Chicago Cubs fans, at this point, are certainly hip to the routine when it comes to their team’s talent acquisition patterns and to the promising buzz that almost always precedes a letdown.
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First, the internet is lit up with rumors, gossip, and promises that, this time, the Cubs will be “all-in” when it comes to big, bold roster moves and talent pickups.
Then, as free agents get scooped up and major trades fail to materialize, the Cubs fandom becomes increasingly disheartened and frustrated. When the dust settles, the Cubs’ haul generally consists of bargain buys and reclamation projects and talk about “right fits” and value for the money invested.
This happened twice just last season as an uncharacteristically bold winter trade with the Houston Astros for Kyle Tucker and two-year budget gambles on Matthew Boyd and Carson Kelly existed alongside a cynical salary dump of Cody Bellinger, a roll-the-dice trade for Astros’ washed-out former closer Ryan Pressly, and a failure to pull the trigger on a Jesus Luzardo trade with the Marlins.
Then, with the supposedly mega-aggressive team in need of some obvious roster reinforcement for a playoff push ahead of the trade deadline, they whiffed on a major acquisition. Rather than the starting pitcher and experienced closer they needed, they picked up some middle-tier bullpen help and a utility man.
So, with this pattern in mind, let’s take a realistic look at what fans can expect from the Cubs for the rest of this offseason. And, no, sorry, they’re not getting Alex Bregman or Tastuya Imai and they’re not re-signing Kyle Tucker.
Zac Gallen
David Frerker-Imagn Images
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Despite their frugal, mega-conservative mindset, the Cubs have to know that they’ll be absolutely raked over the coals if they don’t make some kind of biggish splash this offseason. And the easiest route to that splash is through starting pitching.
Japanese import Tatsuya Imai is just too much of a gamble for too long of a time for the Cubs’ tastes. If the contract years go down and the overall price tag gets more economical, maybe Chicago will take a swing. Until then, nope.
Other top free agent starters also present too much risk for their respective asking prices. Ranger Suarez has had back issues. Framber Valdez has some clubhouse concerns. Dylan Cease and Michael King are already off the market. A big trade, meanwhile, seems unlikely because, quite frankly, other needy teams just have a deeper well of prospects than the Cubs do.
So, Zac Gallen, with his more modest stats and more modest contract projection, should be the guy the Cubs pull in.
Make no doubt about it, the 30-year-old Gallen, rebounding from an “off” 2025 (13-15, 4.83 ERA), would be a welcomed addition to the starting rotation. He’d be the workhorse the Cubs need amid a crew of starters with legit durability issues. And, from a business perspective, he’d be the most team finance-friendly option from this year’s list of high-end free agent starters, with contract projections ranging from 2-years at $45-$54 million to 4-years at $76 million.
The ideal fourth outfielder
Oct 6, 2025; Philadelphia, Pennsylvania, USA; Philadelphia Phillies left fielder Max Kepler (17) runs to third base after hitting a triple against the Los Angeles Dodgers in the eighth inning during game two of the NLDS round for the 2025 MLB playoffs at Citizens Bank Park. Mandatory Credit: Bill Streicher-Imagn Images
If the Cubs aren’t getting Alex Bregman to fill Kyle Tucker’s lineup slot and are intent upon leaving right field to Seiya Suzuki and/or rookie Owen Caissie, they would do well to pick up a top notch fourth outfielder.
Outgoing Phillies free agents Max Kepler and Harrison Bader fit perfectly into the Cubs’ needs.
Not only could both assume full-time duties in right field if needed, but they could also provide much-needed relief to left fielder Ian Happ and center fielder Pete Crow-Armstrong without any major defensive or offensive drop. With Happ’s contract set to expire next season, both could also be an important plan B option to a sudden vacancy in left field.
In terms of ability and skill set, Kepler and Bader profile similarly and are at similar stages of their careers. Both are also projected to go for around $11-$12 million per season on a two or three-year deal. The Cubs would just have to decide whether they’d prefer the right-handed hitting Bader or the lefty Kepler.
The focus on the outfield would keep Matt Shaw at third base and, possibly, open up the possibility of trading away young talent Caissie or Moises Ballesteros for more pitching help.
The low-risk, high-yield gamble
Cubs president Jed Hoyer loves reclamation projects at a budget price and pitcher Mike Clevinger could be a reasonable low-risk add-on to a pitching staff in need of depth.
The 35-year-old right-hander has a history of injury, but also a history of success before the physical issues dragged him down. Successful neck surgery at the end of 2024 didn’t lead to immediate success on the mound for the 8 games he managed to play with the White Sox in 2025, but it’s felt that a full-time move to the bullpen will help keep him healthy and productive.
When right, Clevinger is a versatile pitcher with respectable strikeout capability and a run of four straight successful years (2017-2020) as a starter with a combined 2.96 ERA during that period of time. Fitting him into a swing man role on a cheap one-year contract would be a trademark Cubs move.
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