From the South Side to the North Side: Cubs Trio Relish New Chapter in City Series
You can feel it in the air—City Series weekend in Chicago. The rivalry between the Cubs and White Sox might not divide the entire baseball world, but in this city, it’s personal. And for three former White Sox players now donning Cubbie blue—Chris Flexen, Nicky Lopez, and Brad Keller—it’s more than just another series. It’s a full-circle moment, a chance to experience the storied Crosstown Classic from the other side.
Chris Flexen, now a starter for the division-leading Cubs, knows the energy of Wrigley Field all too well. He pitched against the Cubs in this rivalry last year while wearing a White Sox uniform. Even though he threw a gem—one run on six hits over nine innings—his team couldn’t pull out a win. Now, he’s back in that same ballpark, but the cheers are for him this time. “You really see the city show up for both teams,” Flexen said. “But that blue... it just hits a little harder in the stands.”
For Flexen, last year was rough—leading the Sox in innings pitched but ending the season with a 4.95 ERA and 121 team losses. This year, the vibe has completely flipped. With the Cubs contending, the expectations are higher, but so is the focus. And he’s embracing every bit of it.
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Nicky Lopez, a Naperville native, also made the switch. After a tough 2024 defensively and mentally, he reflected deeply on what he wanted next. “I lost a little bit of a step last year,” Lopez admitted, “but I’ve always hung my hat on defense.” Now, in a more defined role off the Cubs bench, he’s rebounded and found his footing at third base. What matters to him most now is being part of a winning team—and he believes he’s found that with the Cubs.
Brad Keller, meanwhile, has quietly become a bullpen asset. Just last year, he spent a brief stint with the Sox, then bounced to Boston before settling in Chicago again—this time on the North Side. He’s one of just 209 players to have suited up for both Chicago clubs, and he doesn’t take that lightly. “It’s special,” Keller said. “And the culture here? It’s built for winning. Everyone’s locked in.”
The emotional undercurrent of this series is real. These aren’t just three players switching teams—they’re switching sides in a rivalry that means everything to this city. They’ve lived both locker rooms, experienced the highs and lows, and now, they’re wearing a different shade of blue with one goal in mind: win.
So as the Cubs and Sox square off at Wrigley Field, this series is more than just about bragging rights. It’s about redemption, opportunity, and embracing a new chapter. For Flexen, Lopez, and Keller, it’s a chance to thrive where the energy matches their hunger.
This weekend, the South Side memories fade into the past. It’s all about the present—and the North Side future.
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