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Chicago Cubs facing major Matthew Boyd dilemma

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Chicago Cubs facing major Matthew Boyd dilemma

Originally posted on ChiCitySports | By Paul Magno | Last updated Sep 6, 2026 1:26 PM ET

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The Chicago Cubs will have some major decisions to make this coming offseason. A good portion of the team will be eligible for free agency at the end of this season.

At the completion of the 2026 season, the Cubs will see the following players from the current roster become free agents: Matthew Boyd, Shota Imanaga, David Peterson, Kevin Gausman, Carson Kelly, Ian Happ, Seiya Suzuki, Michael Conforto, Tyrone Taylor, Ryan Rolison, Trent Thornton, Aaron Civale, Caleb Thielbar, and Hunter Harvey. Clay Holmes, meanwhile, has a $12 million player option for 2027 that he’s expected to turn down in favor of free agency.

That’s about half the team possibly moving on. It’s probably not feasible to add so many new names and simultaneously expect to compete for a championship.

So, obviously, the Cubs may like to keep at least some of their potentially outbound players. They’ve already worked on some of that by extending Nico Hoerner earlier in the season and by letting Jameson Taillon and Hoby Milner go. But there’s a lot more work to be done in that regard.

Some of the decisions are easy. They should try to hold on to Clay Holmes and at least one of their corner outfielders. Tyrone Taylor may also be a smart budget-minded keep.

Making a decision on Matthew Boyd

Apr 27, 2026; San Diego, California, USA; Chicago Cubs starting pitcher Matthew Boyd (16) delivers during the first inning against the San Diego Padres at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images

One of the more difficult decisions will be regarding Matthew Boyd.

The 35-year-old lefty came to the Cubs prior to the 2025 season on a budget-friendly two-year, $29 million contract after working his way back from elbow surgery. He exceeded all expectations in his first year with the Cubs, pitching his first full season since 2019 and finishing the year with a 14-8 record and a 3.21 ERA.

This season hasn’t been great. Two IL stints have limited his innings and he’s had some consistency issues when healthy. But his 4.05 ERA is solid enough and his average of 5.2 innings per start is decent.

Doubts and questions

Apr 1, 2026; Chicago, Illinois, USA; Chicago Cubs pitcher Matthew Boyd (16) delivers during the first inning against the Los Angeles Angels at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images

The problem is that there is legitimate doubt as to just how much more juice Boyd has in his arm, especially after a second straight season where he appears to be fading late in the year. Chicago will have a real need for an anchor in their rotation with the loss of so many starting pitchers and the insecurity surrounding those who remain on the roster. Boyd is probably not that guy at this point in his career.

Nick Deeds of Cubbies Crib sums up the Cubs’ dilemma in approaching the re-signing of Boyd:

“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.”

Maybe if the Cubs could get him on another short-term deal at a similar price, a re-signing would be advisable. A nice one-year contract giving him a decent raise for 2027 could be a smart move for the team. But Boyd is probably going to be looking for more money in a longer deal.

At 35 years of age, with the mileage he has on his body, the Cubs would be smart to move on if they can’t get another budget deal from him.

This article first appeared on ChiCitySports and was syndicated with permission.

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