Were the 2025 Cubs a success?
It probably depends on whom you ask.
For some franchises, a campaign of 92 wins, a wild-card series victory and a well-fought, five-game NLDS loss would be dreamland stuff. During the regular season, Chicago’s offense was a legitimate wagon, the only lineup in baseball with six position players worth at least 4.0 bWAR: Nico Hoerner, Dansby Swanson, Ian Happ, Pete Crow-Armstrong, Michael Busch and Kyle Tucker. Wrigley Field, per usual, was packed and rocking for most of the summer as the Cubbies reached October for the first time since 2020 and won their first playoff game since 2018. There was a lot to like.
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Yet at no point in the second half did the Cubs feel like legitimate World Series contenders. The gap between them and the eventual champion Los Angeles Dodgers was gargantuan. Milwaukee comfortably took the division crown. Kyle Tucker, for whom the Cubs traded away a haul last winter, was injured and underwhelming down the stretch and into the postseason. Chicago’s pitching was quite obviously substandard. There was a lot for fans to gripe about.
And halfway through the offseason, there still is, as president of baseball operations Jed Hoyer has done little this winter to quiet the noise. Because while the Cubs have signed more free agents so far this winter (6) than any other team, none of those additions is a true needle-mover. Five are one-year deals. Four are relievers. One was retaining Shota Imanaga on a qualifying offer. In short, the Cubs are not better today than they were the day they lost the NLDS.
Here are the three major questions that will define the rest of their offseason.
1. Will they try to replace Kyle Tucker?
That the Cubs seem entirely content to let Tucker, the market’s consensus top free agent, leave town remains one of this winter’s most underrated developments. Chicago parted with significant pieces to acquire him a year ago, yet the team appears to have zero interest in retaining his services moving forward. That says something about Tucker’s profile and the Cubs’ financial stinginess.
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With Tucker’s departure a foregone conclusion, the Cubs will need to replace that production somehow. Because for all the consternation over Tucker’s relatively underwhelming walk year, the 28-year-old posted an .841 OPS, banged 22 homers and won a Silver Slugger. Those types of players, as will soon be showcased by Tucker’s enormous contract, do not grow on trees.
At present, Chicago seems content to fill the void internally. Outfielder Owen Caissie, a 23-year-old who struggled in a brief, 12-game ristretto, has enormous power and prospect pedigree. That should earn the rookie a sustained look in right field at some point. The same is true for top prospect Kevin Alcántara. Seiya Suzuki DH’ed for most of 2025 but could slide back into right in order to give positionless rookie Moisés Ballesteros some DH at-bats.
In Moneyball parlance, Hoyer and Co. will seek to replace Tucker in the aggregate. That’s a reasonable strategy, given the glut of internal options and the holes on the pitching side.
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2. How will they reinforce the rotation?
Chicago’s 2025 pitching staff was far from a catastrophe. The quintet of Matthew Boyd, Cade Horton, Shota Imanaga, Jameson Taillon and Colin Rea was capable, sufficient and, as a unit, right around league average. Horton, in particular, was a revelation. The rookie dominated for the Cubs down the stretch, and his absence due to injury in October played a significant role in Chicago’s NLDS exit. As volatile as pitching can be, Horton looks like a real frontline arm.
Behind him, however, there are myriad questions. Boyd, a first-time All-Star at 34, was a wonderful story but ran a 4.63 ERA after the break and didn’t reach five innings in any of his three postseason starts. In fact, not a single Cubs pitcher worked past the fifth in the team’s eight playoff games. Taillon was effective in his two starts, yet the club clearly didn’t feel confident pushing him. Rea and Imanaga were both utilized after openers.
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Imanaga returned to town on the qualifying offer after a convoluted series of contractual maneuvering, but barring an unforeseen, late-career velocity jump, he’s probably a mid-rotation arm moving forward.
It doesn’t take a professional prognosticator to see that this rotation could use some help. Another frontline arm to pair alongside Horton would work wonders. Thankfully for Chicago, the starting pitching market has been slow-moving. Framber Valdez, Tatsuya Imai, Ranger Suarez and Zac Gallen all remain available. All four would be reasonable upgrades for the Cubs. However, all four will also require a significant financial outlay, the type Chicago has been hesitant to make of late. Speaking of which …
3. Are the Cubs really going to be this cheap?
If the season started tomorrow, the Cubs would enter 2026 with a payroll just over $200 million, good for 11th in MLB. For such a profitable, historic, popular franchise, that is an embarrassingly paltry figure. In no world should the Chicago Cubs trail the Arizona Diamondbacks in big-league spending. Wrigley Field and all the real estate that surrounds it is a piggy bank, yet Chicago’s ownership group continues to operate like small-market paupers.
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The Cubs have gone above the luxury tax just once since tearing down the Bryant-Báez-Rizzo core. That was in 2024, when Chicago surpassed the threshold by less than $3 million. Currently, the Cubs are projected by Spotrac for an outlay $43 million under the tax. Presumably, that should give Hoyer and Co. room to spend big on a free agent or two. However, all reporting out of Cubs World suggests that such a splash is far from a given.
Given the state of Chicago’s roster, that would be a shame.