Chicago Cubs predicted to re-sign these outgoing free agents for 2027 run

The Chicago Cubs will have a big dilemma on their hands as they head into the 2027 season. They’ll also have the unique opportunity to re-make the roster, eliminating many of the past mistakes, over the course of this one offseason.

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At the official end of this baseball year, the Cubs could see a mass exodus of veteran talent leave via free agency. They could lose their entire end-of-season starting rotation (Matthew Boyd, Shota Imanaga, Kevin Gausman, Clay Holmes, David Peterson). They could also lose relievers Hunter Harvey, Aaron Civale, and Trent Thornton—with Colin Rea and Jacob Webb staring down club options for 2027. On the position player side of things, outfielders Ian Happ, Seiya Suzuki, Michael Conforto, and Tyrone Taylor, as well as catcher Carson Kelly, could also be lost via free agency.

The reality, though, is that it’s just not practical or feasible to let everyone walk. Some of the outgoing Cubs will have to be brought back, just for the sake of economics and logistics.

Predictions on who will be back

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Jake Misener of Cubbies Crib recently offered his thoughts on who Chicago will re-sign and why.

Per Misener:

Ian Happ

“A career-low batting average driven almost entirely by his struggles from the right-handed side of the plate (.148/.221/.273) has forced him into platoon duties in the second half…I think a soft market could lead to a team-friendly reunion this offseason.”

David Peterson

“Picked up out of sheer desperation in June, David Peterson helped keep the Cubs’ rotation afloat as it battled injuries and ineffectiveness…the left-hander fits perfectly with how the team is constructed.”

Clay Holmes

“The starting pitching market is light behind Tarik Skubal, so re-signing Clay Holmes will be a tough task for the Cubs’ front office…Holmes will decline his $12M player option, but Chicago brings him back on a multi-year deal to anchor the rotation.”

Jacob Webb

“Big-picture, Jacob Webb has been good far more than bad this year. The Cubs will pick up his $2.5 million option for 2027.”

The reasonable returns

And all of this certainly makes sense.

Happ wants to stay in Chicago and may have a tough time finding a deal better than what the Cubs might offer him, especially after becoming, essentially, a platoon player in 2026.

Holmes, with his extreme groundball stuff, is the perfect Cubs fit, even though he struggled down the stretch. Peterson, meanwhile, would be a good budget pickup to slide into the fourth or fifth slot of a rotation that will need some miracle work over the offseason.

And, yeah, $2.5 million for Webb is reasonable and workable as someone who will—hopefully—go back to lower-leverage middle relief in support to a beefed-up back-of-bullpen.

Best of all, the re-signings above would still leave ample room for some impact free agent signings to round out the offseason.

This winter should be an interesting one.

The post Chicago Cubs predicted to re-sign these outgoing free agents for 2027 run appeared first on ChiCitySports.

Source: https://www.chicitysports.com/chicago-cubs-free-agents-returning-2027-holmes-happ-peterson-webb/