The Chicago Cubs are entering a pivotal year in 2026.

Outside of potentially losing Kyle Tucker and a few bullpen arms this offseason, most of the Cubs’ roster stays intact. The rotation will still feature pitchers like Matthew Boyd, Shota Imanaga, Cade Horton, Justin Steele, and Jameson Taillon, and eight of the nine starting hitters from last year are returning.

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However, that won’t be the case after the 2026 season. That’s because several key players on this Cubs team will be free agents following next year. Players like Imanaga, Boyd, Taillon, Seiya Suzuki, Ian Happ, and Nico Hoerner will all enter free agency.

With these players on the last year of their deals, let’s look at the likelihood of these players still being with the team in 2027.

Nico Hoerner

Hoerner was simply the Cubs’ best player in 2025. He hit .297 with seven home runs, 29 doubles, 61 RBI, and 29 stolen bases across 156 games while also playing Gold Glove defense at second base. That helped him earn a team-leading 6.2 WAR.

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So, it would be highly unlikely to see the Cubs not sign Hoerner to an extension either this offseason or next offseason. He is so valuable to this team and has become a fan favorite among all Cubs fans.

The Cubs won’t let him go anywhere.

Seiya Suzuki

Suzuki has improved offensively in each of his first four years in the Major Leagues. He hit 20 home runs and drove in 74 runs in 2023, hit 21 home runs and drove in 73 RBI in 2024, and then broke through in 2025 behind a 32-home run, 103-RBI campaign.

Given Suzuki’s power potential in this Cubs lineup, there’s a solid possibility that the Japanese slugger will remain with Chicago beyond the 2026 season. He will be arbitration-eligible after this season, so fans shouldn’t worry about him leaving.

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Suzuki should be here to stay in 2027.

Ian Happ

It really is a toss-up whether the front office will re-sign Happ next offseason. The longtime Cub is the longest tenured player in the organization and has been with the team since the start of the 2017 campaign.

However, Happ will be 32 years old at that point and hasn’t been the most consistent hitter at the plate at times. The Cubs could offer him a generous multi-year contract to remain with the team, but since this could be the last big contract of his career, he could look for that elsewhere.

Shota Imanaga

Imanaga returning to the team after the 2026 season is truly a 50-50% likelihood. If he continues to struggle on the mound, there is no way the Cubs would be willing to bring him back for another year.

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If he pitches like his 2024 rookie self, though, the front office would be more willing to sign Imanaga to a multi-year contract. So, this is a prove-it year for the southpaw. He will be playing on the $22.025 million qualifying offer this season.

Jameson Taillon

After struggling in his first year with the Cubs in 2023, Taillon has had back-to-back successful campaigns on the mound. He finished with a 3.27 ERA across 165 ⅓ innings in 2024 and then had a 3.68 ERA in 129 ⅔ innings pitched last year.

Considering how well Taillon has pitched in recent seasons, his asking price might be higher than what the Cubs are willing to pay him next offseason. He will be 35 years old and could be asking for the final big contract of his career.

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Matthew Boyd

It would be hard to imagine Boyd coming back to the Cubs after the 2026 season. If he has another All-Star-worthy campaign, then the left-hander will likely ask for a nice payday the following offseason.

If his numbers regress a bit from 2025, it would be surprising for the Cubs to give him another contract. He would be 36 years old once the 2027 season begins, and his best days would probably be behind him.