The Cubs have bigger things on their mind right now than winter shopping lists. With the pennant race still in front of them, and the memories of the 2019 and 2023 September collapses hanging around, Chicago has no reason to get cozy until October is officially secured.
But the front office is already looking ahead. Jed Hoyer and his staff have plenty to sort through once the season ends, and a good chunk of the roster is heading toward free agency.
Some players are obvious candidates for new deals. Others, even after making real contributions, probably fit better in the “thank you and good luck” category.
Matthew Boyd is the first name that fits that mold. The left-hander signed a two-year deal with the Cubs in December 2024 and immediately gave them exactly what they hoped for, then some.
He put together a 3.21 ERA over 31 starts last year, his first healthy season since 2019, and has followed that with a solid 4.05 ERA in 18 outings this season. That’s a strong run overall, and no one should pretend otherwise.
Still, the warning signs are there. Boyd is 35, and for the second straight year his season has started to wobble late.
Since the calendar turned to August this year, he has a 5.20 ERA and 6.42 FIP in six starts. Last year, he finished with a 5.16 ERA from July 28 on.
That kind of late-season fade is hard enough to live with once. At his age, it becomes a bigger concern.
The Cubs may be better off letting another team deal with what comes next.
Carson Kelly has been just as valuable in a different way, and maybe even more surprising. Signed in December 2024, he has given the Cubs stability behind the plate that they had been searching for since Willson Contreras left in free agency.
Over the last two years, Kelly has hit .255/.338/.412 in 214 games, which is 12% better than league average. For a catcher, that stands out even more.
He’s backed it up with solid defense, which is why he’s become the kind of player a team can plug in and trust. The problem for Chicago is that those kinds of catchers don’t come cheap.
Kelly should draw strong interest in free agency because there just aren’t many reliable options at the position. Add in Owen Ayers, the catching prospect some have wanted to see in the majors this year, and a reunion for the 2027 season looks unlikely.
Then there’s Tyrone Taylor, who has made the most of a role that was never supposed to look this important. He arrived in the trade that sent Clay Holmes to Chicago, and while Holmes has become the Cubs’ ace and a player they should make every effort to keep, Taylor has outperformed expectations in his own lane. Since joining the team, he has hit .412/.462/.565.
That kind of production from a part-time player has to be viewed carefully, of course, but Taylor’s 133 wRC+ this season still marks him as an elite bench piece. Plenty of teams will notice that in free agency.
The Cubs, though, may not have room to promise him much more than what he already has. Matt Shaw is already set as a lefty-mashing outfielder next year, and if Chicago wants a veteran out there, lefty Michael Conforto is the better fit.
Taylor has done the job. It just may not lead to a second act in Chicago.
In Other News...
Cubs Fans Have Another Reason To Revisit The Kyle Tucker Trade
Hayden Wesneski has given Cubs fans one more reason to keep looking back at the Kyle Tucker deal, and not just because Tucker never spent long in Chicago. The right-hander, included in the trade package sent to Houston, has looked much more like a dependable starter after working his way back from Tommy John surgery, and his early run with the Astros has been enough to make the return package feel more complicated than it did at the time.
Through his first seven starts this season, Wesneski has paired a 3.18 ERA with a much cleaner home-run profile than he showed with the Cubs. For Chicago, that only adds to the familiar debate over whether the price for Tucker was too steep for a player who ended up contributing mostly in one season, especially if one of the pieces going the other way is beginning to settle in elsewhere. [Read more 🡒]
Cubs Face One Offseason Decision That Could Reshape Their Rotation
The Cubs already have a handful of offseason decisions sitting in front of them, with mutual, club and player options spread across the roster for the 2027 season. In most cases, the outcome feels familiar enough: mutual options rarely get exercised, and the front office may choose to keep some players while moving on from others as it trims the roster around the edges and preserves flexibility for the winter ahead.
The bigger question is Clay Holmes, whose player option is expected to go unpicked, putting him on track to test free agency. For a Cubs rotation that could look different depending on how those other options resolve, that makes Holmes a name worth watching closely. If he reaches the market, Chicago could have a real chance to make him a priority, but the timing also leaves the club with one more important decision in a market that may already be shifting beneath it. [Read more 🡒]
Cubs Seem Ready To Reverse A Javier Assad Decision
Javier Assad is back with the Cubs and eligible to be recalled from Triple-A Iowa ahead of the weekend series against the Marlins, a sign the club may be ready to revisit a pitching decision it made earlier in the year. Chicago still has not announced its starters for Saturday or Sunday, and Assads presence around the team puts him squarely in the mix if the Cubs decide they need another arm to bridge the stretch in front of them.
Jacob Webb and Tyler Ferguson are also part of the roster conversation as the Cubs sort through possible pitcher moves, though nothing has been made official. For a team trying to line up its rotation with a series in Miami, the timing matters, and Assads availability gives Chicago another option while it weighs how to reshape the staff for the weekend. [Read more 🡒]