Cubs' Tarik Skubal retreat acknowledges overhaul required to compete with Brewers

Over the last four seasons, the Milwaukee Brewers have proved time and time again that they are a tier above their arch rivals, the Chicago Cubs. From winning four straight division titles (and five of the last six) to defeating the Cubs in the 2025 NLDS to knocking off the San Diego Padres in this year's NLDS after they embarrassed the Cubs in the Wild Card Series, the Brewers have made clear the obvious gap that exists between them and their I-94 rivals.

The future outlook of both organizations paints an even brighter picture for the Brewers. While Milwaukee celebrates their World Series win and anticipates a largely unchanged roster returning for the 2027 campaign, the Cubs are on the cusp of a roster overhaul that puts pressure on their front office's performance before MLB's lockout begins on December 1. Not only do the Cubs have to worry about replacing or re-signing Ian Happ and Seiya Suzuki to fill their corner outfield positions, but Chicago's starting rotation is in need of a complete overhaul.

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 officially hit free agency, leaving Jed Hoyer and Chicago's front office with plenty of work to do over the next three weeks. The big-market Cubs certainly have the money to replenish their starting rotation, but with so many innings to fill, not to mention their corner outfield dilemma, Chicago can't afford to throw all of their eggs into one basket.

Therefore, Sahadev Sharma's report for The Athletic this morning is perhaps unsurprising. Sharma reported that the Cubs, who were previously thought to be legitimate players in the Tarik Skubal sweepstakes, "appear unlikely to enter the bidding war for two-time Cy Young Award winner." With a need to fill more innings than one pitcher, albeit one of the best pitchers in the game, can fill, the Cubs can't afford to give Skubal the contract he will command. Perhaps if the gap between the Cubs and Brewers were closer, and could be closed by adding one superstar pitcher to the top of their rotation, Chicago's assessment of the Skubal sweepstakes would look a little different.

Cubs' required offseason rotation overhaul won't allow them to be serious players for Tarik Skubal

If the Cubs were one arm away from dethroning the Brewers in the NL Central, fans would undoubtedly see Hoyer and company make a stronger push for Skubal. However, as both rosters currently stand, the Cubs aren't one arm away from challenging the Brewers for the division crown. Heck, the Cubs aren't one arm away from having a complete five-man rotation on Opening Day next year. Chicago needs to add at least two arms, if not three, to their rotation this offseason as well as a corner outfielder, and signing Skubal wouldn't allow them to do so.

Thus, the pressure is on the Cubs' front office to piece together a playoff-caliber rotation from what is a rather weak free agent class. Certainly, the Cubs could seek out reunions with Gausman or Holmes and strong options like Freddy Peralta, Trevor Rogers, and Michael King exist on the free agent market, but signing anyone of those arms and Skubal, while also finding a solution to their suddenly-thin outfield group, feels impossible.

The overarching point for Brewers fans here is that while conversations about how the Cubs will replace their 2026 rotation in 2027 currently dominate the headlines, what isn't being talked about is how Chicago plans to close the 14-win gap that existed between them and the Brewers this year. In other words, the Cubs begin the offseason wondering how they will replace the production they are losing to free agency, not how they can improve on last year's squad to compete with the Brewers for a division title in 2027.

It's an admirable spot to be for the Brewers, whose lack of organizational needs this offseason are the result of their front office's forward-thinking approach to roster construction and the clubs' investments into player development. While other teams are scrambling to replace departing talent, the Brewers, fresh off of a World Series title, are simply waiting for their players to reach their full potential.

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