2025-26 MLB Offseason Recap: Chicago Cubs

Even though the Cubs had their season cut short by the Brewers, Chicago broke a five-year playoff drought and delivered postseason baseball back to the Second City. Heading into 2026, what do the Cubs have for an encore? Whatever that may be, the Cubs will have a very different look heading into the year.

Additions

• 1B Tyler Austin
• 3B Alex Bregman
• SP Edward Cabrera
• RP Hunter Harvey
• RP Phil Maton
• RP Shelby Miller
• RP Hoby Milner
• RP Jacob Webb

The Cubs went with multiple options at the hot corner last season, including then-rookie Matt Shaw and former Rule 5 Draft pick Gage Workman. For 2026, the Cubbies will have a more permanent option.

Alex Bregman, the former Gold Glove winner, joined the Cubs after what was an impressive injury-shortened season with the Red Sox. Bregman brings a lengthy list of accolades and assets, including a great eye, ability to adjust at the plate, consistent contact, power, and a good, rangy glove at third base.

He’ll also be relied upon to fill a big hole left behind by a former teammate he had with Houston.

The other notable acquisition was Edward Cabrera, the high-upside arm who was picked up in a January trade with the Marlins.

As we noted when the trade went down, Cabrera was a different pitcher last year. He did spend time on the IL last season, which was a problem throughout his career. But with Cabrera, he really tried to mix up the types of looks he gave to hitters last season. The curveball usage rate jumped, and the velocity was good overall.

With three years of team control, the Cubs may have done very well here, provided that Cabrera’s health holds up.

Tyler Austin, a formidable power hitter with Yokohama in Japan, signed an MLB deal with the Cubs over the winter. That contract gave the Cubs a nice platoon option, as Austin is a right-handed-hitting first baseman who could complement Michael Busch well.

However, a knee operation in February will cost him significant time this season.

Aside from those additions, the bullpen received a facelift. Phil Maton’s high-spin repertoire is now on the North Side, while Hunter Harvey will look to (hopefully) bring an electric fastball to the Cubs. Hoby Milner, one of the funkiest relievers in all of baseball, also signed with the Cubs.

Losses

• RP Ryan Brasier
• OF Owen Caissie
• INF/OF Willi Castro
• SP/RP Aaron Civale
• RP Brad Keller
• RP Andrew Kittredge
• C Reese McGuire
• RP Drew Pomeranz
• RP Taylor Rogers
• 1B Carlos Santana
• SP Michael Soroka
• OF Kyle Tucker
• 1B Justin Turner

Kyle Tucker’s stint in Chicago only lasted one year.

The Cubs acquired Tucker in the 2024-25 offseason with the idea that he would be the missing piece for a championship team. He certainly had a positive effect on the rest of the Cubs’ lineup, protecting Michael Busch and Seiya Suzuki, something that his old teammate from Houston will have to do in 2026.

However, Tucker had his troubles at the plate in various stretches of the season, including in the postseason. Yes, the Cubs made the playoffs last year, and it would be unwise to state that Tucker didn’t play a role in that. However, that trade cost the Cubs a good young piece in Cam Smith.

Chicago will hope that trading Owen Caissie won’t be a bad move. Caissie was part of the package that helped the Cubs land Cabrera. It virtually assures the Canadian a path to playing time moving forward, even though he likely would have received a shot with the Cubs in 2026 with Tucker gone.

As for the rest of the losses, the bullpen will look very different.

Drew Pomeranz (Angels) and Brad Keller (Phillies) went from fliers to key relievers for the Cubs last season. Both netted themselves respectable Major League deals over the winter.

Andrew Kittredge, who spent the last few weeks of the regular season as interim closer thanks to an injury to Daniel Palencia, was traded back to the Orioles in a salary dump deal. Kittredge had a $9MM club option for 2026 that Baltimore took on.

Chicago also opted not to return midseason acquisitions Willi Castro, Carlos Santana, Aaron Civale, Taylor Rogers, and Michael Soroka.

Overview

This team is firmly in win-now mode, although it is worth noting that the Cubs’ window should be open for some time. Thanks to players like Pete Crow-Armstrong, Matt Shaw, Cade Horton, and hopefully soon, Jonathon Long and Moises Ballesteros, this team should have that window open for a while.

Adding Bregman, a difference-maker with the Astros, as well as pitching depth, could be a strong step forward. But it won’t be easy in the NL Central this year.