Featured Story, Prison Stories

A Troubled Mind: The Life and Crimes of a Gambling Addict

I came to federal prison in 1993, a 22-year-old white suburbanite with a 25 year sentence for a first-time, non-violent LSD offense. I didn’t know what to expect as I was shipped off to FCI Manchester, a medium-to-high security level prison in the foothills of Kentucky. From all the movies I had seen I was prepared for the worst, but when I arrived, luckily they didn’t throw me in the cell with a big black guy named Bubba. My new cellie was an average looking white guy from Indiana a few years my senior, his name was Geoffrey Webb.

Geoff was a mild-mannered, respectful and considerate dude. “How you doing, buddy?” He greeted me. “Where you from? How much time you doing?” He made it seem more like arriving at a college dormitory than prison. I learned that similar to me Geoff had grown up in the suburbs. He was from Indianapolis, a dedicated Colts fan and loved to play basketball and other sports. He was far different than what I expected a prisoner to be- no tattoos, bulging muscles or Old West mustaches- but I guess in a lot of ways, so was I. As I threw my stuff on the upper bunk and made my bed I gave an inward sigh of relief. Maybe all the horror stories I had heard about prison weren’t true. With the long bid I had to do I was hoping my luck would hold true. Geoff became a close friend and my first cellmate in federal prison.

As I settled in and got to know Geoff his story was related to me in bits and pieces. He had a 12 year sentence for robbing a bank. But Geoff was not your typical run-of-the-mill bank robber. To hear him describe it, he was a professional gentleman robber along the lines of Jesse James. He had meticulously planned his heist, tracked the bank manager’s movements and followed him home from work to politely kidnap him, take him back to the bank and make him open the vault. This was all done in the most considerate way he could do it, according to Geoff. It was a big score for him, over several hundred thousand dollars, which consequently was never recovered. You hear all kinds of stories like that in federal prison, but what makes Geoff’s different was the reason he had robbed the bank in the first place.

Geoff had a severe gambling problem. He gambled on everything- sports, cards, games, stats- but his vice was the races. Geoff was so deep into the race scene that he had even bought some race horses, stabled and trained them and entered them into events. He loved his horses so much that he bet on them every chance he got, even when they continued to lose, again and again and again. Geoff had tremendous faith in his horses and his gambling acumen. He was the type of gambler who thought he could win every bet. He figured the odds were in his favor and that his luck would turn, but it never did. Geoff got in serious debt, wore out his welcome with family and friends, and seemingly had no way out until he concocted the bank robbery plan, put it into action and paid off his gambling debts. “I just did what I had to do,” he always told me. “I didn’t think I would get caught.” But the end result was a 12 year federal prison sentence for bank robbery. A high price to pay for a gambling addiction, but one Geoff was forced to endure.

Most people would do some soul searching and maybe admit that they had a problem after losing their freedom due to gambling but not Geoff. This is typical of gambling addicts, who can appear normal in every way except that they gambled their way into a bottomless pit. The financial devastation they can wreak is not so readily apparent in outward appearances. As the months went by and we got more comfortable in the prison environment we started venturing out to the yard more, and as Geoff reached a comfort zone he jumped into the avid gambling scene that thrived at the prison- parlay tickets, over-unders, straight bets, freeze outs, 10-pick teasers, poker games, spade tournaments, tunk, intramural sports, pool games, shooting contests- Geoff did it all and bet on everything he could. He was always first out of the cell in the morning when the doors cracked, hot coffee cup in hand, catching the scores on Sportscenter and the last to leave the sport TV room at night so that he could check all his tickets and see if he hit. At the time I didn’t think anything of it, it was just what Geoff did. A lot of prisoners did their time like that, gambling on sports and playing cards. Prison is full of gambling aficionados. Betting gives prisoners hope and opportunity for the big score, and all the excitement that goes along with it, it’s like a buzz as they sweat their tickets, watching the games and seeing the scores come in. They’re glued to the bottom line on ESPN, with the mindset that they’re one bet away from winning everything back.

I would be out on the yard and see Geoff holding court at the poker game or going over odds and spreads with the other gamblers as they scoured the schedules looking for that lock, that game they could win big on. “This game is a lock,” Geoff would tell me. “You got some stamps to put on it?” I could always tell when he came back to the cell if he won or lost by his mood. When he was flush with winnings he had a glow about him and it would be sodas and nachos, a small celebration to break the dull monotony of prison life. “You ready to eat?” He would ask. “My treat.” But if he lost he would be distraught and go right to bed, not even really wanting to talk at all. The overwhelming urge to vanish, to remove himself from the world would prevail. He would bounce back the next day, depending on how much he lost, but it would take him the whole night to recover. As I look back now, in retrospect, I can see he exhibited all the signs of a chronic gambler, but in the moment I was more concerned with myself and my own issues in dealing with a 25 year drug sentence as a young man. But all the signs were there for Geoff- anxiety, anger, paranoia, impulsiveness, preoccupation- I just put it down to the stress of doing time.

We had some all right times, though. For prison at least. Geoff used to get all the race papers and try to explain handicapping and betting on the horses to me. He was really into it. “You gotta learn about this stuff.” He would tell me. “You can get rich off the horses.” He got horse breeding magazines and knew the different breeds of horses and was deeply passionate about them. When the Kentucky Derby and other horse races came around every year he would be amped up, predicting what horses would win, and everyone on the compound came to our cell when they wanted to know anything at all about horses. Geoff was the authority on that and on which horses to bet on for the Triple Crown. He would dispense his wisdom liberally. On the subject of horse racing Geoff was not only an expert but a historian also. He could tell you who won what race and in what year. Horses were his passion.

During lockdowns he would scan the AM radio stations searching for scores or any type of sports news he could hear so that he could get an edge on whatever game was played that night. He would break it all down to me about why and how a team would beat another. He was like an ESPN analyst in that way. Geoff recited odds and over-unders and won-loss records like other prisoners spit rap lyrics. He had all that information in his head, memorized, and easily available for instant recall. And football season was his favorite time of the year, besides the Triple Crown races. From late August, until the Super Bowl in February, Geoff would be in his element, filling out multiple parlay tickets every Saturday and Sunday, betting on every game he could. He took it to the extreme, like which team would score the first field goal or touchdown, and even played quarter boards. He would gather all his stamps every weekend, borrowing whatever he could and play tickets, sweating each and every one until it was dead.

Eventually he started running tickets for other dudes on the compound and even opened his own, which he called Triple Crown of course. He enlisted me as a runner and we used to hold the multitude of stamps that were bet on his ticket every weekend in our cell. One time we even got busted with 125 books of stamps and got sent to the hole for a couple of weeks, but once we were back out on the compound, Geoff was right back at it with a vengeance. I always knew he went hard on gambling, but now I understand the truth- Geoff was a full blown gambling addict. He had no control of his addiction, it was raging out of control and the prison environment we lived in fostered, cultured and supported his addiction. They offered drug education and had Narcotics and Alcohol Anonymous meetings, but there were no gambling addiction programs and even if there were, Geoff wouldn’t have addressed his problem. He didn’t think he had a problem. He liked to gamble. It was his muse.

I always liked Geoff, he was a good dude. I don’t know how he was on the street, but in the cesspool of prison he was kind, considerate and I could trust him to watch my back. That’s more than you can ask for in the netherworld of corruption and violence. We had a lot of good times, as good as they can be in prison, playing basketball, softball, talking about and watching sports, learning to live in the harsh and oppressive world of prison and making the best out of our fucked up situations. Eventually I transferred from FCI Manchester to another prison, FCI Beckley in West Virginia. I kept in touch with Geoff over the years through letters and mutual acquaintances, who we would run into over the years, during transfers or arrivals at new prisons. I know Geoff stayed the same, because every time I saw a mutual acquaintance, they told me how he was still going hard on the gambling tip. We even played in a play-by-mail fantasy football league together for years and made trades and stuff like that, coordinating our season plans and draft strategy through letters. That was just how we did our time. “Gearing up for the football season.” He wrote to me. “You know I got to get my stamps up.”

Geoff always paid his own way though. Even when he was running up gambling debts that exceeded his annual income. He didn’t receive any support from his family financially or morally. They had disowned him when he was convicted and sentenced to prison. I guess Geoff had burned all his bridges, but despite his gambling addiction, Geoff was a hardworking, responsible prisoner. A model inmate really. He never got in trouble or did anything wrong besides gambling that is. He paid his debts, had a good reputation inside the system and always had a top grade position in the prison working as a clerk in facilities or in the factory. I remember at FCI Manchester he would file all the paperwork, do the reports, pay roll and all the memos for his boss, the facilities manager. Geoff made himself very useful in that regard. For prison, Geoff made very good money. But he never got help or received any treatment for his real problem, even after all the years spent in prison. It was ever identified by anyone. Eventually he was released after serving his time.

Years later, I received an email on Facebook from a mutual acquaintance who had done time with us. This acquaintance was Geoff’s homeboy from Indiana who used to play sports and hang with us in our little crew at FCI Manchester. He had friended me previously and we exchanged pleasantries. But then he hit me the news, “You heard about Geoff, didn’t you?” He wrote. “No, I haven’t. What happened with him?” I responded. “He was shot and killed in a robbery attempt.” He answered. I was flummoxed and still couldn’t quite make the connection as I stumbled in my response. “In Indianapolis? They were robbing his home? That is tragic, yes?” But I was off base in my assessment and dude corrected me. “In Illinois. Geoff was attempting to rob a coin store and the guy behind the counter pulled a gun. Shots were fired and Geoff got shot in the head.” Dude clarified. I was stunned.

I got my wife to do an Internet search and she found the newspaper articles that reported on Geoff’s death and sent it to me. Comic Book Store Owner Shoots, Kills Armed Robber in Self-Defense, the Daily Herald headline read on November 4, 2006. At 10:30 a.m. on a Friday morning, Geoff had entered a cards, comic and coin shop at a strip mall in Roselle, a quiet suburb outside of Chicago and attempted to rob it by brandishing a revolver at the store owner. But the owner pulled his own revolver, shots were fired and Geoff was killed. The articles make Geoff look like an armed robber, a federal prison parolee, but he was more than that. I know Geoff, he wasn’t a violent person and wouldn’t have fired the gun in the robbery, but when the store owner fired on him, what choice did Geoff have?  Geoff wasn’t a violent, armed robber. He was a sick, desperate man, done in by his addiction.

I later found out that Geoff was up to his old tricks. He had gotten into debt again from gambling on the horses and was trying to raise the money to clear his name and debt. Like I said before the man always did pay his debts. But by constantly trying to avoid catastrophe, he compounded his problem with every attempt at a solution. As Geoff’s problem progressed he became more deceitful, manipulative and secretive. I am sure no one knew about his problem and left unchecked, feelings of hopelessness and helplessness must have overwhelmed him. I would have never thought Geoff would resort to crime again. He always seemed like such a nice, mild-mannered dude to me, but I guess he did kidnap a bank manager, no matter the spin he put on it, so go figure. At the time I wondered why he would go to such extremes after all the time he did, but in reality, I know why. I have known it all the time. It’s because he was a gambling addict and eventually his addiction cost him his life. I wish he could have done something with his life besides that, but without help or treatment he never really had a chance. The National Council on Problem Gambling has estimated that one in five gamblers attempt to kill themselves, about twice the rate of other addictions and fewer than five percent of problem gamblers enter into treatment. Without help the extent of their behavior can lead to death, which in Geoff’s case was just another form of self-annihilation, the same as suicide.

Geoff was as normal as could be in appearances and actions, his crimes besides the point. He was a courteous, respectful, agreeable, smart, capable, hardworking and pleasant person to be around. But just the same, he struggled with his inner demons that manifested themselves in his gambling addiction and that addiction led to his life of crime and eventually to his death. His autopsy report didn’t cite gambling as a cause of death, but his addiction killed him just the same as the bullet that ripped through his skull. It’s sad that it has taken all of this for me to realize the truth of the matter. And sadder still that Geoff probably never realized the truth or extent of his own addiction or that he was even an addict at all.

He sent me a few letters when he got out, saying he was working and trying to get his life together. “It’s great to be out.” He wrote. “Now, I can really live again, finally.” This was around 2006. I was happy for him. I figured he would do OK and make it. With his work ethic it was a no brainer. Because for real, despite his bank robbery, Geoff didn’t even seem like a criminal to me. He wasn’t on all that macho, tough guy prison bullshit so many guys are on. But I failed to take into account his gambling problem. In fact I completely dismissed it. I didn’t’ see it as a problem. It was just something he did. I just didn’t make the connection between gambling, his crime and addiction with Geoff. I thought he had it under control. Eventually Geoff stopped writing. After close to 12 years of communication, I didn’t hear from him anymore. But he was out of prison, so I figured he was moving on with his life. But I was wrong.


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