There’s a long standing friendly wagering tradition between newsrooms when big games like the World Series happen to land in their respective cities.
If you haven’t heard, the Tampa Bay Rays will take on the Milwaukee Brewers in the World Series. In a sport dominated by big money two mid-market teams are on center stage and the match-up promises to be rollicking baseball. Neither franchise has ever won a world championship.
Recently, our fearless editor Mark Katches reached out to his good friend and former colleague Greg Borowski, executive editor of the Milwaukee Journal Sentinel, and made a friendly bet.
Hard Rock nor Kalshi mediated this wager.
If the Brewers win, we’ll ship them some La Segunda Cuban sandwiches, Katches said Friday morning before Game 1 of the World Series. If the Rays win, they have to send us Real Chili, which is an iconic little chili shop in Milwaukee.
“I would have chosen Wisconsin brats, cheese curds or custard to put up for the bet, but I didn’t want to stand in the way of Mark’s love for Real Chili,” said Borowski Friday afternoon by email. “That’s OK, because the Brewers are standing in his way.”
Real Chili is an almost century-old diner near Marquette University in downtown Milwaukee, Wisconsin. In the tradition of Green Bay chili parlors spicy meat over noodles and beans, Francis Honish opened the spot in 1931. The chili comes mild, medium and hot.
Real Chili is a five-alarm affair, Katches said.
Sometimes the stakes are food and sometimes they are cartoons and editorials. For Super Bowl LX last year the Boston Globe and the Seattle Times wagered a cross country cartoon and editorial exchange.
“It’s been a tradition that dates back decades. It doesn’t happen every year, or in every sport. But it still happens,” Katches said. “And it’s mostly driven by editors who know each other in the cities involved.”
COVID kind of put a kink in the tradition for the Tampa Bay Times’ newsroom. For Super Bowl LV in 2020 when the Bucs defeated the Chiefs “we didn’t even cross our minds,” Katches said. “Or when the Rays played the Dodgers in the World Series bubble or [when] the Lightning were winning back-to-back Stanley Cups.”
“Which is a shame because we could have won way more bets than we would have lost back then,” he said.
The chili, if the Rays win (in six, just saying), might come with a bottle of Tums, alleged Borowski.
When Katches was the deputy managing editor at the Journal Sentinel at the tail end of the aughts, he said he’d try to squeeze in a Real Chili lunch at least once a week, until his cholesterol spiked.
“In the unlikely event that the Brewers win, I’ll also throw in a bottle of Vitamin D. They’re going to need it for the cold, dark months ahead,” Katches said. “It’s the next best thing to sunshine, I guess.”
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