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The Chicago Cubs avoided being swept by the Milwaukee Brewers in the NLDS and even managed to restore hope toward the tail-end of the series. However, with the Brewers advancing to the NLCS and the Cubs beginning their offseason, the point remains that there is a large gap between where the Cubs are and the top of the National League Central division.
The decisions that Craig Counsell made during the Cubs' playoff run were polarizing, but they may be more indicative of the roster he was provided. Last offseason, it seemed that Counsell's voice was an important factor in the team's free-agent decisions, and it would seem that will be the case moving forward.
Former Craig Counsell players the Cubs must target this offseason
Brandon Woodruff, SP
A lat injury led to the Cubs avoiding Brandon Woodruff during the NLCS, and the 32-year-old has a mutual option for 2026. It feels like Woodruff will hit free agency, and he feels like the sequel to the Cubs' signing of Matthew Boyd last offseason. Returning from a shoulder surgery that wiped out his entire 2024 season, Woodruff posted a 3.20 ERA in 12 starts with the Brewers in 2025 while striking out over 32% of the hitters he faced. The ability to miss bats is something that the Cubs' pitching staff has lacked, and Woodruff would be a direct answer to that need.
Devin Williams, RHP
After being traded from the Milwaukee Brewers to the New York Yankees last offseason, it was a disastrous 2025 season for Devin Williams in New York. Williams posted an ERA of 4.79 in 67 appearances. Williams' struggles led to the Yankees overhauling their bullpen at the deadline, and it would seem that Craig Counsell's bullpen ace will have a new home in 2026. That home should be with the Cubs.
Hoby Milner, LHP
Drew Pomeranz, Caleb Thielbar, and Taylor Rogers all will be free agents after the season, leaving the Cubs with no left-handed options in their bullpen. Hoby Milner could be someone the Cubs target this offseason. Milner was once Counsell's left-handed specialist with the Brewers, and posted a 3.84 ERA in 73 appearances with the Texas Rangers last season.