The Toughest Free Agent Decisions the Chicago Cubs Face Heading Into 2027

David Peterson is a 31-year-old left-handed pitcher who posted a 3.70 ERA and a 49.1% ground-ball rate in 80.1 innings with the Cubs in 2026. He's the youngest of the four pending free-agent starters and his ground-ball tendencies fit perfectly behind the Cubs' elite defense. He's also a former All-Star from 2025, meaning he still has the upside to pitch at a higher level than a typical fifth starter.

It's possible, but only if Happ takes a significant pay cut from his previous three-year, $61 million deal. The Cubs already view him as a platoon bat rather than an everyday player, and the front office is expected to spend most of their offseason budget on pitching. If Happ is willing to accept a short-term, team-friendly contract, the Cubs would be interested.

Despite a solid end to the 2026 regular season, Imanaga couldn't be trusted to start in the playoffs for two straight years due to concerns about giving up home runs. That back-to-back postseason issue appears to have pushed the Cubs toward moving on from the left-hander.

Civale would need to fully commit to being a full-time reliever, something he has publicly resisted since he prefers to start. He's been outstanding in the bullpen for the Cubs, posting a 1.72 ERA in 36.2 innings in 2026 and a 2.42 ERA over two years as a reliever, so the Cubs would bring him back under that condition.

Kelly has a $7.5 million mutual option with a $1.5 million buyout, and he's expected to decline the option to test free agency. The Cubs love what Kelly has brought over two years, but with most of their offseason budget likely going toward pitching and a crowded catcher market in play, a reunion is considered unlikely.