Chicago Cubs could swipe Brewers 2x All-Star to replace Shota Imanaga

The Chicago Cubs are coming off of a season that saw them go a respectable 92-70, but fall to the team with Major League Baseball’s best record, the Milwaukee Brewers, in the National League Division Series. There were, of course, several reasons why the Cubs could not overtake the Brewers in the NLDS, and the lack of quality of depth of their starting pitching was no small contributor.

This is why it was surprising that, on Monday morning, it was reported that Chicago had declined their option on left-handed pitcher Shota Imanaga, and 2024 All-Star who was 9-8 with a 3.73 ERA last season.

Had the Cubs picked up Imanaga’s option, they would have been on the hook for three years and $57 million, or $19 million a season.

The Chicago Cubs could steal Brandon Woodruff from the Milwaukee Brewers

Of course, the Cubs still could bring Imanaga on a qualifying offer or a more affordable deal. That being said, the starting pitching market is lucrative and the 2024 All-Star could garner a rich contract elsewhere.

Over the past few seasons, Chicago’s ownership has taken a cost-saving approach to free agency and player retention, causing many fan-favorites to find themselves playing elsewhere.

But one option at starting pitcher that could replace Imanaga could come from the aforementioned Brewers, who just saw their two-time All-Star starer Brandon Woodruff decline his part of the mutual option he had with the team:

#Brewers SP Brandon Woodruff has declined his half of his mutual option, per @AdamMcCalvy

Woodruff, 32, is a free-agent. pic.twitter.com/wHVp23ffPi

— MLB Deadline News (@MLBDeadlineNews) November 3, 2025

Woodruff was 7-2 with a 3.20 ERA in 12 starts last season, his first after missing nearly two full years due to a should injury.

The two-time All-Star did not pitch for Milwaukee in the postseason, and his injury history likely means he will not be very expensive. In fact, Jim Bowden of The Athletic predicts he will get a two-year $22 million contract in free agency, or $11 million.

Obviously, manager Craig Counsell is very familiar with Woodruff, whom he managed during his days in Milwaukee. There is a risk, of course, given Woodruff’s injury history. That being said, when healthy, he is one of the best pitchers in the National League.

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