The Chicago Cubs could whiff on every big name this offseason and make zero true impact moves before the start of the 2026 season. It’s entirely possible that the team just won’t be bold enough to win a bidding war for Alex Bregman or pick up a front-of-rotation starter. It’s also quite reasonable to believe that they just won’t have the juice to pull off a major trade.
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If that happens, there will be hell to pay for the Ricketts family ownership and the team’s front office– because, if the Cubs don’t win big this season and lay team cornerstones for the future, there could be a huge competitive drought coming very soon.
The need to win and build right now
Chicago Cubs Chairman Tom Ricketts (R) smiles next to Chicago Cubs President of baseball operations Jed Hoyer (L) before a baseball game between the Chicago Cubs and Cincinnati Reds at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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Basically, most of the core veteran leadership of the team is set to hit free agency at the end of the coming season (Ian Happ, Nico Hoerner, Seiya Suzuki, Carson Kelly, Jameson Taillon, Matthew Boyd, Shota Imanaga, Colin Rea, Caleb Thielbar) and most, if not all, will probably be moving on. That’s almost a third of the team, half of the starting position players and 60% of the starting rotation.
There’s a legit belief that Chicago, despite having some young talent scattered across the roster, has a “this-year-only” window to make a true run at a championship before reality pulls them back to the middle of the MLB pack. And not only does the team need to put a competitive squad over the top with an impact move or two, they also need for those impact moves to lay a foundation for winning beyond 2026.
That’s why this offseason is so important and why there should be an extra degree of frustration in the fact that the Cubs seem as conservative and as lacking in urgency as ever.
The (slow) offseason thus far
Sep 23, 2025; Arlington, Texas, USA; Texas Rangers pitcher Jacob Webb (71) throws to the plate during the fifth inning against the Minnesota Twins at Globe Life Field. Mandatory Credit: Raymond Carlin III-Imagn Images
Up until now, amid buzz of high-minded targets, Chicago’s entire offseason talent haul consists of middle relievers Phil Maton, Hoby Milner, and Jacob Webb, alongside backup first baseman Tyler Austin and the one-year re-signing of pitchers Imanaga and Thielbar.
And while it’s important to address the hollowed-out bullpen, there are much bigger concerns to address on this roster.
One thing in need of immediate attention is the outgoing Kyle Tucker and how to replace what he brought to last season’s offense as a middle-of-the-lineup linchpin.
The Cubs didn’t seem very interested in trying to extend the four-time All-Star right fielder during the season. They’ve seemed even less interested in negotiating a return now that he’s on the open market.
The apparent hard pass on a free agent Tucker has infuriated many, especially since there seems to be no real backup plan to replace his presence beyond in-house options.
Conservative Cubs falling behind, again
Sep 20, 2025; Tampa, Florida, USA; Boston Red Sox third baseman Alex Bregman (2) runs to first base after hitting an rbi single against the Tampa Bay Rays in the fifth inning at George M. Steinbrenner Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images
Mark Powell of Fansided recently expressed his disregard for the way the Cubs go about their business as a team, particularly related to letting Tucker walk without much apparent concern:
“The Cubs operate their budget as if they’re the Guardians and Tigers…The Cubs are almost guaranteed to lower payroll next season, and will let Kyle Tucker walk in the process. Tucker is the kind of player serious contenders would build around. Instead, all we get from Ricketts and [Cubs president] Jed Hoyer is a shoulder shrug.”
Free agent third baseman Alex Bregman has been mentioned as an ideal lineup replacement for Tucker and as someone who could be the kind of leader the team needs for the future. However, their pursuit of Bregman seems tempered by an unwillingness to spend beyond their comfort level– especially with a younger (and much cheaper) Matt Shaw currently slated for the hot corner.
Jordan Campbell of Cubbies Crib has talked up this Cubs/Bregman/Shaw dynamic and how Chicago’s conservative mindset is possibly leading them to a more passive position when it comes to the free agent third baseman.
Per Campbell:
“That is why, in the background of the rumors surrounding the Cubs this offseason, there’s been the impression that they are enamored with Alex Bregman. And yet, because they have Shaw at third base, the Cubs seem more comfortable letting Bregman’s market fall to them instead of forcing the issue.”
The team’s “fall back and see” lack of urgency could also cost them the starting pitchers they’ve reportedly been eyeballing. It’s already cost them Dylan Cease, who they lost to the high bid of the Blue Jays, and a handful of the top closers on the free agent market.
If the Cubs walk into the 2026 season with nothing to show for a critical offseason but some middle relievers and a couple of budget reclamation projects, tough times may be ahead.
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