This story was excerpted from Jordan Bastian's Cubs Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
CHICAGO -- The idea was not merely to give Cubs fans a taste of October baseball but to make that stage an annual part of the season. The team’s trip to the postseason last fall was multiple years in the making and something the franchise hopes is the beginning of a new era of winning.
The process of meeting those expectations begins on Wednesday, when pitchers and catchers hold their first official workout at the Cubs’ complex in Mesa, Ariz. Chicago is aiming beyond its Wild Card berth of ‘25. The ballclub wants to win the National League Central and back that up with a longer run in October.
“You want to go through that month and have a blast,” manager Craig Counsell said during Cubs Convention last month. “I think everybody who experienced it [last] year -- the players, specifically -- you felt it. And you felt how special it is. Then you sit there and try to describe it, and you just say the best way is just to be there again. So that’s what we’re trying to do.”
1. All eyes on Bregman
The Cubs made an attempt to sign Alex Bregman prior to last season but fell short in the free-agent bidding process. President of baseball operations Jed Hoyer -- who has admired Bregman from afar for years -- pursued the star third baseman again this winter and got his man with a five-year, $175 million deal.
“Whenever you’re going to make a significant commitment in years and dollars to a player,” Hoyer said, “you have to feel great about the person, about the human you’re investing in. And I couldn’t feel better about that with Alex. People that have spent time around Alex know that he is obsessed with hitting, obsessed with winning.”
Bregman made a strong first impression with his new team with steps he was taking behind the scene both with teammates and staff. He assumes the starting role at third base, joining Dansby Swanson at short and Nico Hoerner at second to form one of the elite defensive units in baseball.
This spring will offer a closer look into Bregman’s impact off the field, especially given the strong reputation he built in Houston and Boston as a leader and mentor. The Cubs did not lack in leadership last year, but one more experienced voice -- not to mention a lengthy postseason résumé -- could benefit a team with a young, emerging core and playoff aspirations.
2. Building the pitching staff
From the rotation to the bullpen, the Cubs have a series of decisions to make throughout Spring Training. The spotlight will be on hard-throwing righty Edward Cabrera -- acquired from the Marlins in a trade package that included Top 100 prospect Owen Caissie -- but there are multiple layers to Chicago’s pitching situation.
Shota Imanaga is coming off a rocky 2025 showing and will be focusing on getting his delivery in order rather than participating in the World Baseball Classic. Cade Horton is coming off a strong rookie tour but is now entering his first full season with the MLB group. With Cabrera onboard, starters Colin Rea, Ben Brown, Javier Assad and Jordan Wicks could be bullpen candidates.
The relief corps has a group of additions (Phil Maton, Hoby Milner, Jacob Webb and Hunter Harvey), plus a few key returnees (notably, Daniel Palencia and Caleb Thielbar). From there the Cubs will need to determine the best path forward with those swingman options and the pile of arms contending for the last spot or two. And it’s possible Chicago is not done with additions.
3. The plan for Shaw
Bringing in Bregman pushed Matt Shaw off third base and into a super utility role. Barring any roster maneuvering to loosen the infield logjam, Shaw can back up multiple infield spots and try his hand at outfield to find more at-bats. Hoerner is locked in at second base but is only under contract through 2026. How the Cubs handle this situation will be an ongoing story throughout the spring and potentially into the season.