The Chicago Cubs, in a lot of ways, are facing somewhat of a “win now” situation in 2026. Looking up and down the roster, one realizes just how much of the team’s core talent could be leaving after the coming season.
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Literally, half the 26-man roster could be departing Chicago after the 2026 campaign:
Ian Happ
Seiya Suzuki
Nico Hoerner
Matthew Boyd
Jameson Taillon
Shota Imanaga
Carson Kelly
Colin Rea
Caleb Thielbar
Hoby Milner
Jacon Webb
Hunter Harvey
Tyler Austin
Now, to paint a clearer picture, it should be noted that the Cubs hold club options on Rea and Webb for 2027 and that a mutual option is on the books for Boyd, Kelly, Thielbar, and Harvey (although, seriously, could Boyd be expected to take his one-year $15 million option for 2027 if he has another great season in 2026?).
Still, there’s no arguing that there will be major turnover in 2027 and that big decisions will have to be made, especially regarding the most senior veterans on the above list– Happ, Suzuki, Hoerner, Taillon, and Imanaga.
Will the Cubs opt to extend any of the above? Who will they let drift away into free agency, with everyone knowing full well that, realistically, the team won’t get into a bidding war for any of them once they’re on the open market?
Here’s a look at who the Cubs could likely extend and who will be saying goodbye to Chicago after next year.
Extending Nico Hoerner should be a no-brainer
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Nico Hoerner is the best Cubs second baseman since Ryne Sandberg. Period.
Aside from becoming one of baseball’s most consistent contact hitters over the last few seasons and establishing himself as a two-time Gold Glove winner, he’s also become a valuable team leader with the Cubs. Last season, as the offense slumped en masse, he practically carried the team through the latter part of the season and through the playoffs.
CBS Sports’ Mike Axisa estimates that a Hoerner extension might be had for about $120 million over 6 years. That’s a reasonable price for what the soon-to-be 29-year-old brings to the table, given his ability and his importance to the team. He’s already shown himself willing to sign a contract extension, going for a 3-year, $35 million deal prior to the 2024 season, so he could be open to another offer, with a fair and reasonable raise attached.
The Cubs front office should be tarred and feathered if they don’t try to make this happen.
Ian Happ might “steady” his way into a new deal
Left fielder Ian Happ is not the flashiest of talents or the most obvious of stars, but the Cubs’ decision on extending him may come down to the fact that they don’t want to head into 2027 needing replacements for both corner outfielders. If the choice comes down to extending the steady and consistent 4-time Gold Glove Happ or the more mercurial but higher offensive upside Seiya Suzuki, the Cubs’ preferred option may be Happ.
MLB writer Eric Cross recently pointed out just how steadily capable Happ has been, noting that the switch-hitter is the only major leaguer over the last three years to deliver “30+ Doubles, 20+ Home Runs, 75+ RBI, 85+ Runs Scored, and 80+ Walks.”
In 2024, Happ signed a 3-year, $61 million extension and, at 31 years of age, a similar deal would be reasonable for both parties, although Happ may push for more years.
So long to Chicago, welcome back for one last year?
Regardless of how well he performs in 2026, catcher Carson Kelly might be a necessary keep for 2027 (if he doesn’t choose to take his services elsewhere via his option). With the frequently-injured Miguel Amaya behind him and nobody close to major league-ready in the minors, the Cubs may need to keep Kelly around.
Relievers Rea, Thielbar, Webb, and Harvey could be back if they perform well in 2026, just because dependable bullpen arms are always a valuable commodity.
Boyd, as mentioned earlier, will likely opt to enter free agency and move on from his guaranteed $15 million in search of more money and more years if his 2026 season is anywhere as good as his 2025 run. If he fizzles in 2026, the Cubs may decline their part of the mutual option. Either way, Boyd may be pitching elsewhere in 2027.
Jameson Taillon and Shota Imanaga, meanwhile, are almost guaranteed goners as their price doesn’t match their expected performance. Given the Cubs’ starting pitching depth, the team could stand to lose both and use that combined $40 million saved to pursue a front-of-rotation replacement.
Suzuki will also likely be gone as he’ll definitely be looking for more than his current $19 million salary and the Cubs may be wary of keeping him onboard for another 5 years at well over $100 million.
So, yes, there will be some big chances coming for 2027. The hope, however, is that at least a couple recognizable names can be brought back.
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