The Chicago Cubs came one game short of reaching the NLCS after returning to the MLB playoffs for the first time since 2020. Chicago forced a Game 5 of the NLDS against the division rival Milwaukee Brewers but ultimately fell short as their season came to an end. The Cubs will enter the offseason looking to retool for 2026 in hopes of returning to the postseason once again and making an even deeper run.
The Cubs’ pitching depth was especially thinned in the postseason, with a lack of quality arms leading to the team’s early exit. Chicago will likely need to add a few additional quality pitchers to eat up innings on the roster.
However, one of those arms will not be Keegan Thompson. The Cubs’ third-round pick in the 2017 MLB Draft elected free agency on Tuesday, according to the MiLB Transaction Log. While Thompson did not appear on the roster for the NLDS, he has been a quality arm for the Cubs and could have made an impact in 2026 despite being on Triple-A to finish off the year. Over the last four years, the 30-year-old right-hander has pitched in 104 games. Thompson has owned a 17–11 record, 225 strikeouts in 227 1/3 innings and 1.324 WHIP. Thompson operated as a starter in 2021-22 before transitioning to a relief role. He will likely look to compete for a spot on a major-league roster in 2026.
Thompson spent most of 2025 with Triple-A, where he posted solid numbers and remained a reliable option for spot starts and long relief. Though he didn’t crack the postseason roster, his versatility and experience made him a candidate to contribute next season, especially with the Cubs facing turnover on the mound. His decision to test free agency highlights the shifting dynamics of Chicago’s pitching staff, as the front office evaluates internal depth and explores external options.
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