The Chicago Cubs went into the offseason with the promise of making waves, but have thus far only managed to make a couple of small ripples.
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Heading into the 2026 season, the team’s needs are very clear. They became crystal clear as Chicago advanced in the playoffs and in the immediate aftermath of their NLDS elimination. The Cubs need a front-of-rotation starter. They need a heaping helping of bullpen talent, with a priority on late-inning arms, to rebuild a relief corps decimated by a mass of outgoing free agents. They would also like to add a bat to at least somewhat replace Kyle Tucker’s offensive contributions.
So far, they haven’t gotten all that far in their talent acquisition efforts.
Actually, up to now, Chicago’s offseason push amounts to two free agent relievers– Phil Maton and Hoby Milner.
But, as the story has gone every other day this offseason, the Cubs are not done.
The Chicago Cubs’ pursuits thus far
Sep 24, 2025; San Diego, California, USA; San Diego Padres starting pitcher Dylan Cease (84) delivers during the second inning against the Milwaukee Brewers at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
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There are still multiple stories circulating in the media regarding the team’s interest in various players and even their attempts to bring some aboard.
The Cubs were reportedly bidders on Dylan Cease before the Toronto Blue Jays produced money that the Cubs wouldn’t match. They were trying to sign closer Devin Williams, until the New York Mets hit the $51 million mark in their multi-year offer. Chicago was also actively interested in Emilio Pagan, Robert Suarez, and Pete Alonso before losing out. They were even informally tied to Ryan Helsley before he signed with the Baltimore Orioles.
The one common factor in all of the above is that the Cubs were unwilling to go to that next level of spending, which is nothing new for those following the team.
Another common factor is that the team seems to be at least moving in the direction of fulfilling their needs.
Alex Bregman and the Pete Alonso tie-in
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
The biggest story tied to the Cubs this offseason, however, is still a developing story– Alex Bregman.
The Cubs’ interest in Bregman makes a ton of sense from several angles. All in all, though, he’s just the kind of old school, multi-facteted player the organization loves and he definitely fits the bill of a bat to replace Tucker’s.
Some are saying that the Cubs’ reported meeting with Alonso had less to do with wanting to acquire the power-hitting first baseman, and more to do with wanting to see what the Alonso-pursuing Boston Red Sox were willing to spend ahead of a possible loss of free agent Bregman.
Jordan Campbell of Cubbies Crib recently offered his take on the Cubs’ talk with Alonso:
“In actuality, it may have been the Cubs trying to get some insight into the money Alonso was being offered by the Boston Red Sox. Not because they wanted to swoop in and top the offer, but because they wanted to get a sense of what Boston would be willing to spend on Alex Bregman.”
And that definitely makes sense since the Cubs are more than fine with Michael Busch at first base.
Pitching is still a priority, though
MLB: Philadelphia Phillies at Miami Marlins Jun 19, 2025; Miami, Florida, USA; Miami Marlins starting pitcher Edward Cabrera (27) delivers a pitch against the Philadelphia Phillies during the first inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images
Patrick Mooney and Sahadev Sharma of The Athletic, meanwhile, are reporting that the Cubs “are still actively looking for a late-game reliever,” despite a market that has shrunk considerably in recent days.
Then, of course, there were the recent reports of the Cubs maybe focusing on possible trades with the Miami Marlins and Washington Nationals for starting pitchers Edward Cabrera and Mackenzie Gore, respectively.
In a best case scenario, they could snatch up the costly Bregman while trading for a more budget-friendly starter with years of team control ahead. That would certainly kill two birds with one gigantic stone, although they’d still be short one late-inning, closer-capable reliever.
Whatever the case, the Cubs need to move fast or be stuck with leftovers, bargain bin buys, and reclamation projects.
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