18 Players Heading Into Free Agency: Who Should The Chicago Cubs Keep for 2027 and Beyond?

Yes, the Cubs should absolutely pick up Assad's $3.3 million club option. He finished the 2026 regular season with a 3.63 ERA in 94.1 innings and carries a 3.47 ERA across 106 career MLB games. His versatility to start, swing, or relieve makes him an easy decision.

Holmes holds a $12 million player option and is expected to decline it and hit free agency. The Cubs traded their top prospect Jefferson Rojas to acquire him, so they are expected to be heavily interested in bringing him back. His 60.7% ground ball rate in 2026 fits perfectly with the Cubs' elite infield defense.

Yes, at just $2.5 million on his club option, Webb is worth retaining despite his brutal final five weeks of the season. He posted a streak of 24.2 scoreless innings earlier in the year and carries a career 3.07 ERA in 315 MLB games. The Cubs just need to make sure he isn't their primary closer come September.

Seiya Suzuki has averaged 25 home runs per season since 2023 and has posted an OPS above .800 throughout his five-year MLB career. Despite his consistent production, early reports suggest the Cubs front office is not interested in getting into a bidding war to re-sign him. The Cubs should try to bring him back, but his future on the North Side is uncertain.

The Cubs should bring back one of the two but not both, and Taylor is the preferred option due to his lower projected cost. He played well after coming over from the Mets at the trade deadline and can cover both corner outfield spots as well as spell Pete Crow-Armstrong in center. Since the Cubs are expected to spend heavily on pitching, a modest deal for Taylor fits their offseason budget better than paying Conforto as a starter.