The Chicago Cubs took a clear step forward in 2025. Then the postseason ended quietly.
So far, their offseason has matched that tone.
With 87 days until the Cubs open the 2026 season at Wrigley Field, the roster looks competitive, but unfinished.
Chicago finished the 2025 regular season 92-70, good for second place in the National League Central, five games behind the Milwaukee Brewers. The Cubs reached October, winning a three-game Wild Card Series against the San Diego Padres before being eliminated by Milwaukee in five games in the Division Series. It was progress, but it also exposed the gap between contending and truly threatening.
That context shapes everything about this winter.
The Cubs have avoided splashy moves, instead focusing on depth and flexibility. They a dded bullpen arms Phil Maton and Jacob Webb, along with left-handers Hoby Milner and Caleb Thielbar, addressing relief depth that became a stress point late in the season. Those are sensible additions. None materially changes the team’s ceiling.
The most consequential development came with Shota Imanaga accepting the qualifying offer. Keeping Imanaga on a one-year deal stabilizes the rotation and prevents a much larger offseason problem from forming. It also preserves long-term flexibility, allowing the Cubs to reassess next winter without being locked into an extended commitment.
But accepting the qualifying offer cuts both ways. The Cubs still need to improve that rotation.
That is why Chicago has been linked to Japanese right-hander Tatsuya Imai, even as the market for starting pitching tightens. Whether it is Imai or another arm, the Cubs remain one meaningful move away from turning a solid rotation into one that can carry them through October.
The same applies to the lineup.
The offense was good enough to win games in the regular season, but it lacked consistency against top-end pitching. They don't seem to be bringing back top free agent Kyle Tucker. So, without a clear impact addition, the burden again falls on internal growth and sequencing — a risky bet for a team trying to close ground on Milwaukee.
The Cubs are close, but the question is how hard they are willing to push while the window is open.
The offseason has not gone wrong, but it has not gone far enough.
