Cubs Would Land Rival's Former Starter in 'A Poetic Twist'

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Chicago White Sox pitcher Aaron Civale

Could the Milwaukee Brewers ’ quick trigger to remove a potential distraction wind up providing their biggest rival with a needed piece for a playoff run?

Right-hander Aaron Civale was recently involved in a midseason trade for the third straight year. Milwaukee, who had acquired Civale from Tampa Bay on July 3, 2024, dealt him to the Chicago White Sox on Friday after Civale balked at a move into the Brewers’ bullpen. But according to MLB insider Bob Nightengale of USA Today, Civale’s tenure with the White Sox will likely be short-lived.

“They plan to trade him at the July 31 deadline, believing they could get at least a couple of mid-tier prospects in return,” Nightengale wrote in the “Around the Basepaths” section of his Sunday column.

Wouldn’t it be interesting if all this wheeling and dealing ended up putting Civale in Wrigleyville? Matthew Postins of Cubs on SI believes that could happen , citing a need for starting pitchers and a roster of prospects to suggest that Civale, a free agent at the end of this season, would be a good fit for the Chicago Cubs .

Milwaukee Granted Aaron Civale’s Request With Trade to White Sox

When Milwaukee announced the promotion of Jacob Misiorowski to make his Major League debut on Thursday, the team also indicated Civale would be moved out of the starting rotation to make room for the team’s top prospect. Civale, who has not pitched as a reliever in a regular season game since he was in college at Northeastern, expressed his dissatisfaction with that decision, requesting instead that he be traded to another team that valued him as a starter.

“We’re exploring the options to give me the chance to do what I do best, and that’s to go out there and start,” the 30-year-old Civale said Thursday.

“Aaron is not angry or banging his fist on the table,” Civale’s agent Jack Toffey said to Ken Rosenthal of The Athletic. “But it’s a little confusing because he did not pitch his way out of the rotation whatsoever. It’s more of a subjective choice the organization is making.”

It took under 24 hours for a trade to be made.

After acquiring Civale less than 12 months ago for a promising infielder in Gregory Barrios, who is currently the No. 17 ranked prospect in Tampa Bay’s system, Milwaukee flipped the pitcher, who had a 40-37 career record and a 4.06 ERA, for 27-year-old first baseman Andrew Vaughn . It certainly felt like a rushed, sell-low move, and the Brewers immediately sent Vaughn – a career .248 hitter who has struggled this season, slashing .189/.218/.314 – to Triple-A Nashville.

Civale, who spent about seven weeks on the injured list with a strained hamstring at the beginning of the season, made his debut for the White Sox on Sunday. Civale gave up six hits and two runs over five innings, walking four and striking out four, as Chicago lost 2-1.

“Not the cleanest,” Civale said. “It’s been a whirlwind of a week.”

Aaron Civale Moves to His Fourth Team in Two Years

Actually, it’s been a whirlwind of a few years for Civale. A third-round pick by Cleveland in the 2016 draft, Civale debuted with the then-Indians in 2019. Civale made 99 starts over four-plus seasons with Cleveland, who traded him to Tampa Bay in a deadline deal on July 31, 2023 for first base prospect Kyle Manzardo.

Less than a year later, Civale was sent to Milwaukee. Less than a year after that, he was on to the White Sox.

“It never gets easier,” Civale said. “There’s comfort in experience that you have, but every time it’s new and it’s a different challenge in itself. You’re trying to make that adjustment as quick as you can.”

Another adjustment could be just a few weeks away.

While the Cubs have built a 5.5-game lead in the NL Central, their 2025 campaign has been marred by inconsistency and injuries among the starting rotation. Civale would provide them with a valuable mid-rotation innings-eater who will likely cost little more than a prospect such as Jack Neely or Christian Franklin.

And in what Tyler Koerth of ChiCity Sports called “a poetic twist,” the move would allow the Cubs to throw a little bit of shade Milwaukee’s way.

“The North Siders would be landing a starting pitcher from a division rival, who paid a premium for just a year ago, now at a likely discount,” Koerth wrote. “It would not only bolster Chicago’s rotation for the stretch run but also serve as a subtle dig at the Brewers’ misfire.”

Dave Benson Dave Benson is a longtime writer with over three decades of experience in a variety of mediums, including 15 years covering high school, collegiate and minor league sports in the St. Louis metropolitan area. Dave is also a licensed English teacher and spent a few years teaching at the middle school level. More about Dave Benson