Death of a Gambler
Death of a Gambler
“Comic book store owner shoots, kills armed robber in self-defense,” ran the headline from Chicago’s Daily Herald in November 2006. The kind of small-scale tragedy you read about every day. But neither the headline nor the article below hinted at the lifelong problem that lay behind the event.
I came to federal prison in 1993, a 22-year-old suburbanite with a 25-year sentence for a first-time LSD offense. I was shipped to FCI Manchester, a medium-to-high security prison in the foothills of Kentucky. Movies had prepared me for the worst. But luckily they didn't throw me in with a big guy named Bubba. My first cellie was an average looking dude from Indiana, a few years my senior. His name was Geoffrey Webb.
"How you doing, buddy?" he greeted me. "Where you from? How much time you doing?" Mild-mannered and respectful—with no tattoos, bulging muscles or Old West mustaches—he made it seem more like arriving at a college dorm than prison. Like me, Geoff had grown up in the suburbs. He was a dedicated Colts fan, and loved to play basketball.
Everyone on the compound came to our cell for tips. Geoff was the authority on which horses to bet on, and would dispense his wisdom liberally.
I threw my stuff on the upper bunk and gave an inward sigh of relief.
As I settled in, I learned Geoff’s story. He had a 12-year sentence for bank robbery. But to hear him talk, he was a professional gentleman robber along the lines of Jesse James. He’d meticulously planned his heist, tracking the bank manager’s movements and following him home, in order to kidnap him at gunpoint, take him back to the bank and make him open the vault. This was all done—according to Geoff—in the most considerate way. It was a big score for him: several hundred thousand dollars, which the cops never recovered.
You hear plenty of tales in federal prison, but what stands out about his was the reason he robbed the bank in the first place: to pay off big gambling debts. He gambled on everything—sports, cards, games—but his main vice was the races.
Before he robbed the bank, he was so deep into the race scene that he’d even bought some horses, stabled and trained them, and entered them into events. He loved them so much that he bet on them every chance he got, even when they kept losing, again and again. Geoff had faith; he was the type of gambler who thought he could win every bet. But his luck never turned.
He got in serious debt, wore out his welcome with family and friends, and seemingly had no way out—so he pulled off the robbery and paid back the money he owed. "I just did what I had to do," he told me. "I didn't think I would get caught."
As the months went by, we got more comfortable in our environment and started venturing out to the yard more. And that’s when Geoff jumped into the illicit gambling scene that thrives in every prison. Parlay tickets, over-unders, straight bets, freeze outs, 10-pick teasers, poker, spades, tunk, pool games, shooting contests—he did it all.
He was always first out of the cell in the morning when the doors cracked—coffee cup in hand, eyeing SportsCenter—and the last to leave the TV room at night, so he could check his tickets and see if he hit.
Out on the yard, I’d see Geoff holding court at the poker game or going over odds and spreads with other gamblers as they scoured the sports schedules. "This game is a lock," Geoff would tell me. "You got some stamps to put on it?"
When he came back to our cell in the evening, I could tell instantly if he’d won or lost. When he was flush he had a glow about him; it would be sodas and nachos, a small celebration to break the monotony of prison life. "You ready to eat?" he would ask. "My treat."
If he lost, he would go right to bed, not wanting to talk. He’d bounce back the next day, depending on how much he’d lost, but it would always take him the night to recover.
Still, a lot of prisoners do their time like that: Betting brings hope of the big score and all the buzz of sweating tickets, glued to the bottom line on ESPN.
Geoff kept me interested, too. He used to get all the race papers and try to explain handicapping and betting on the horses to me. "You gotta learn about this stuff," he would tell me. "You can get rich off the horses." He got horse breeding magazines and knew all the breeds. When the big races like the Triple Crown came around each year, he would be amped up, predicting the winners. Everyone on the compound came to our cell for tips. Geoff was the authority on which horses to bet on, and would dispense his wisdom liberally. He was a historian too: He could tell you who won what in any year.
During lockdowns he would scan AM radio stations for sports news, so he could get an edge. Geoff recited odds and over-unders and won-loss records like other prisoners spit rap lyrics; he had it all in his head.
Besides the Triple Crown races, football season was his favorite time: From late August until the Super Bowl, Geoff would be filling out multiple parlay tickets, betting on every game he could. He bet on which team would score the first field goal or touchdown, and even played quarter boards. He would gather his stamps every weekend, borrowing whatever he could, sweating each and every ticket until it was dead.
Eventually he started running tickets for other dudes on the compound and even opened his own—named “Triple Crown,” of course. He enlisted me as a runner and we used to hold the stash of stamps that were bet on his ticket in our cell. One time we got busted with 125 books and sent to the hole for a couple of weeks. As soon as we got out, Geoff was back at it with a vengeance.