The idea of Tarik Skubal sporting a Chicago Cubs jersey has largely felt like a dream.

Yes, the franchise has been named a suitor multiple times in the past. This included at the recent MLB trade deadline, when he was ultimately traded to the (*sarcastic gasp*) Los Angeles Dodgers. For as obvious as the Cubs' pitching needs are – let alone their win-now intentions – it just hasn't felt as if they would be willing to pay what it takes to keep Skubal in Chicago long term. Handing out those kinds of monster deals just hasn't been their MO.

Nevertheless, the Cubs have continued to loom in the Skubal conversation, which will likely stretch deep into the offseason as he sits as the best available player. Does it feel like the Dodgers are most likely to retain the lefty? Sure, but ESPN's Jeff Passan suggested in a recent report that the Cubs still have him circled as an offseason target.

"The two most obvious suitors are the two teams with the highest payrolls in baseball: The Los Angeles Dodgers and New York Mets. There are bound to be others," Passan wrote. "The Chicago Cubs badly want Skubal. They also are skeptical that they will be willing to compete at the sort of dollars Skubal is expected to get -- well in excess of $300 million, potentially in the $400 million-plus range. With Michael King and Nick Pivetta being free agents, the San Diego Padres need a rotation anchor, and arguably the best pitcher in baseball would more than suffice."

It may not be the kind of report that sounds alarms around Wrigley Field, but it's enough to perk up the ears!

Cubs Want Tarik Skubal "Badly"

Obviously, there is a major difference between wanting something and making it happen. Heck, I'd love a penthouse suite with floor-to-ceiling windows and a robot butler that makes superb meatball sandwiches. Will I ever acquire that? It's unlikely, especially if I'm not willing to pay up!

As Passan states, there is still clearly a belief that the Cubs will not be willing to pay the price necessary to bring in Skubal. And, again, that is very on-brand for the organization as a whole. But this is also a franchise that has gradually been more aggressive over the last-year plus, starting with the five-year, $175 million signing of Alex Bregman.

Chicago is pretty clearly in a win-now window and believes it has a shot at a World Series run. Look no further than their trade deadline, when they added multiple high-profile players for a (failed) postseason sprint. They will also head into this offseason with tons of money to spend and a glaring hole at the top of the starting rotation. If there were an offseason to finally push all your chips in, this might very well be the one.

Is it far more likely that the Cubs target an arm that ranks a tier below? Probably, and Michael King might fit the bill. However, the smoke has lingered long enough around Chicago and Skubal that there might actually be a fire. You'd have to imagine that they could make him a pretty convincing pitch. While they fell short in 2026, they were still among the elite two-way teams in baseball with a true superstar in Pete Crow-Armstrong. Solve the rotation struggles, and the Cubs will be viewed as a true World Series threat.

None of this is to say that Cubs fans should get their hopes up just yet. They are not considered the favorite to land Skubal for a reason. At the same time, Jed Hoyer has displayed a willingness to change his team-building approach over the last year, and the ultimate next move would be to secure the best pitcher in baseball.