Andrew Rizzo’s family has owned the same piece of Chicago property next to Wrigley Field since 1946, when the family immigrated to the U.S. from Italy and opened Cubs Park Service Station. That business turned into parking for Bears and Chicago Cubs games until, in 2017, the family opened Rizzo’s Bar & Inn.
Like many bars in Wrigleyville, a significant portion of Rizzo’s revenue comes during baseball season, and a deep playoff run can seriously shift margins. Bars are packed, and because playoff tickets are more expensive, the bar often hosts wealthier clientele who spend more money. An early postseason exit, however, can mean unrealized revenue.
So as the Cubs squeaked their way into the postseason, Rizzo traded $7,500 on Kalshi that the Cubs would host two or fewer home playoff games. He hoped, both as a Chicagoan and businessowner, that he would be wrong.
