Killer Stories with Harvey Guillén - Judge Killer: Charles Harrelson

Episode Date: May 15, 2023

While many know his son, Oscar-nominated actor Woody Harrelson, Charles Harrelson spent most of his adult life on the wrong side of the law. As a contract killer, he successfully killed his first two targets but went to trial for both. Years later, he was back on the streets, ready to make a big payday. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Due to the nature of this episode, listener discretion is advised. This episode includes discussions of murder, gun violence, psychosis, drug use, and gambling. Consider this when deciding how and when you'll listen. To get help on mental health, visit Spotify.com slash resources. When you think of a hitman, you probably picture a professional, somebody who approaches killing in a cautious, dispassionate way, operating by strict rules which they've honed over many hits. After all, you don't make a living from murder by being sloppy.

Unlike other types of financially motivated crimes like burglary or fraud, contract killing isn't typically the kind of thing you just stumble into, and it isn't usually something you do for kicks. Unless that is, you're Charles Harrelson. A lifelong thrill-seeker and Lothario, with a penchant for gambling and cocaine, Harrelson was no professional. In fact, he often bragged that he'd never done an honest day's work in his life.

As a hitman, he made at most $4,000, and he never even got paid for the hit that ended his brief, chaotic career. So how does a small-time criminal become the stuff of legend? Hi, listeners, it's Greg. You're listening to Serial Killers, a Spotify original from Parkast. I'm here with my co-host, Vanessa. Hey, everyone. Today, we're continuing our series on Hit Men.

These episodes explore the twisted world of contract homicide, both the people who kill and those who hire them. Nowadays, Charles Harrelson comes up most often as a curious footnote in the life of his much more famous son, the actor Woody Harrelson. Charles's notoriety is a little different, though. During the 1970s, he became infamous in Texas, after murdering a federal judge in broad daylight. We've got all that and more coming up. Stay with us.

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Try Activia today. Enjoying Activia twice a day for two weeks as part of a balanced diet and healthy lifestyle may help reduce the frequency of minor digestive discomfort. which includes gas, floating, rumbling, and abdominal discomfort. It was a hot afternoon in September 1980, in a sandy sun-blasted corner of Texas, not far from the Mexican border, something strange was unfolding. A dishevelled man in his 40s stood at the side of the I-10 highway,

yelling and wildly gesturing into the air. Motorists slowed down to rubberneck, then sharply accelerated away when they realized something. The man had a gun. He wasn't focused on passers-by, though. Instead, he pointed the 44 Magnum at his parked car and fired several shots into the rear bumper. He then aimed the gun at his head. Several people called the cops, reporting that a drifter was holding himself hostage on the side of the highway.

None of them had any idea that they were actually turning in a wanted man. When the police arrived, they recognized him immediately as 42-year-old Charles Harrelson, A fugitive with a long rap sheet who was the lead suspect in the high-profile murder of a prominent San Antonio judge. He'd been on the run for weeks, and now here he was. He held the throngs of cops at bay for the next six hours, pressing the barrel of the magnum into his nose and threatening to shoot every time they attempted to get close. Looking at Harrelson's origins, it's hard to believe he ended up where he did. He was born the youngest of six children into a god.

a god-fearing law-abiding family in Love Lady, a small East Texas town. Love Lady's largest employer was the local prison. The justice system loomed large throughout Harrelson's childhood. One of his uncles was a prison warden, while another was a detective in Houston. Several of his siblings were interested in law enforcement too. But not Charles. From an early age, he was more into high-risk, high-reward pastimes. For example, to entertain himself, he used to sit in front of a mirror and practice cheating at cards.

To quote an investigator who knew him as an adult, he had a gambler's personality. Vanessa is going to take over on the psychology here and throughout the episode. Please note, Vanessa is not a licensed psychologist or psychiatrist, but we have done a lot of research for this show. Thanks, Greg. So what exactly does it mean to say somebody has a gambler's personality? A 2014 study at the University of Missouri found that the heaviest gamblers tended to share a fairly consistent personality profile. They showed high levels of aggression and alienation, low restraint, and high levels of sensation seeking. With sensation seekers, it's all in the name.

They tend to crave novel and intense experiences, become bored easily, and have a higher tolerance for risk. If we're right in thinking Harrelson fit this personality profile, it does kind of explain why he struggled to find direction as he grew up. After leaving home at 18, he had a stint in the Navy, but military life surprisingly didn't fit. After returning to Texas, he met and married a woman named Diane. Not long after, Harrelson tried to make a go of it out west, and the couple moved to Los Angeles in 1959. L.A. held just about as much promise as the Navy, which was none at all. Right. It doesn't seem like a career.

materialized for Harrelson there. At least not a legal one. Not long after arriving, he committed a robbery. He also got caught for said robbery and was sent to jail. But he didn't stay there for long. While behind bars, he became a police informant, allowing officers to secretly record his conversations with a fellow inmate. In exchange, he got off with just five years probation. Harrelson was around 21 at this point and eager to start building a life with Diane. Soon after his release, the couple moved back to Texas and lived in the small city of Midland. Over the next few years, they had three children, all boys, Brett, Woody, and Jordan. Woody, like we mentioned earlier, grew up to become an Oscar-nominated actor

who's played his fair share of both cops and criminals over the years. He's talked about his father a handful of times, recalling that his dad wasn't around much. Because if you thought Harrison would try to settle down after having kids, you'd be wrong. He was in and out of prison repeatedly as his sons grew up. Eventually, Diane divorced him and got sole custody of the boys. By 1965, Harrelson was living in Houston and gambling full time, which he seemed to do well at, maybe because he had his own way of playing. Other gamblers said he was good at using sleight of hand techniques to rig games and cheat other players out of money. But it seems like what he really craved more than anything

was the adrenaline rush that he got from breaking the rules. He seemed to thrive on the uncertainty, the highs and lows he got whenever he won big. But the thing was, he wasn't making enough money to offset his losses. It seems like by 1968, he was open to a new kind of hustle. According to most accounts, someone we don't know who, paid Haroldson $1,500, dollars to kill a Houston area carpet business exec named Alan Berg.

A few have speculated that it might have been a former business partner, or gambling debts may have been to blame. Either way, just know that the details of what happened next are sparse. One night, Berg went to a bar and was seen leaving with a mysterious woman. According to Texas Monthly, that was Sandra Sue Addaway. Sandra was Harrelson's new girlfriend. When Berg left the bar, Sandra later said, she led him to Harrelson. the Red Cadillac. Apparently, Harrelson then took off with Bergen's side. Like we said,

there's not a lot of information about this, so we're going to defer to what the prosecutors later said here. They claimed at one point, Harrelson wrapped a rope around Berg's neck, then fired two shots into Berg's head. His body was then left to decay in a grove of cedar trees in Surfside Beach, Texas, about 60 miles from Houston. Berg's family reported a missing soon after. Despite going to the police, and pleading for information in the local papers, they were left without answers for months. If Harrelson really did kill Burke, you might have seen this whole thing as a rousing success.

It came with a big payday, and it didn't initially seem like authorities were onto him. So it should come as no surprise that just two months later, in July 1968, Harrison agreed to do it again. In a moment, Harrelson's second hit. Listeners, in honor of

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The Unsolved Murders special The Missing Dead starts May 16th. Follow disappearances and unsolved murders to hear all of these episodes all month long. Listen free only on Spotify. Are you looking for support in your weight management journey? Zepbound terseptide may be able to help. Zepbound is a prescription medicine used with a reduced calorie diet and increased physical activity to help adults with obesity or some adults with overweight who also have weight-related medical problems to lose excess body weight and keep the weight off. Zepbound is approved as a 2.5,

5, 5, 7.5, 10, 12.5, or 15 milligram injection. Zepound contains terseptide and should not be used with other terseptide-containing products or any GLP1 receptor agonist medicines. It is not known if Zepound is safe and effective for use in children. Don't share needles or pens or readies or use needles. Don't take if allergic to it, or if you or someone in your family had medullary thyroid cancer, or if you've had multiple endocrine neoplasia syndrome type 2. Tell your doctor if you get a lump or swelling in your neck. Stop, zep bound, and call your doctor if you have severe stomach pain or a serious allergic reaction. Severe side effects may include inflamed pancreas or gallbladder problems. Tell your doctor if you experience vision changes before scheduled procedures with

anesthesia if you're nursing, pregnant, plan to be, or taking birth control pills. Taking Zepbound with a sulfonel urea or insulin may cause low blood sugar. Side effects include nausea, diarrhea, and vomiting, which can cause dehydration and worsen kidney problems. Talk to your doctor. Call 1-800-545-99 or visit Zepbounds.lily.com. Now back to the story. In the summer of 1968, Charles Harrison was approached for another contract killing. The client was Pete Scamardo, a local grain dealer who lived,

about 100 miles northwest of Houston. He paid Harrelson between $2,2,500 to kill his business partner Sam DeGellia Jr. So he could collect on a life insurance policy. Harrelson lured DeGellia to a parking lot in a small southern border town by posing as a potential client. At some point, Harrelson shot DeGellia twice in the head. Then he disposed at the body behind a gas station a few miles away. Before moving on, let's take a minute to focus on the fact that Harrelson took a pretty hard turn into killing for cash. Even if he did have gambling debts, surely there were plenty of other less dangerous ways to make a quick buck. In all likelihood, contract killing was not Harrelson's only option. He chose it. Planning and carrying out a hit may have given him an enhanced version of

the thrill he got from gambling, right down to the promise of a huge payout if he's a huge payout if he's he could defy the odds. Earlier we discussed sensation-seeking behavior in heavy gamblers. Dr. Frank Farley, a former president of the American Psychological Association, developed a model known as the, quote, Big T personality to describe a type of person

who's exceptionally drawn to risky extreme endeavors. This personality type can be a blessing or a curse. On the positive side, it can create huge success in fields like entrepreneurship and extreme sports. But Farley noted that the Big T personality also has a dark side. It can drive a person to enormously destructive behavior, including terrorism and violence. Harrelson seemed to be on the dark side of this coin, and his actions were about to catch up with him. Let's go back to the murder of Allen Berg.

Because in the fall of 1968, a few months after DeGelia was killed, police found Berg's remains. The discovery wasn't just a lucky guess. No. It was only made thanks to an informant. Berg's father had paid him $10,000 in exchange for directions to the body. That informant had worked at Berg's carpet business, and, as it just so happens, had begun dating Sandra Sue Addaway. We can only guess she gave him the information after she'd broken up with Harrelson. Police arrested her, and she quickly told them about Harrelson. A few days later, they had a warrant. After being indicted, Harrelson fled the state, hoping to avoid capture. He made it all the way to Georgia.

But his freedom didn't last long. Within days, police tracked him down to a boarding house in Atlanta and arrested him. Within months, he was back in Texas, awaiting his trial. In August 1970, Harrelson had his day in court. So did his former girlfriend, Sandra Sue Addaway, who shared her side of the story. including that she helped pick up Berg at the bar. But two witnesses came forward with an alibi for Harrelson. They claimed he was with them when Berg died 100 miles away.

And in the courtroom, Harrelson was sharp, dressed, and charismatic, charming everybody from jurors to sheriff's deputies. He was also handsome and confident. He made such a splash that newspapers at the time even commented on his looks. His bravado seemed to work, and for a jury looking for reasonable doubt, there was plenty. After only two hours and 40 minutes, they acquitted Harrelson. This was on September 18, 1970.

But he wasn't out of the woods yet. Remember, Harrelson had been involved in another murder for hire. Pete Scamardo had been arrested and convicted of hiring Harrelson to kill Sam Degeliad Jr. that same year. That conviction opened up Harrelson to his own trial, another trial. But when Harrelson went before a jury, they ended up deadlocked. Eventually, the state tried him again in 1974. This time, he was convicted of DeGelia's murder and sentenced to 15 years.

It was around this time that Woody Harrelson learned of his father's crimes. In a 2012 interview with The Guardian, Woody recalled being picked up from school and hearing his father's name on the car radio when a broadcaster was discussing the murder trial. The news shocked him. His mother Diane had understandably tried to shield her sons from the truth. But now, after two murder trials, Charles Harrelson was national news. He was getting a reputation behind bars, too.

A sheriff's deputy who got to know Harrelson in prison was bowled over by Harrelson's encyclopedic knowledge of the Bible. So much so that he nicknamed him Deakin. He said Harrelson was, quote, one of the most well-mannered and intelligent people that I had. ever met in jail. And that pleasantness seemed to pay off. After serving just five years, he was released for good behavior. I'll say it again, five years for premeditated murder. After his release in 1978, Harrelson walked out of federal prison and got straight into a rented limousine, paid for by a young female admirer he'd met during the trial. Not long after, he married a different woman named Joanne Starr, But that commitment didn't seem to be worth the paper it was written on.

Within the year, Harrelson had affairs with multiple women. I mean, he'd been behind bars for years, and now he was back out in the world. Given what we know about his personality, you've got to imagine Harrelson was more restless and unrestrained than ever. He went back to gambling, but it seems that wasn't scratching the itch. He needed a new gig, a new target. And fittingly enough, he found it at a casino. In the spring of 1979, during a trip to Las Vegas,

Harrelson met Jimmy Chagra, an El Paso drug trafficker, about to go on trial in Texas. The judge presiding over the case was John H. Wood Jr. Among criminals, Wood was known as Maximum John, thanks to his reputation for imposing long sentences, especially for drug offenses. You might remember that we mentioned a judge at the beginning of this episode.

The renowned justice that Harold executes. We'll tell you now, Wood is that judge. So just know that this is where things get a little chaotic. Chagra felt like he wasn't going to get a fair trial. While at a casino, Chagra complained to Harrelson that he ought to have Judge Wood killed. Harrelson's ears pricked up. He knew how to do that. So the two men began talking. By the end of the night, Chagra had offered Harrelson the ludicrous sum of $250,000 to kill Judge Wood. To Harrelson, this was a life-altering amount of money, at least a hundred times what he'd made for killing DeGelia. He threw himself into the gig without hesitation. That meant returning to Texas where he spent the next few weeks

stalking Judge Wood, getting to know his daily routine. On one occasion, he tracked Wood down to a federal courthouse in Midland. There, Harrelson watched the judge from the shadow. finger on the trigger of his hunting rifle. He had a clear shot, but something stopped him. Maybe he realized that killing the judge outside a courthouse in broad daylight wasn't the best idea. I mean, Harrison seemed impulsive, but like any gambler worth his salt, he probably knew when to play his hand and when to bide his time,

which came soon enough. On the morning of May 29, 1979, Judge John H. Wood Jr. strolled out of his townhouse in San Antonio and headed towards his car. He had a packed day at the federal courthouse nearby, and his mind was already on the tasks that lay ahead. He didn't notice the man hiding behind his carport. Forty-year-old Charles Harrelson had been lurking there for hours, waiting for the judge to leave for the day. Before dawn, he'd arrived at the property and slashed one of the tires on Wood's car. He wanted to make sure he couldn't get away.

As he watched Wood walk towards the carport, he looked through the scope of his hunting rifle and fixed him in the crosshairs. Then he fired a single round into Wood's back. Wood crumpled to the ground. Taking just a moment to appreciate his perfect shot, Harrelson slipped away from the scene. He'd gone unnoticed, but his crime most definitely hadn't. At first, a few nearby residents figured they'd heard a car backfiring, but they looked through the way. window just in time to see Wood collapse. A neighbor called the police and then sprinted out to where Wood lay in his driveway. He had no pulse. Any murder in broad daylight would be headline news,

but when the police arrived at the scene, they soon realized they were dealing with something even bigger. The first murder of an American judge in the 20th century. Within minutes, a sprawling investigation was underway. Up next, Harrelson goes into a downward spiral. Episode is brought to you by Prime. Obsession is in session. And this summer, Prime Originals have everything you want. Steamy romances, irresistible love stories, and the book to screen favorites you've already read twice. Off campus, L, every year after, the love hypothesis, Sterling Point, and more. Slow burns, second chances, chemistry you can feel, through the screen. Your next obsession is waiting. Watch only on Prime.

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to actually follow through. To Chagra, it was a simple misunderstanding. a joke at a card table that may have gone too far. As a veteran drug trafficker, he probably had some idea what a professional criminal looked like, and Harrelson wasn't it. He hadn't even given Harrelson the money. Chagra's case was the most high profile on Woods Docket for that week. With the judge now dead, Chagra knew he'd be under scrutiny. He was right.

The FBI quickly zeroed in on Chagra as the puppet master of the hit, and it was a good thing for them that Chagra. actually ended up going to jail on his original drug charge. Exactly. This gave the authorities a golden opportunity. While Chagra was behind bars, the feds were able to tape hours of conversations between him and his fellow inmates, in which he admitted to having Judge Wood assassinated.

Based on those recordings, they got permission to surveil the entire Chagra family. During this period, they briefly identified Heraldson as a suspect. For some reason, they cleared him. That left Harrelson free on the streets, but once again, it didn't last long. Sometime in 1980, Harrelson was arrested in Houston on drug and weapons charges after being found with cocaine and loaded dice in his car. You'll never guess who he called to help him stay out of prison. Joe Chagra, Jimmy's older brother.

Joe was a lawyer in El Paso, and he had at least one significant thing in common with Harrelson, a cocaine habit. As you may have already guessed, this arrangement was a terrible idea. For months now, the FBI had taped Jimmy Chagra's conversations in prison and had recordings in which he confessed to having Judge Wood assassinated. They still had no solid leads on who exactly had pulled the trigger. But now, with Joe Chagra acting as Harrelson's attorney, there was a link between Jimmy Chagra and a convicted hitman.

Harrelson found himself back on the suspect list. That July, Harrelson skipped his court date on the drug charges in Houston. He needed to lay low, and he found a great place to do it. While in hiding, he stayed at a house owned by Virginia Farah, an heiress who'd previously hired him as a bodyguard. But despite the plush setup, the paranoia being pursued, coupled with his use of cocaine, was a recipe for disaster. Over the next few weeks, Harrelson began losing touch with reality.

He became convinced that DEA agents were watching him from the trees outside his window and crawling through holes in his bathroom wall. It seems Harrelson may have been experiencing cocaine-induced psychosis. Paranoia is common in psychosis. People often develop persecutory delusions, where they believe they're being pursued by shadowy forces. The content of delusions can change a lot depending on the cultural context, so someone raised in a religious family may be more likely to believe

the devil is trying to possess them. On the other hand, in someone from a secular background, delusions might manifest as the government trying to control them. In Harrelson's case, it's easy to see why federal agents were the source of his persecution. But as the old saying goes, it's not paranoia if they're actually out to get you. Harrelson really was a wanted man, and unfortunately for him, his mounting fears and detachment from reality made him a terrible fugitive. Eventually, he couldn't bear to spend one more minute trapped inside. Which brings us back to September 1980 on that Texas stretch of highway. Before the police standoff, Harrelson was speeding down the I-10 on the outskirts of a small Texas town called

Van Horn, trying to escape imaginary FBI agents. Their faces seemed to be bursting out of every highway sign. There was a rattling sound coming from his car's muffler, which, set his teeth on edge. As he drove, the noise seemed to get louder and louder. He pulled over on the shoulder, got out, and began shooting the back of his car. Then for reasons known only to himself, he pointed the gun at his own head. Within moments, police arrived at the scene, called thereby alarmed motorists. Inadvertently, Harrelson had turned himself in, or maybe it wasn't an accident. After all, Harrelson had the instincts of a lifelong gambler. He knew when to fold them.

Over the six-hour standoff that followed, it sure seemed like Harrelson was doing all he could to incriminate himself. Though he refused to surrender, he confessed to killing not only Judge Wood, but a whole host of other people, including President John F. Kennedy. The FBI didn't find that particular confession credible. The standoff finally ended when the police,

called Virginia Farah, the heiress whose house Harrelson had been holed up at. She came to the scene and persuaded Harrelson to surrender. Once he did, the cop searched his car and found about eight ounces of cocaine, along with unlicensed weapons. They booked him on drugs and weapons charges, taking him into custody in Harris County, Texas. He pleaded no contest and was sentenced to 40 years in prison. Even though he was behind bars, authorities still wanted to peer to. him for Judge Wood's murder, and honestly, Harrelson seemed happy to help out with that. Even after the cocaine-induced psychosis dissipated, he appeared to be determined to prove that he'd killed Wood. Maybe he was proud of himself or wanted glory? Whatever the reason,

it outweighed any instinct for self-preservation. While he was in custody, he told prosecutors he knew something about the Wood crime scene which had never been revealed to the public, something only the killer would know. One of Wood's tires had been slashed right before the murder. The investigation gets pretty convoluted at this point. There was Harrelson's confession, along with various agencies piecing together all the other evidence. But ultimately, the FBI found the murder weapon and linked it back to Harrelson. That did it.

In April of 1982, 43-year-old Harrison was indicted for killing Judge Wood. He got two life sentences for the crime. Harrelson's impulsive and reckless behavior had finally backed him into a corner he couldn't get out of. Not that he didn't try. In the summer of 1995, just days before his 57th birthday, he made an escape attempt. He and two fellow inmates tried to climb over the prison wall using a makeshift rope. Yeah, they didn't make it out. His other attempted escape looked a little different. Despite his numerous self-incriminating statements, he officially recanted his confession in 2003.

He claimed somebody else had assassinated Wood. His son Woody, who by this time was an internationally famous actor, tried for years to get his father a new trial. He said, quote, I'm not saying that he did or didn't kill the judge. I'm just saying he didn't get a fair trial, end quote. But in the end, those efforts went nowhere. and Charles Harrelson died of a heart attack in 2007 at the age of 68. He never spoke publicly about his crimes, but the FBI did retrieve a note that was apparently written by him before his death.

It apologized for the pain he'd caused his own family and the families of his victims, but concluded by saying, quote, I've never killed a person who was undeserving of it. As far as the official record goes, Harrelson killed only two people, Sam Degalia Jr. and John H. Wood Jr. and he made between $3,500 and $4,000. It's not exactly a career. At most, it's a side hustle. But is this really that unusual? I'm wondering if the archetype of the highly polished professional contract killer is just something we've all collectively picked up from movies rather than the norm. Some of the best data we have on this comes from the UK.

In 2014, David Wilson, a professor of criminology at Birmingham City University, published a huge study on the recent history of contract killing. We touched on this briefly in our other hitman episode, The Killer Brothers, but basically Wilson identified four main types of contract killers. Out of these four, Harrelson probably falls into the novice or dilettante category. Both are less experienced, less committed to the work, and tend to take on contracts out of necessity, like when they need to resolve a personal financial crisis.

It reminds me of something we've talked about on the show before, about the stereotype of the genius serial killer who constantly outsmarts law enforcement, and how it's largely a myth. Only a small percentage of serial killers are unusually intelligent, just like the general population. The same goes for the highly professional contract killer, As is so often true in life, the reality is a lot messier than the myth, but also some might say more interesting.

Thanks again for tuning in to serial killers. We're here every Monday and Thursday. For more information on Charles Harrelson, amongst the many sources we used, we found Gary Cartwright's 1994 article in Texas Monthly, The Sins of the Father, extremely helpful in our research. You can find all episodes of serial killers and all other sources. Spotify originals from Parcast for free on Spotify. We'll see you next time. Stay safe out there. Serial Killers is a Spotify original from Parcast. Our head of programming is Julian Boarrow.

Our supervising sound designer is Russell Nash, with Nick Johnson as our head of production and Spencer Howard as our post-production supervisor. Stacey Nemek is our supervising editor and Derek Jennings is our writing lead. This episode of Serial Killers was written by Emma Dibdin, edited by Robert Tyler Walker and Kate Murdoch, fact-checked by Catherine Barner, researched by Brian Petrus and Chelsea Wood, produced by Bruce Kitovich, and sound design by Michael Motion. Our hosts are Greg Poulson and me, Vanessa Richardson.

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