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Chicago Cubs fans have been put through the wringer since this past trade deadline.
Of course, the team's up-and-down play that led to an unceremonious Wild Card exit has a lot to do with that. But the Cubs have also been in and out of conversations surrounding one of the best pure talents in the league.
Tarik Skubal was finally dangled in the trade market during the 2026 season. Chicago was rumored to be among the interested teams, only for the Los Angeles Dodgers to predictably come in and acquire the ace. Nevertheless, with his free agency looming, the Cubs remained tied to Skubal amid their obvious rotational needs.
Did it ever feel like the Cubs should be considered the frontrunners for Skubal? No, but Jed Hoyer's recent aggressiveness had some believing Chicago could remain in the mix as free agency heated up. Alas, a storm cloud of cold water arrived on Monday morning.
According to The Athletic's Sahadev Sharma, the Cubs are prepared to sit out the Skubal market. With plenty of the league's top spenders expected to throw their hat in the ring, Hoyer plans to turn his attention elsewhere to fill multiple roster holes.
The news is bound to frustrate some. Chicago has repeatedly refused to match the spending prowess of teams like the Yankees, Mets, Dodgers, and even Padres in recent years, despite serving as one of the elite major market franchises. We also know that many of the game's top players are drawn to the team. In other words, convincing them to put pen to paper likely wouldn't be all that difficult as long as the money is right.
At the same time, if the Milwaukee Brewers and Tampa Bay Rays proved anything, it's that depth matters far more than superstardom. Both teams have their fair share of All-Star-caliber players, to be clear. But those organizations have focused far more on ensuring they have a well-rounded roster. You can't necessarily blame Hoyer for wanting to do the same.
Indeed, the Cubs don't just have one spot to fill on the mound. This is a win-now team that needs to essentially reinvent its entire starting rotation. Add in two openings in the outfield corners, and the Cubs can't afford to put all their eggs in one basket.
With Tarik Skubal all but off the priority list, The Athletic suggests that the Chicago Cubs could look to bring in three new starting arms.
Sahadev Sharma throws out a long list of interesting names, many of which we've discussed in recent weeks: Michael King, Freddy Peralta, Adrian Morejon, and overseas sensation Kaima Taira. The former would be arguably the most exciting splash for the Cubs, as he might as well be the second-best available player this offseason. However, there are also concerns about his price tag soaring too high.
For what it's worth, it feels unlikely that the Cubs sign more than one of those four big-name targets. What's far more plausible is that they do pay up slightly to sign one before pivoting to a lower tier of starters. Other names that stand out as more cost-effective short-term options are Tyler Mahle, Trevor Rogers, Robbie Ray, and Nick Pivetta.
There is also a good chance that we will see the Cubs decide to re-sign one or two of their own free agents. Clay Holmes feels No. 1 on this list, and Sharma essentially confirms as much. There is a reason why Jed Hoyer gave up as much as he did to bring him in this deadline. Holmes just fits with what this Cubs team likes to do, and the fact that he also has plenty of bullpen experience sure doesn't hurt! That versatility makes you feel even better about how he could age moving forward.
David Peterson feels like the other name to keep an eye on. He had a fantastic season for Chicago after coming over early in the year from New York. Is there some overlap between what he and Holmes provide? Sure, but that hasn't stopped the Cubs before!
Anyhow, the main takeaway seems to be that the Cubs have no plans to make a giant free agent splash this offseason. Perhaps we'll see something a little more exciting in the trade market, but it currently feels as though Hoyer will keep his sights set on balancing out the roster for (hopefully) a healthier 2027.