Chicago Cubs: Bryse Wilson signs with hated division rival after electing free agency

Earlier this year, the Chicago Cubs signed right-handed relief pitcher Bryse Wilson in hopes that he could help bring some stability to their injury-riddled bullpen. After all, he had previously pitched for Cubs manager Craig Counsell during his days with the Milwaukee Brewers, and the familiarity helped make sense of the deal despite Wilson’s struggles in 2025 and 2026.

Unfortunately, it did not work out. Wilson appeared in just two games for Chicago and had an 8.22 ERA. The Cubs decided to designate him for assignment after they picked up Jake Woodford. After clearing waivers, he elected free agency. Now, he has rejoined Chicago’s biggest rival.

Former Chicago Cubs RHP Bryse Wilson signed with the Milwaukee Brewers

On Friday morning, it was reported by MLB insider Robert Murray that Wilson has agreed to a contract with the Brewers. What is not clear, though, is whether it is a Major League or minor league contract. If it is a Major League deal, Milwaukee will have to clear a spot for him on their 40-man roster.

Ironically, Woodford, whom Chicago signed before designating Wilson for assignment, was previously DFA’d by Milwaukee before signing with the Cubs.

This will be Wilson’s second stint with the Brewers organization. He pitched in Milwaukee from 2023-2024 and appeared in 87 games with a 3.42 ERA. His best season was in 2023 (Counsell’s final year there) when he appeared in 53 games, went 6-0, and posted a 2.58 ERA.

After leaving Milwaukee, Wilson had stints with the Chicago White Sox, Philadelphia Phillies, and Cubs. In that time, he was 0-2 with a 6.63 ERA. Clearly, it appears his hope is that he will be able to regain his form back with the Brewers organization.

The move makes sense for Milwaukee, who, like the Cubs, are starting to deal with some injuries to their pitching staff. This past week, two-time All-Star Brandon Woodruff was placed on the injured list for the second time this season. An MRI revealed a new injury to his surgically repaired shoulder, and the next steps for him are not clear that this point.

Wilson almost certainly will not be used as a starter in Milwaukee, if he even is added to the Major League roster at some point. However, he could give them another long relief option if they move someone like Chad Patrick back to the rotation.

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