The Hitman's Son: 5 Shocking Truths About Woody Harrelson's Father, Charles Harrelson
The story of Woody Harrelson’s father, Charles Voyde Harrelson, is one of the most bizarre and dark footnotes in Hollywood history, a true-crime saga that continues to haunt the celebrated actor. As of December 21, 2025, the legacy of Charles Harrelson—a convicted hitman and organized crime figure—remains a topic of intense fascination, especially with recent efforts by the Harrelson family to re-examine his case and claims of innocence in his most infamous murder conviction.
The stark contrast between the beloved, laid-back persona of the Emmy-winning actor and the nefarious, violent life of his father, who died serving two life sentences in a Supermax prison, is a compelling narrative of two completely different worlds. This article delves into the verified facts, the conspiracy theories, and the emotional toll the hitman's life had on his famous son.
Complete Biography of Charles Voyde Harrelson: The Convicted Hitman
Charles Voyde Harrelson was a man of multiple identities: a salesman, a gambler, a husband, a father, and ultimately, a professional contract killer. His life was marked by violence, multiple marriages, and long stints in prison, culminating in his death in federal custody.
- Full Name: Charles Voyde Harrelson
- Born: July 23, 1938, in Huntsville, Texas
- Died: March 15, 2007 (Age 68)
- Cause of Death: Apparent heart attack
- Place of Death: ADX Florence Supermax Prison, Florence, Colorado
- Spouses: Married multiple times, including to Diane Lou Oswald (Woody Harrelson's mother)
- Children: Three sons, including actor Woody Harrelson and Brett Harrelson
- Occupation: Encyclopedia salesman, professional gambler, and convicted contract killer (hitman)
- Most Notorious Crime: Assassination of U.S. District Judge John H. Wood Jr. in 1979
- Sentence: Two consecutive life terms plus five years
The Notorious Crimes: Contract Killings and the Federal Judge
Charles Harrelson’s criminal career spanned decades, involving multiple murders-for-hire that cemented his reputation as a ruthless professional hitman. While he was charged three times with murder, two of those cases resulted in convictions, sending him to prison for life.
The Murder of Sam Degelia Jr.
Harrelson's first major conviction came in 1968 for the contract killing of Sam Degelia Jr., a wealthy South Texas businessman. He was initially sentenced to five years in prison but was released early on parole in 1973. This early crime established the pattern of his career: taking money to eliminate targets for organized crime figures.
The Assassination of Federal Judge John H. Wood Jr.
The crime that truly sealed Charles Harrelson's fate—and made national headlines—was the assassination of U.S. District Judge John H. Wood Jr.. Judge Wood, nicknamed "Maximum John" for his harsh sentencing in drug cases, was shot and killed outside his San Antonio home on May 29, 1979.
This event was profoundly shocking, marking the first assassination of a federal judge in the 20th century. Harrelson was hired by drug trafficker Jimmy Chagra, who was facing a tough sentence from Judge Wood. Harrelson was apprehended, tried, and eventually convicted in 1982, receiving two life sentences. He spent the remainder of his life incarcerated, mostly at the infamous ADX Florence Supermax facility in Colorado, the highest-security prison in the United States.
Woody Harrelson’s Lifelong Quest for a Retrial and the New Revelations
Woody Harrelson was only seven years old when his father was first incarcerated and about 20 when Charles was arrested for the judge's murder. Despite the overwhelming evidence and his father’s notorious reputation, the actor has maintained a complex, often painful relationship with Charles Harrelson, going to great lengths to support him.
The Claim of Innocence and the CIA Operative Theory
Woody Harrelson has openly expressed his belief that his father was innocent of Judge Wood’s murder. He spent a significant amount of money and time attempting to secure a retrial for his father, believing the trial was fundamentally flawed. In a stunning revelation, Woody once suggested that his father was not a simple hitman but a CIA operative who may have been set up or operating under orders. This theory is one of the most enduring, if unproven, aspects of the case.
“I’m not saying my father’s a saint but I think he’s innocent of that,” Woody once stated, reflecting his personal conflict and dedication to his father’s defense.
The JFK Assassination Conspiracy
Another layer of shocking complexity is Charles Harrelson’s alleged connection to the assassination of President John F. Kennedy. While under the influence of drugs during his capture for the judge's murder, Charles Harrelson publicly claimed to have been involved in the JFK assassination. Though he later recanted the statement, the claim fueled conspiracy theories for decades, with some speculating he was one of the "three tramps" seen near Dealey Plaza. No credible evidence ever substantiated his involvement, but the mere claim added to his dark legend.
The New Podcast: A Brother’s Reinvestigation
The most recent and compelling development in the Charles Harrelson saga is the launch of a new true-crime podcast, which features Woody's brother, Brett Harrelson, actively reinvestigating their father's murder conviction. The podcast promises new interviews with family members and others who knew Charles Harrelson, aiming to shed new light on the circumstances surrounding Judge Wood's death and Charles’s guilt or innocence. This ongoing effort underscores the deep, generational impact of Charles Harrelson's life of crime on his family, proving that the story is far from over.
The Legacy of a Hitman: Woody Harrelson’s Shadow
Charles Harrelson’s death in 2007 at the Supermax facility brought a final, tragic end to his notorious life, but the emotional and public scrutiny continues for his son. Woody Harrelson has managed to forge a spectacular career in spite of this dark shadow, often citing the experience as a profound influence on his life and his pursuit of social justice and anti-establishment themes in his work.
The story of Woody Harrelson’s father is a stark reminder that even the most famous public figures carry deeply private and often shocking family histories. The enduring mystery of Charles Harrelson—the salesman-turned-hitman who killed a federal judge and claimed involvement in the JFK assassination—is a complex piece of American true crime that will likely be debated for years to come.
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