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As the Chicago Cubs prepare for a playoff run, there are some key offseason decisions that loom for the front office. Kyle Tucker's free agency has been one of the main storylines of the Cubs' season, but the Cubs also have a decision to make when it comes to Shota Imanaga's contract. Certainly, the playoffs this season are the priority for the front office, but they likely have begun to map out some of their offseason decisions.
Along those lines, there are several expected free agents the Cubs have on their roster who have performed well this offseason, but the team likely won't be in a rush to re-sign them.
Drew Pomeranz, LHP
Pomeranz has been one of the hidden gems of the Cubs' bullpen this season, entering the weekend with an ERA of 2.34 in 49 appearances. That said, there is some volatility when it comes to relief pitchers, and Pomeranz seems like a prime candidate for regression in 2026 with an xERA of 3.81 and FIP of 3.47.
Reese McGuire, C
McGuire has done an admirable job serving as the backup catcher to Carson Kelly, as Miguel Amaya's 2025 season has been plagued by injuries. With a healthy Amaya in the fold for 2026 and Moises Ballesteros needing to be with the Major League team, the Cubs likely won't place much of a priority on bringing McGuire back this offseason.
Kyle Tucker, OF
There's some surprise that we have reached this point with the Cubs and Tucker. Despite the injuries and slump that have plagued Tucker's second half, he remains among the best National League outfielders in terms of wRC+. That said, adding in the injuries that made the ending of his final season in Houston awkward, the Cubs might be best using their money elsewhere and handing right field over to Owen Caissie.
Colin Rea, RHP
There is some cheating with this one, as the Cubs technically do have control over Rea for the 2026 season, holding a $6MM club option. Rea has been a savior for a Cubs' pitching staff that has dealt with injuries since the start of the season, but it feels like the Cubs will be willing to let the veteran go this offseason.