The Cubs may have liked their chances in the Tarik Skubal chase once upon a time, but that idea is fading fast. According to Sahadev Sharma’s report for The Athletic, Chicago “appear unlikely to enter the bidding war for two-time Cy Young Award winner.”
That retreat says plenty about where the Cubs are headed this winter. The organization is staring at a major rotation rebuild, and that reality makes a run at one elite starter feel more like a luxury than a plan.
Shota Imanaga, Kevin Gausman, Clay Holmes, Matthew Boyd, David Peterson, Colin Rea, and Aaron Civale - all seven of whom were on the Cubs’ Wild Card Series roster - have all hit free agency. At the same time, Chicago still has corner outfield questions hanging over the roster, with Ian Happ and Seiya Suzuki needing to be replaced or re-signed.
In other words, this isn’t a one-move offseason. It’s a patch-the-roof, fix-the-walls, and maybe replace the plumbing kind of winter.
That’s why the Skubal situation looks so different from the outside. If the Cubs were one arm away from catching the Brewers, maybe they could justify going all-in on one of the best pitchers in the game.
But they aren’t. They need at least two starters, possibly three, just to get to a workable rotation for Opening Day.
Add in the outfield issue, and the math gets ugly in a hurry.
The free-agent market offers some names Chicago could circle back to, including Gausman and Holmes, while Freddy Peralta, Trevor Rogers, and Michael King are also out there. But trying to land Skubal and another arm - or two - while also solving the corner outfield problem would be a tall order.
That’s the bigger story for the Cubs: the offseason is about replacing what’s leaving, not adding enough to make a clean jump toward the Brewers. The gap between the two clubs was 14 wins this year, and Chicago’s current challenge is figuring out how to make up ground while rebuilding at the same time.
Milwaukee, meanwhile, is in the far more comfortable position. Over the last four seasons, the Brewers have won four straight division titles and five of the last six, knocked off the Cubs in the 2025 NLDS, and then beat the San Diego Padres in this year’s NLDS after Chicago was bounced in the Wild Card Series. The Brewers also celebrate their World Series win and expect a largely unchanged roster back for the 2027 campaign.
That’s the contrast here: one club is scrambling to cover holes, and the other is mostly waiting for a familiar core to keep rolling. For Brewers fans, that’s a pretty good place to be.
In Other News...
Brewers Face A First Base Decision That Could Shape 2027
The Brewers are already looking ahead at first base, where Jake Bauers may not be part of the picture much longer and the front office has to weigh both the immediate fit and the longer-term plan. Milwaukee has a few internal possibilities, including prospect Andrew Fischer, but the short-term preference appears to lean toward a more established bat who can help stabilize the position while the club keeps its bigger roster picture in mind.
One name in the mix is Nathaniel Lowe, a veteran with a track record on multiple teams and enough offensive credibility to make sense in a shared role with Andrew Vaughn. Lowe also brings slightly better defensive numbers, which matters for a Brewers team trying to squeeze value out of every spot on the diamond, and the decision could end up shaping how Milwaukee handles first base well beyond this winter. [Read more 🡒]
Brewers Face New Pressure In Bullpen Reunion Pursuit
The Brewers are heading into the winter with the unusual comfort of bringing back most of the roster from their 2026 World Series run, but the bullpen could still look different by Opening Day. Free agency and possible trades may leave a few late-inning spots open, which puts extra weight on every move Milwaukee makes as it tries to preserve the depth that helped carry it to a title.
JoJo Romero sits near the center of that conversation. The left-hander was part of the championship roster and is now available on the market, making him a natural fit for a reunion if Milwaukee wants to keep familiar pieces in place. The challenge is that the Brewers are not operating alone, and the search for bullpen help could turn into a bidding contest before the offseason settles into its rhythm. [Read more 🡒]
Brewers Young Core Just Got Overlooked In A Race That Mattered
The Rookie of the Year race in 2026 had plenty of familiar names at the top, but it also left Milwaukee with a little reason to wonder where its young core fit into the conversation. Sal Stewart took the National League honor for Cincinnati, with Cardinals second baseman J.J. Wetherholt and Mets right fielder Carson Benge ending up as the finalists, while the Brewers group of Logan Henderson, Cooper Pratt and Luis Lara stayed on the outside looking in despite turning in strong seasons.
Henderson at least drew some support in the voting, which says something about how close Milwaukee came to getting a bigger foothold in the race. The broader picture is still a reminder that awards ballots do not always line up neatly with what a club sees on the field, and for the Brewers, the frustration is less about one missed trophy than about a promising young group that did enough to get noticed without quite breaking through. [Read more 🡒]