The Cubs won’t have many players entering free agency this offseason. Of course, the big one is Kyle Tucker, who is set to command a contract upward of $350 million. Outside of him, though, the list is very small. 

While we wait and see whether the Cubs will pick up club options on Shota Imanaga, Andrew Kittredge, and Colin Rea, Chicago is only set to lose 11 players to free agency as it stands now. The list is as follows: 

The good news is that the Cubs aren’t expected to lose many free agents. However, there are a few players listed above whom the front office must re-sign this winter. 

The No. 1 player the Cubs have to re-sign in free agency is Keller. The right-hander had a breakthrough campaign in 2025, finishing with a 2.07 ERA and 75 strikeouts across 69 ⅔ innings pitched. He was arguably the best arm in Chicago’s bullpen this past season. 

The Cubs signed him to just a one-year, $1.5 million contract last offseason, but the right-hander is likely going to want a multi-year deal this offseason. Although the front office doesn’t usually give out multi-year deals to relievers, Keller has to be the exception. 

He was reliable as the setup man, and this year wasn’t just a fluke.  His expected batting average against (.204), strikeout rate (27.2%), hard-hit rate (30.6%), and chase rate (26.9%) all ranked toward the top of the league. 

The Cubs made a small trade in late April of last season to acquire Pomeranz from the Mariners. It was a low-risk, high-reward pickup for a pitcher who was a former All-Star earlier in his career. 

That low-risk pickup worked in the Cubs' favor, considering Pomeranz was one of the most consistent arms in Chicago’s bullpen. He finished the year with a 2.17 ERA and 57 strikeouts across 49 ⅔ innings pitched. 

Given how well Pomeranz pitched during the 2025 season, the Cubs need to re-sign him. He is only projected for a one-year, $5 million contract in Jim Bowden’s Top 50 free agents article, and that seems like an easy re-sign for the front office.

Thielbar showed last year that his age isn’t slowing him down just yet. At 38 years old, the southpaw had arguably the best season of his career. He maintained a 2.64 ERA and 56 strikeouts in 58 innings of work. 

More importantly, he was the left-hander that Craig Counsell went to in high-leverage slots. For that reason, re-signing Thielbar to a one-year contract is almost a must for this Cubs team this offseason. 

He was fantastic out of the bullpen this past season, with a 31.8% hard-hit rate, a 32.2% chase rate, and an expected 2.43 ERA. Those metrics are good enough to bring him back for another season.