With a need for pitching, the Chicago Cubs can't really ignore any option that is available this offseason. While the impression has been that the Cubs won't really be involved in the bidding for Tarik Skubal this winter, The Athletic's Patrick Mooney set the stage for the Cubs potentially being involved at the surface level.
The latest episode of the North Side Territory took a look at free agents who make sense for the Cubs this offseason, and there's an important distinction that it leans more toward speculation than it does sourced reporting. Along those lines, Mooney talked about the Cubs and Skubal, suggesting that idea may not be far-fetched, considering the circumstances involved.
Tarik Skubal to Chicago isn't as far-fetched as it sounds. 💰
— North Side Territory (@NSideTerritory) October 13, 2026
The Cubs have the money, the need, and some intriguing connections to the ace. @PJ_Mooney explains why they shouldn't be counted out. pic.twitter.com/vZaFUnLb8M
Cubs' seemingly impossible Tarik Skubal pursuit gets unexpected life from insider
Skubal spends his offseason in Arizona, which could be viewed as a benefit to the Cubs, considering that is where their spring training facility is. The Cubs did their due diligence on Skubal at the deadline, and it would seem that the impression from the front office is that he passed all of their checks. Again, that is somewhat obvious, considering Skubal has been one of the best pitchers in baseball over the last few years.
As the Cubs insiders stressed, the team shouldn't be viewed as the favorites for Skubal. That is likely going to toss-up between the Los Angeles Dodgers and New York Mets. In a world where the Dodgers do their version of a reset and the Mets opt against spending top dollar this offseason, perhaps the path to the Cubs would be clear.
On paper, Skubal and the Cubs are a clear fit. That's more or less what this messaging confirms. It would seem that at the GM meetings next month, there will be a clearer sense of the lane the Cubs are shopping in. Even with a lockout looming on December 2, the expectation is that November will be a busy month, and MLB is moving forward with the annual front office meetings.
This feels like the usual October script for the Skubal. Educated speculation that suggests the Cubs should be involved with the names at the top of the free-agent market, and then reality settles in once the market begins to move. Perhaps there's a surprise for the Cubs that includes Skubal, but past history would suggest that fans shouldn't hold their breath.
