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The Underground World of Bowling League Gambling

You might be borrowing shoes, but if you’re playing the game right, you’re also taking home cash

When Connor joined a bowling league last year, he didn’t realize that also meant he would soon become a gambling man. But for the 33-year-old Chicagoan, walking into Diversey River Bowl that first time was like walking into a casino full of guys drinking in their socks.

For Connor and his three-man team, it started with a $5 poker buy-in, where the cards were doled out between two competing teams, one card for every strike or spare for a hand that would be played at the end of each game, usually with three games and hands per night, totaling only about $90 of potential earnings. “​​Weirdly, the person with the most cards rarely won,” he tells me. “Honestly, it made it like 1,000 times more fun.”

Connor’s dip into gambling resembled a sort of a wholesome homage to the days of “action bowling” — a high stakes form of gambling in 1960s New York where gangsters could walk out of a bowling alley with over $7,000 in cash. Today, gambling on bowling happens in cities all over the country. And in Connor’s bowling league in Chicago, the stakes may not be so high, but the betting is expansive. From team brackets to guessing your bowling score, the one thing all the “side games” have in common is that there’s money on the table — and sometimes even in the lane. 

For example, there are raffles like “strike pot,” where players put their name in the pot for $1, and each week, a bowler is picked to shoot a strike. If they miss their shot, the pot rolls over to the following week, often adding up to hundreds of dollars. “They literally poured out the backpack of ones in front of the lane, so you had to bowl over the dollar bills to win it,” says Connor, recalling one particular pot that was around 400 bucks. Adding to the chaos, bowlers and spectators can do pretty much whatever they want to distract the contestant, from screaming in their ears to dropping a bowling ball right next to them. “My buddy got picked twice and gutter balled it both times,” he says. 

Among the most common and traditional types of gambling within bowling leagues involves placing bets on individual matchups of bowlers in different brackets throughout the night, pinning their scores against one another regardless of whether or not their teams go head to head. And in more complex and lucrative gambling games, bowlers are matched up for double bets in these brackets, where their handicaps are figured in for higher odds and bigger paydays. (Handicaps are roughly based on the difference between the best average score of the best player in the league, and the best average score for that bowler.)

But with the higher stakes, doubles betting can get heated quickly. When bowlers with high handicaps perform well by chance, they can be accused of “sandbagging,” a form of hustling. David, a 38-year-old bowler who’s been knocking down pins since he was five, had a higher handicap in his adult league than his experience would suggest, so he’s been accused of sandbagging more than once. “That’s usually when you’d have a few words in the parking lot,” David tells me. “There’s money on the line, but it’s crazy how seriously a lot of these guys take it.” That said, the Chicago native, who insists he is not a sandbagger, has never had to deal with anything more than verbal altercations.

The most money Richard, another Chicago player, has ever bowled for was around $850. He and his four teammates would all put in $5 before guessing their final score for the game, which had to be above 200. “If anyone hits their score exactly, you get the pot, if not, it gets added on to the next game,” the 47-year-old explains. Given the amount of luck required to hit that exact number, there was a lot of rollover, sometimes over the course of multiple seasons. 

After bowling in leagues in Chicago and New York for 15 years, Richard has found that New Yorkers take the sport itself more seriously, whereas “in Chicago we definitely had a lot more side bets and there was a lot more emphasis on drinking and having a good time.” 

To that end, on Connor’s team of mostly new bowlers, a player must buy a round of shots for every double gutter ball. Meanwhile, David’s more experienced bowling team will often place a “5-pin bet” to get the drinks flowing (in bowling, the fifth pin is a bowler’s nemesis). As David explains, if you “hit the pocket, the 5-pin is supposed to explode.” So when it’s left standing, “people lose their shit.” When this happens, his teammates will raise their hands, signaling they want in on the bet — a $1 buy-in against him picking up that next shot. Say 20 people raise their hands, if David gets the fifth pin on his second throw, he gets the $20. But if he misses it? He has to buy 20 shots. 

Sure, the math doesn’t add up, but that’s what makes it a gamble. And even if he loses a little money, the gambling is never serious enough that he has to worry about losing his (bowling) shirt.