The hitman who claimed to kill a president and a judge

Cultures · Published 11 October 2026 Swipe more like this →

In short: Charles Harrelson was more than a contract killer; he was a figure of enduring mystery. Convicted of assassinating the first federal judge killed in the 20th century, his life oscillated between professional crime, high-profile litigation, and bizarre claims that linked him to one of America's most famous unsolved mysteries.

Charles Harrelson was a prolific criminal figure whose career included roles as an encyclopedia salesman, professional gambler, and contract killer. In 1970, he was acquitted in the murder of Alan Harry Berg, but his later crimes were more definitive. He was convicted for the 1968 murder-for-hire of grain dealer Sam Degelia Jr., for which he received a 15-year sentence. After being released in 1978, Harrelson became implicated in the May 29, 1979, assassination of U.S. District Judge John H. Wood Jr. in San Antonio.

The prosecution's case against Harrelson for the judge's murder relied heavily on a tape recording of a conversation between drug dealer Jamiel Chagra and his brother, attorney Joe Chagra. While Harrelson claimed he only took credit for the killing to secure payment from Chagra, he was sentenced to two life terms. The case remains complex: in 2003, Chagra recanted his statements, claiming someone else pulled the trigger, while Harrelson's son, actor Woody Harrelson, unsuccessfully attempted to overturn the conviction.

Harrelson’s legacy is further clouded by his claims regarding the assassination of John F. Kennedy. During a 1980 police standoff, he confessed to killing both Wood and Kennedy, though he later described these statements as an effort to 'elongate' his life. Despite FBI skepticism, some theorists point to forensic artist matches and historical accounts suggesting Harrelson may have been one of the 'three tramps' arrested in Dallas shortly after the shooting.

Harrelson spent his final years in the supermax prison ADX Florence, where he reportedly enjoyed the silence. He died of a heart attack in 2007 at age 68. His life has since inspired popular culture, including Cormac McCarthy's 'No Country for Old Men,' which references the Judge Wood murder, and a podcast investigating the legitimacy of his various criminal charges.

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