The Chicago Cubs are staring at the same problem again this winter: Milwaukee is still ahead, and the gap is still too wide. Fourteen games separated the Cubs from the Brewers in 2026, and now the defending World Series champions sit there as the team Chicago has to chase.
That chase comes at a tricky moment. The Cubs’ window is still open, but it already feels like it could be narrowing.
Pete Crow-Armstrong is the obvious centerpiece, yet the rest of the roster comes with plenty of questions. Alex Bregman is getting closer to the wrong side of 30, Dansby Swanson’s bat is starting to drag, Nico Hoerner’s uneven 2026 season raised a warning sign, and Michael Busch didn’t make the jump the Cubs were hoping for last year.
With a number of 2026 contributors headed for free agency, this offseason has the feel of a turning point. The Cubs are going to have a new core in 2027, but the expectation remains the same: close the distance on Milwaukee. And with the MLB lockout looming, the front office has to move fast.
The first priority has to be landing a true front-line starter, even if Tarik Skubal is the dream that may not fit the Cubs’ spending habits. Chicago may want him, but there’s little in the club’s history to suggest it will go all the way to the top of the market for the best arm available.
Still, the Cubs can’t come out of the winter without an ace. If they do, catching the Brewers in 2027 starts looking unrealistic.
Michael King, projected at four years and $100 million, fits the bill because he keeps the ball on the ground and can still miss bats.
A second move could give them more than one shot at solving the rotation. Sonny Gray, projected for two years and $52 million, offers a different path than Skubal and fits the kind of approach Jed Hoyer has tended to prefer.
Rather than one massive swing, the Cubs could spread the money around and come away with both King and Gray for less than the cost of one elite target. Gray’s 2026 line with the Red Sox - a 2.72 ERA in 29 starts - would give Chicago another high-end option, and one with more upside than Clay Holmes.
The Cubs also need to stop running out of pitching when it matters most. That problem showed up again over the last two seasons, and even after a deadline attempt to patch things up this past summer, Craig Counsell still had a tough time lining up his rotation once the playoffs arrived.
Injuries are part of that story, but the answer is to build more depth and better depth. David Peterson, projected at two years and $22 million, would help there.
Even if he doesn’t repeat his 2027 success with the Cubs, he still gives them a usable floor as a swingman out of the bullpen.
Then there’s the outfield, where the Cubs may not need a splash but do need a bridge. Masataka Yoshida makes sense as that stopgap.
The Red Sox have more outfielders than they need, and the expectation is that Yoshida will be elsewhere in 2027. He’s in the final year of a five-year, $90 million contract, and he could hold down the position until Josiah Hartshorn and Kane Kepley are ready.
He would also be a more established answer than Matt Shaw or Pedro Ramirez in the outfield, and his arrival could even nudge Shaw into trade territory if the Cubs want to use him to land a cost-controlled pitcher.
In Other News...
Cubs Could Revisit A Familiar Rotation Move This Winter
Jed Hoyers winter pitching plan appears to be taking shape, and it does not sound like the Cubs are preparing to chase the biggest name on the market. Instead, Chicago is expected to look for starting pitchers who come at a more manageable price, with an eye toward arms that either miss bats or keep the ball on the ground. It is the kind of practical approach that fits the way the front office has operated, especially with the rotation still needing stability heading into next season.
One familiar option could be Shota Imanaga, who spent his entire MLB career with the Cubs and accepted a qualifying offer for 2026. The left-hander turned in a solid 2025 season, but the Cubs did not use him in their playoff games, and there are still some concerns about his home run issues. Even so, he remains a possible fit if the price is right, though Chicago seems wary of going too far to bring him back. [Read more 🡒]
Ben Brown News Just Made The Cubs Rotation Problem Even Worse
Ben Browns offseason took another turn when the Cubs right-hander underwent a procedure to address the recurring neck issue that cut short his 2024 season. The surgery pushes back the start of his throwing program, but the organization is treating it as a step toward getting him fully right rather than a setback that changes the long-term outlook.
Cubs general manager Carter Hawkins said the team opted for surgery with the goal of helping Brown recover completely, and the expectation is that he should be ready to pitch early in the 2027 season. For a rotation that already has plenty to sort through, losing any time from a pitcher the Cubs were hoping to count on only adds to the uncertainty heading into the year. [Read more 🡒]
Cubs Trade Debate Starts With One Tempting Move Hoyer Should Avoid
The Cubs are headed into the GM Meetings with the same familiar shopping list: help for the starting rotation and another bat in the outfield. Any serious trade discussion around Chicago has to start with those needs, and the early speculation is already circling a few big names that would force Jed Hoyer to weigh upside against cost. Nathan Eovaldi, CJ Abrams and Spencer Strider each represent a different kind of swing, with varying levels of fit and risk for a club trying to stay competitive without emptying the cupboard.
Of the ideas being kicked around, the one tied to Strider is the kind of temptation that can quickly become a trap if the price climbs too high. Chicago can use impact, but it also has to be careful not to chase the loudest name simply because the rotation needs a jolt. The Cubs will have options to explore in the coming days, and the real challenge is figuring out which path actually improves the club without creating a bigger problem somewhere else. [Read more 🡒]