The Underworld Podcast
Episode: The Weed Kingpin who Hired Woody Harrelson’s Hitman Dad
Date: January 13, 2026
Hosts: Danny Gold & Sean Williams
Overview
This episode explores the dramatic saga of the Chagra family: three Lebanese-American brothers who rose from the borderlands of El Paso, Texas and Ciudad Juarez to become pivotal figures in 1970s U.S. drug smuggling—and, in a stunning escalation, orchestrated the only successful assassination of a federal judge in modern American history. The tale entwines the psychedelic gold rush of cross-border weed trafficking, Las Vegas high-roller excess, court corruption, and murder for hire—culminating with the involvement of notorious hitman Charles Harrelson, the father of actor Woody Harrelson.
Key Discussion Points & Insights
1. Setting the Stage: El Paso’s Underworld
[00:53–05:53]
- The Chagras’ World: The episode opens in late-1970s El Paso, where drug smuggling thrives amid the newly formed DEA’s struggles to contain it. The border town becomes a crucible for criminal defense attorneys and aspiring kingpins alike.
- Lee Chagra: The eldest brother is a flamboyant, wildly successful criminal defense lawyer with a penchant for high-stakes gambling, earning both fame and suspicion from the Feds.
- Backdrop of Violence: The family’s orbit is defined by both criminal opportunity and hovering danger: attempted hits, relentless investigations, and ultimately, Lee’s shocking murder.
"It's a story about three brothers, Lee, Jimmy and Joe, who rose from humble beginnings to become central figures in one of the most audacious criminal conspiracies in United States history."
— Danny Gold [04:30]
2. Chagra Family Deep-Dive: Roots, Rackets, and Gambles
[14:23–23:00]
- Lebanese Immigrant Story: The Chagra patriarch, Joseph, flees Lebanon for Mexico, then lands in El Paso during the Mexican Revolution, reflecting broader patterns of Levantine immigration in Latin America.
- Lee’s Rise: From hustling in a high-school gang (“the Gents”) to scraping through college and finishing near the top of his law class, Lee’s arc pairs hard work with a growing appetite for risk.
- Style and Repute: Lee quickly earns Robin Hood status as a lawyer "with a gold bracelet that says Freedom on it in big letters" [21:30]—beloved by clients, notorious with the authorities.
"Lee had an affinity for cards and dice, for dope dealers and shady politicians and nightclub singers, for dabblers in the black market and exponents of the fast buck. They were all scammers, everyone he knew or cared about."
— Gary Cartwright (quoted by Danny Gold) [24:17]
3. Marijuana Smuggling Empire: Jimmy’s Ambition and Innovation
[35:44–42:44]
- Jimmy Chagra: The “screw-up” middle brother finds his stride in drug smuggling, leveraging family connections and a fearless entrepreneurial streak.
- Scaling Up: Inspired by Vietnam-vet pilots and bold plans, Jimmy transitions from small-potatoes Mexican weed runs to multi-ton Colombian deals, shipping “tramp steamers” full of high-grade pot through Massachusetts Bay and, later, South Florida.
- Distribution Power: At their peak, the Chagra/Strickland crews are running “a fleet of six planes and four freighter ships” with bribed officials, laundering millions through Vegas.
- Mob Connections: Ties to the Boston mafia surface; proceeds feed Jimmy’s and Lee’s gambling frenzy.
“He’s going to bring in 50,000 or so pounds of it from Colombia on a tramp steamer, which is also known as a big ass ship.”
— Danny Gold [38:12]
4. The Legal Pressures Mount & Personal Stakes Get Deadly
[42:44–51:14]
- Federal Pursuit: Prosecutors and Maximum John Wood, a judge infamous for his harsh drug sentencing, zero in on the Chagras, especially Lee, whom the Feds suspect as the real kingpin.
- Near Misses: Jimmy’s empire is repeatedly dented by failed runs and busted associates, but the brothers continually slip prosecutorial nets due to lack of evidence.
- Violence Escalates: A failed assassination attempt on prosecutor James Kerr (shot at 19 times, survives) is later linked to Jimmy Chagra. The situation spirals out of control.
5. Lee Chagra’s Murder: Mystery and Revelation
[51:21–54:34]
- Lee’s Death: In December 1978, Lee is gunned down in his law office; $450,000 in cash disappears—money reportedly owed to mafia boss Joe Bonanno.
- Investigation: Wild speculation ensues—family, organized crime, or federal agents as culprits? Eventually, two soldiers confess: spurred by a distant, drugged-out relative of Lee’s, their clumsy robbery turned fatal.
- Financial Trail: The missing cash links the Chagras directly to the upper echelons of the mafia, while Lee’s death leaves Jimmy feeling vulnerable.
6. The Assassination of Judge John Wood
[55:18–71:54]
- The Contract: Fearing that without Lee’s protection he’s doomed to spend life behind bars under Judge “Maximum John” Wood, Jimmy seeks a way out—and finds it in Charles Harrelson, a gambler and hitman.
- Woody Harrelson’s Father: Charles Harrelson is notorious for murder-for-hire and becomes a heavy presence in the Vegas underworld.
- The Hit: Judge Wood is shot dead with a sniper’s bullet in May 1979 outside his San Antonio condo—the first federal judge killed in over 100 years.
- The Manhunt: An epic federal investigation ensues, slowly focusing in on the Chagras and Harrelson.
"A federal judge, the first one killed in over a century. And this is a big deal. The killer disappears, blends into traffic. A real pro."
— Danny Gold [58:24]
7. Trials, Pleas, and Twisted Endings
[68:28–73:49]
- Legal Circus: As details emerge, a convoluted web of confessions—some true, some coerced or fabricated—entangles Joe Chagra, Jimmy’s wife, and Harrelson himself.
- Celebrity & Scandal: The trials are a media event. At one point, Harrelson even claims to have killed JFK (eventually ruled baseless).
- Judgments: Harrelson receives two life sentences; Jimmy’s wife gets 30 years; Joe flips and gets 10 (serves 6.5). Thanks to his ace lawyer, Oscar Goodman, Jimmy is found not guilty in the murder trial, but remains imprisoned for drug charges.
- Closure: Years later, Jimmy confesses to orchestrating the judge’s murder and the hit on prosecutor Kerr in exchange for his wife’s release (unsuccessful; she dies in prison). Jimmy is paroled in 2003, dies in obscurity. Charles Harrelson dies in prison; his son Woody campaigns for his release, to no effect.
"Jimmy hires his brother Joe. He hires Goodman. And he's also convinced at this point that Judge Wood and the D. A and everyone are corrupt, that they're out to get him, that they had Lee killed."
— Danny Gold [55:18]
Notable Quotes & Memorable Moments
On the Mythmaking of Kingpins:
"If you smoked weed in the US in the 70s, it probably came from him, which all of that seems like an extremely implausible... just having done all the stories we’ve done on smugglers in that era... I don’t think there’s any way that’s true, but you’ve got to, you’ve got to move stories, got to get those superlatives in the headlines."
— Danny Gold [10:33]
On Vegas Excess:
"The dude loves to run at the tables to the point that by the late 60s, Vegas casinos are sending Learjets to pick him up... swinging 60s, Rat Pack, Sinatra, old school mafiosos, glamour and glitz. And Lee is all about it."
— Danny Gold [24:17]
On the Judge’s Ruthlessness:
"Wood believes deeply, like almost religiously, that the drug trade is destroying America... When drug defendants appear before him for sentencing, Wood shows absolutely no mercy. None."
— Danny Gold [48:18]
On the Ultimate Irony of the Chagras’ Fall:
"Harrelson receives two life sentences; Jimmy’s wife gets 30 years for delivering the payoff, which seems pretty harsh. Haron gets two life sentences. But, you know, it is the murder of a federal judge."
— Danny Gold [69:26]
Key Timestamps & Segments
- [00:53] Intro to the Chagras and El Paso's criminal boom
- [14:23] Chagra family origins and Lee’s early years
- [21:30] Lee invents himself as high-profile defense lawyer and gambler
- [35:44] Jimmy enters the weed game, scales up to international shipments
- [42:44] Pressure from law enforcement, near-miss assassinations, legal jeopardy
- [51:21] Lee’s murder and the ensuing chaos
- [55:18] Hiring Woody Harrelson’s hitman father, the assassination of Judge Wood
- [61:08] Jimmy on the run, capture, and judicial aftermath
- [68:28] Bizarre and sensational murder/conspiracy trials
- [71:54] Final disclosures, fate of the Chagras, Harrelson, and lasting legacy
Tone & Style
The hosts combine wry, irreverent humor with a gritty, detail-heavy narrative, mixing underworld romance (“He sounds like a good time!” [24:19]) with journalistic skepticism of the myth-making around drug kingpins. The banter knits the story’s sprawling criminal web together, keeping the energy up even as events spiral into tragedy and absurdity.
Conclusion
The Chagra family’s rise and fall is a jaw-dropping tale that blurs the lines between defense attorney and kingpin, between Las Vegas high life and federal court doom. Their world connects Mexican border smuggling, American mafia intrigue, and the wildest corners of legal excess. The murder of Judge Maximum John Wood remains a singular, shocking moment in U.S. criminal history—and the involvement of Woody Harrelson’s hitman dad only adds to the legend. In true Underworld Podcast fashion, the episode is a panoramic tour of greed, violence, and the lure (and cost) of risk on the American periphery.
Listen to the full episode for even more intricate details, mad escapades, and the unmistakable signature banter of Danny and Sean.