Milwaukee's biggest rival continues to add former Brewers to their late-season roster

What do Aaron Civale, Drew Pomeranz, Collin Rea, Taylor Rogers, and now Joe Ross all have in common? They are all pitchers who were once members of the Milwaukee Brewers and are now part of the Chicago Cubs' organization.

Civale is the most recent member of the Brewers, who, earlier this year, demanded a trade after it was announced that he was no longer a starter on the team. Civale was dealt to the Chicago White Sox for Andruw Vaughn, then subsequently placed on waivers by the South Siders, and claimed by the Cubs.

Rea and Ross were Brewers in 2024, with Rea having ties to Cubs manager Craig Counsell as they were together in 2023. Ross, on the other hand, doesn't have ties to Counsell, as his lone season with the Crew came in 2024 after Pat Murphy had already taken over as skipper. Ross had a resurgent year with Milwaukee last year, inked a one-year deal with Philadelphia, but was released after posting a 5.12 ERA. The Cubs scooped him up and signed him to a minor league deal.

Taylor Rogers, the left-handed reliever Milwaukee originally acquired in the 2022 Josh Hader trade, landed in Chicago this season after the Reds opted for a rare intra-division deal. Meanwhile, Drew Pomeranz, who had a strong stint with the Brewers in 2019, is now back in the majors and finding success under Counsell once again, following a four-year absence from MLB action.

Taking it a step further, former Brewers first baseman Carlos Santana, who played in Milwaukee in 2023, recently signed with the Cubs after being released by the Guardians. His decision to join Chicago came after a personal phone call from Counsell, and now, Santana is poised for yet another round of October baseball.

Not all of these former Milwaukee Brewers now on the Chicago Cubs are postseason eligible

Of this group of former Brewers now with the Cubs, Ross is the only one currently on a minor league deal. His release from the Phillies in late August came at a critical time, as players must be in an organization by September 1 to be eligible for the postseason. According to Ross’s transaction log, he did not meet that deadline.

With the Brewers and Cubs out of regular season matchups, the next time Milwaukee may see any of their former players now wearing a Chicago uniform would be in October. Whether it’s Santana’s veteran bat, Rogers’ late-inning lefty arm, Pomeranz’s comeback story, or Civale now accepting a role in the pen that he refused to take with the Brewers, each storyline adds fuel to a potential postseason showdown.

Combine that with the added drama of Counsell and now-third-base coach Quinton Berry leaving the Brewers for their division rival, and a playoff series between these two closely linked cities could be one of the most intense and emotionally charged matchups of the October slate.