The Crosstown Classic

Two attorneys reflect on their Cubs and Sox fandoms

Published in 2024 Illinois Super Lawyers magazine

By Josh Karp on February 1, 2024


Matthew O’Malley (right) is a Southsider through and through. After growing up on 84th Street, then living in Palos Heights, he has settled down and is raising a family on the South Side—all of which means one thing: He’s a tailor-made White Sox fan.

“I feel like, with Chicago baseball, you really don’t get to pick your religion,” says O’Malley, a litigator with Tressler. “You’re just born and raised into a team.”

Ironically, O’Malley’s paternal grandparents came from Ireland and settled on the North Side, where his father grew up as a Cubs fan. That all changed, however, when he met O’Malley’s mother, who came from Bridgeport and a tradition of rooting for the Sox.

Thus, the team has always been a huge part of O’Malley’s life. “I remember following the Sox during the Frank Thomas days, going to the ballpark and getting Italian ices with my grandparents,” he says. “I had to have been a toddler for my first game.”

O’Malley’s happiest baseball memory, of course, was staying up late in 2005 to watch Game 4 of the World Series, when the Sox beat the Astros 1-0 to complete the sweep. Several of his favorite players ever were on that team, including Paul Konerko, Jermaine Dye, and A.J. Pierzynski.

“I remember we didn’t have a TV in our bedroom, so we pulled our basement TV up to watch the games. It was a special season,” he says. “On the day of the parade, half of my school didn’t show up. We didn’t go, which is a regret. I was one of the schmucks at school.”

The following year, O’Malley’s parents bought season tickets—which he says may have cursed the team, as the Sox have made just three of the past 18 postseasons. “Stop buying the tickets,” O’Malley recalls telling them. “You’re the jinx now!”

Regardless of how a season shakes out, O’Malley remains a diehard fan, anticipating the next opening day. “I think this season was a big letdown because there was so much potential,” he says. “But I take a lot of pride in being from the South Side, and I still love my Sox. There’s always next year.”

Ashley D. Jaconetti (second from right) grew up in Park Ridge and has roots on the North Side: Her grandparents had season tickets on Wrigley Field’s third baseline.

“I always remember being a Cubs fan,” says the litigator with Dershow Law Group. “It was always so fun, and such a treat, to go to a game at Wrigley.”

Jaconetti and her three younger siblings would paint their faces or wear funny hats to get on TV at games. “I was 4 when I went to my first Cubs game,” she says. “You just get a feeling like you’re at home or in your neighborhood. There’s an energetic environment there.”

Over the years, she’s been at Wrigley for numerous Sammy Sosa home runs, and one April game that was so cold the family wore winter clothing. “We stayed all game, and we have the pictures to prove it,” she says.

In 2003, Jaconetti watched the Cubs get within five outs of making the World Series, only to end up bowing out of the postseason. It was a low point erased 13 years later, in 2016, when the Cubs defeated Cleveland in seven games to win their first title since 1908.

“I was at home, on the couch, and I remember how intense it was: We would switch our seats to find which was lucky, and we kept getting closer and closer to the TV,” she recalls. “But it was great to be in the city when it finally happened. You could feel the positive energy.”

In the years since, Jaconetti has watched the Cubs trade away key players like Anthony Rizzo, Kris Bryant, and Javy Báez, but she is enthusiastic about the new group of players the team has assembled. “They have a great team this year,” she says. “I’m pretty optimistic.”

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Ashley D. Jaconetti

Ashley D. Jaconetti

Top rated Civil Litigation lawyer Dershow Law Group, P.C. Chicago, IL
Matthew O'Malley

Matthew O'Malley

Top rated Civil Litigation lawyer Tressler LLP Chicago, IL

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