For a trio of Cubs, the City Series represents the other side of the rivalry with the White Sox

Chicago Tribune

16-05-2025

Chris Flexen always enjoyed pitching at Wrigley Field throughout his career, but his start at the historic ballpark took on a different level of intensity last year when took the mound for the White Sox.
Flexen remembers it as the Sox's most intense series of the season, one that went down in modern Major League Baseball history with the most losses. Now on the division-leading Cubs (25-19), Flexen — with infielder Nicky Lopez and right-hander Brad Keller going from representing the South Side in 2024 to the North Side this year — is looking forward to experiencing the rivalry from the other side. He started a game in each series last season, holding the Cubs to one run and six hits in nine innings, though the Sox lost both games.
'The biggest thing is you just see the city of Chicago come out and support their teams, no matter what side it's on, the blue might be a little stronger in the stands,' Flexen said. 'It was a lot of fun. It's definitely a cool, awesome city rivalry to be a part of and it's fun to see the fans come out and really get into the games.'
He didn't anticipate any friendly trash talking with his former Sox teammates leading up to this weekend's City Series.
'I'm not much of a trash talker,' Flexen said, chuckling. 'More of a check in to see how you're doing.'
Flexen led the Sox with 160 innings while appearing in 33 games (30 starts). He didn't experience the level of personal or team success he envisioned going into the year, posting a 4.95 ERA en route to the Sox's record 121 losses. The Sox (14-30) enter this weekend with the worst record in the American League and have the same record as the 2024 squad through 44 games.
Flexen tried to not dwell on the struggles within the moment last year, instead focusing to make sure he was prepared every day to go out and compete.
'That's something that got me through that year and we had good guys over there, good teammates so you still pull for one another,' Flexen said. 'But as an individual, something that you can control is being ready every day. I try to take pride in that and at the end of the end of the day, whether high or low, going good or going bad, you can show up and compete. And not that it's something I've learned, but it definitely was the test and I definitely put my best foot forward.'
When the Cubs had Lopez in big-league camp this spring, they believed the 30-year-old Naperville native was better defensively than his career-worst metrics from last year indicated.
'I think I lost a little bit of a step last year,' Lopez said. 'I'm not trying to make excuses, but given the circumstances, it was a pretty tough year for a lot of us over there. And so this offseason, when we were talking to teams, a lot of it was some of the numbers defensively took a hit that in the first five years of my big-league career, that never was the case. I've always hung my hat on on defense.'
Lopez, who was fourth on the Sox in plate appearances in 2024, has seen limited action in his bench role but he understood that was the situation when he agreed to a major-league deal with the Cubs last month. Both sides felt the fit was right dating to the initial minor-league contract he signed as he spent the spring trying to make the roster. His defense has gotten back on track at third base, where he has started nine games for the Cubs.
Reflecting on 2024 with the Sox, his lone season with the organization following an offseason 2023 trade from the Atlanta Braves as part of the package for reliever Aaron Bummer, Lopez noted how well the Sox clubhouse stuck together, though 'you had to kind of dig deep and know that this is tough, we were going to get our butts kicked every single day and it was just one of those things.'
So when Lopez evaluated his offseason options, he reflected on the struggles and what he wanted in the big picture for his career. Of course every player wants to stick for 10 years in the majors and be an everyday player, but if the latter wasn't going to happen, Lopez knew he playing for a winner was a must.
'When we started talking to the Cubs, I was like, man, this is a great fit, I want to come here and do anything I can to help this team win,' Lopez said. 'And so it was definitely a reflection period, how can I stick? Where can I go to stick? And this is a perfect fit.'
Right-hander Brad Keller has been a bright spot in the Cubs bullpen this year after spending three weeks with the White Sox from late April until mid May before becoming a free agent and going to the Red Sox for the rest of the season. Keller said it's special to get to play for both Chicago teams — he's one of 209 players to have done so, according to Cubs team historian Ed Hartig — and praised the Cubs for the environment that has been created.
The trio of former Sox knew when they joined the organization that reaching the postseason has been a priority from the onset. That brings performance-related expectations, which each player has embraced, with big-picture team goals that create a very different feeling from what they experienced with the rebuilding Sox.
'It's just been a heightened level of focus here, and it's just been a lot of fun,' Keller said. 'We're a really good team and we're built for sustained success.'