3 big reasons why Brandon Woodruff should fit into the Cubs’ offseason plans

Starting pitching has been the Chicago Cubs’ biggest need all season. This offseason presents a prime opportunity to bolster that rotation, and Brandon Woodruff, currently with the Milwaukee Brewers and a longtime player under Craig Counsell, should definitely be on their radar.

Three reasons why Brandon Woodruff should fit into the Chicago Cubs offseason plans

Jon Heyman was the first to put the connection together that the Cubs and Woodruff could benefit from uniting this off-season. Chicago probably won’t be involved with top free agent pitchers like Framber Valdez or Dylan Cease, but the stars could align to land Woodruff. Here are three reasons why.

The Cubs need starting pitching

This season has been a clear reminder for the Cubs that starting pitching depth is essential. Despite having Shota Imanaga, a healthy Justin Steele, Matthew Boyd, Javier Assad, Cade Horton, and Ben Brown all expected back in 2026, injuries have repeatedly stretched Craig Counsell’s rotation thin. The old adage, “you can never have enough pitching,” is one Chicago would be wise to live by this offseason.

Reunion with Craig Counsell

Woodruff was drafted by the Brewers in 2014 and debuted under Counsell in 2017. The two were together for several years, until Counsell left, and Woodruff, despite coming off a major shoulder surgery in 2023, has had a triumphant return to the mound this year. He has a 3.32 ERA this year and a career 3.11 ERA. Woodruff’s fastball isn’t what it used to be, but he’s become more of a pitcher rather than relying on straight heat to get batters out.

Chicago can offer Woodruff more money than the Milwaukee Brewers

The Brewers made a commendable move by Brandon Woodruff to a two-year, $17.5 million deal while he rehabbed from shoulder surgery. That contract includes a $20 million mutual option for 2026, a figure that one side is likely to decline. If Woodruff hits free agency, the Cubs could be in a prime position to outbid Milwaukee, a team historically hesitant to commit big money to pitchers. A contract perhaps slightly north of Matthew Boyd’s recent deal, two years, $29 million with a club option for a third, could be enough to land him.

If Woodruff hits the open market, as expected, the Cubs should be among the first in line. With a clear need for dependable starting pitching, deep familiarity between Woodruff and Counsell, and the financial flexibility to make a competitive offer, the fit makes too much sense to ignore.

It would be a bold move, poaching a franchise cornerstone from a division rival, but one that could help solidify Chicago’s rotation as they look to continue to be competitive.