For right now, all eyes among Chicago Cubs fans remain squarely focused on the pennant race. There's still plenty of work to do before the team punches their ticket to October, and the September collapses of 2019 and 2023 should keep the club from getting too comfortable until their spot in the postseason is completely locked in.
The same is not true, however, for the front office. President of baseball operations Jed Hoyer and his team are surely already hard at work preparing for the upcoming offseason, which will see a significant portion of this team reach free agency. There's been plenty of talk of late about which players the Cubs need to make every effort to re-sign this winter, but who are they better off letting walk? A look at some of those players:
Matthew Boyd has been an asset for the Cubs, but cracks are starting to form
It would be unfair to Matthew Boyd for fans to judge him solely on his recent performance. After signing a two-year deal with the Cubs in December 2024, Boyd was a revelation for them last year with a 3.21 ERA across 31 starts in his first healthy season since 2019. That alone was impressive, and this year Boyd has followed it up with a decent performance across 18 outings, good for a 4.05 ERA overall.
While the deal to bring him into the fold was undeniably a good one, it wouldn't make sense to bring him back next year. Boyd is already 35 years old, and for the second year in a row he's wearing down late in the season. This year, Boyd has a 5.20 ERA and 6.42 FIP in six starts since the calendar flipped to August. Last year, he posted a 5.16 ERA from July 28 onwards. Those late-season slumps are likely to only get worse as Boyd gets older, and the Cubs ought to let that be another club's problem.
Carson Kelly's exceptional tenure likely prices him out of a Cubs reunion
Another player signed in December 2024 who has exceeded every reasonable expectation, Carson Kelly has solidified the Cubs from behind the plate in a way that they had been struggling to find ever since Chicago let Willson Contreras walk in free agency. Over the last two years, Kelly has hit .255/.338/.412 in 214 games. That's 12% better than the league average hitter, which is even more impressive when you consider that the average catcher is a subpar hitter.
Kelly's paired that strong offense with solid defense, making it easy to set him and forget him behind the plate. Losing him will sting for the Cubs, to be sure, but the reality is that Kelly is likely to enjoy a strong market in free agency thanks to the dearth of solid catching options around the game right now. Combine that with up-and-coming catching prospect Owen Ayers, who some have clamored to see called up to the majors this year, and it's hard to see Kelly returning for the 2027 season.
Tyrone Taylor has done everything asked of him... but he's still just a hired gun
While Clay Holmes has established himself as the Cubs' ace and someone the team should do everything they can to retain next year, nobody expected the second player in that trade to be nearly as impressive. Tyrone Taylor has defied those expectations, however, and is slashing an absurd .412/.462/.565 since joining the team.
Obviously, a month of production from a part-time player needs to be taken with a grain of salt, but Taylor's 133 wRC+ on the season makes him an elite bench piece. That should be attractive to plenty of teams in free agency but, given that he's on a Cubs team where he can't even find reliable starts, it's safe to say he'll be playing elsewhere in 2027. Matt Shaw is already locked in for a lefty-mashing outfielder next year, so lefty Michael Conforto is a better choice if the Cubs want to keep a veteran.
