Grading the Chicago Cubs' 2025-2026 Offseason

[RandallPnkFloyd]

Image courtesy of © David Banks-Imagn Images

With spring training games mere days away, the 2026 season is officially underway for the Chicago Cubs. Last year's group carried plenty of intrigue with Kyle Tucker in the mix and the emergence of Pete Crow-Armstrong among the storylines, but it was always a team that felt incomplete. This winter, however, Jed Hoyer and company took measures to ensure that the 2026 roster would look a bit more robust than its immediate predecessor. It wasn't a perfect offseason, of course; it still feels like one or two more moves could have really solidified things from the jump. Nevertheless, it's a roster whose prospects in the upcoming season offer something a little more encouraging than what came before it.

Cubs' Offseason Free Agent Signings

• RHP Phil Maton (two-year, $14.5 million)
• LHP Hoby Milner (one-year, $3.75 million)
• LHP Caleb Thielbar (one-year, $4.5 million)
• 1B/OF Tyler Austin (one-year, $1.25 million)
• RHP Jacob Webb (one-year, $1.5 million with 2027 club option)
• RHP Hunter Harvey (one-year, $6 million with 2027 mutual option)
• 3B Alex Bregman (five-year, $175 million)
• RHP Shelby Miller (two-year, $2.25 million)

There was a certain onus on the front office to be extremely active this winter. For a while, though, much of the action took place almost exclusively in relief. Hoyer and general manager Carter Hawkins were tasked with replenishing a pitching staff that lost Brad Keller, Taylor Rogers, Aaron Civale, Michael Soroka, Drew Pomeranz, and Ryan Brasier to free agency and traded Andrew Kittredge back to Baltimore early this winter. Rather than undergo the more typical process of building the relief corps out of reclamation types, the focus was on veteran arms. Each of Maton, Milner, Webb, and Harvey bring a veteran dynamic from both sides of the mound while Thielbar continues to be a reliable presence set forth by a strong showing with the Cubs in 2025. Miller's deal, however, puts an eye on 2027 considering he's set to miss the upcoming season while he recovers from Tommy John surgery. This updated collection of relief arms comes in addition to the typical smattering of minor-league deals and waiver claims. 

This talk of relievers buries the lede, however. The most impactful move of the winter was the team's signing of Alex Bregman to a five-year contract. A team that lost Kyle Tucker in free agency — and never really had any ambition of retaining his services for the long term — needed to produce impact offense from somewhere. In Bregman, they get a gap-to-gap hitter who doesn't strike out. To say nothing of the veteran presence he is reported to add to any clubhouse environment. He was one of only two major-league signings the team made to fortify their lineup this winter, as Tyler Austin returns from a lengthy stint in Japan to serve as a right-handed compliment to Michael Busch and, perhaps, occasional designated hitter.

While not true free agents, it also seems worth noting here that the team re-signed Colin Rea to a one-year deal with a club option for 2027 while Shota Imanaga returned on the qualifying offer after both sides declined their respective 2026 options.

Cubs' Offseason Trades

• Acquired cash from the Orioles for RHP Andrew Kittredge
• Acquired RHP Edward Cabrera from the Marlins for OF Owen Caissie, SS Cristian Hernandez, and IF Edgardo De Leon

As busy as things might've been on the free agent front, the trade circuit had nary a whisper as to the team's intentions this winter. The Kittredge move happened early, as the team wasn't inclined to pay the $9 million owed to him for 2026. In Cabrera, however, the Cubs made as impactful a move as they could have hoped for. Long-rumored to have interest in a starting pitcher with frontline stuff, the Cubs brought in Cabrera to sit toward the front of the team's rotation. They lost some of their medium-term stability in doing so by trading Caissie (considering the impending free agent status of each of both Ian Happ and Seiya Suzuki), but acquired exactly the profile for which they'd been searching for at least a couple of years.

Cubs' Offseason Grade

Similar to the 2024-2025 offseason, the Cubs did not have a lot of questions on their roster in need of answers. Save Tucker, much of last year's starting lineup remained intact, while the rotation carried over plenty of the volume from 2025 into the winter, especially once each of Rea and Imanaga were retained in their respective ways. Nevertheless, the Cubs remained a team starved for impact. They needed some on offense to replace Tucker, and perhaps beyond. They lacked the sort of dynamic presence in their rotation outside of Cade Horton. While there's an argument to be made that they could have gone further (especially on the offensive side), the fact that they were finally willing to open the payroll to an addition like Bregman and invest in an arm like Cabrera — in addition to the dramatic shift in process on the bullpen front — signals a shift in the somewhat stagnant modus operandi we've seen from the organization over the last few years. A B+ feels more than earned.

Verdict: B+

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