Cubs’ 92-Win Roster Faces Mass Exodus: Tucker, Bullpen Core Hit Free Agency as Steele Sidelined.vc
With Justin Steele recovering from Tommy John surgery, the Cubs’ pitching staff faces a total rebuild as Mitch Keller, Caleb Thielbar, and Drew Pomeranz also hit the market.
CHICAGO — As the dust settles on their 92-win 2025 season, the Chicago Cubs are staring down one of the most pivotal offseasons in recent memory. After a promising playoff run that ended in the NLDS, the front office now confronts a potential roster crisis.
Free agency is officially underway, and ten players from that 92-win roster have elected to test the market, leaving significant holes in the team’s foundation.
Kyle Tucker Headlines the Departures
The biggest name on the list is slugging outfielder Kyle Tucker. His free agency was always expected; it’s the main reason the Houston Astros moved him in the first place, as he was heading toward a massive payday.
However, after a rocky second half with the Cubs, Tucker’s market value may have taken a hit. He didn’t light it up down the stretch, which could give potential suitors pause. Still, elite power bats are rare. The Cubs must now weigh whether his upside is worth the massive risk—and price tag—especially with other pressing roster needs.
Pitching Staff Faces “Crisis” Level Overhaul
If Tucker’s situation is the headline, the pitching staff is the real crisis.
The rotation is already on shaky ground. Justin Steele, the staff’s most reliable starter when healthy, is expected to miss the early part of the 2026 season as he recovers from Tommy John surgery.
Compounding that loss, the bullpen is being hollowed out. Three of the most frequently used arms from 2025—Mitch Keller, Caleb Thielbar, and Drew Pomeranz—are all unrestricted free agents. This trio averaged 64 appearances apiece, highlighting their vital role in the team’s late-inning plans. Should all three sign elsewhere, the Cubs would essentially be starting from scratch.
The depth issues don’t stop there. Michael Soroka, acquired at the trade deadline, landed on the injured list after just one start, making his impact minimal. Aaron Civale and Trevor Rogers also hit the market; both were used sparingly in the playoffs and are likely seeking larger, more consistent roles elsewhere.
Position Players Squeezed Out
On the position player front, the departures of Willi Castro and Carlos Santana were expected.
Castro found himself in a utility role but was ultimately the odd man out. Left field is locked down by four-time Gold Glove winner Ian Happ, and third base now belongs to rookie Matt Shaw, who just wrapped up a Gold Glove-nominated campaign.
Carlos Santana, meanwhile, was a non-factor in the regular season and playoffs. With Michael Busch breaking out as the team’s primary first baseman, Santana’s path to playing time had vanished. Both veterans are expected to find bigger roles with new teams.
A Defining Winter in Chicago
This free agency cycle is a defining moment for the Cubs. The team made significant strides in 2025, but they are now staring down the loss of major contributors at every level of the pitching staff. The front office must act quickly and decisively to avoid taking a step backward.
With holes in the bullpen, uncertainty in the rotation, and questions about replacing a key bat, this winter could be as important as any game the Cubs played in 2025.
