Old Men, their adaptation of Cormac McCarthy's novel set in 1980 Texas, at the height of cartel violence along the border. Woody Harrelson appeared in it as Carson Wells, a smooth-talking bounty hunter hired to track down stolen drug money and eliminate Anton Chigurh. He doesn't make it. Chigurh corners Wells in a hotel room and shoots him dead.

https://www.youtube.com/watch?v=gRcK7Z0q8DM

So Woody is killed on screen by a cartel hitman, in a film set in the exact year his father committed the Judge Wood assassination for a cartel drug lord. But it goes further than that. In McCarthy's original novel, Sheriff Bell's narration actually references the real-life murder of Judge John H. Wood Jr. by a hitman named Charles Harrelson. Woody's father is name-checked in the source material of the very film Woody appeared in.

No Country for Old Men was released later that same year his father died. It's hard to imagine a stranger overlap between Hollywood and real crime.