How well the Cubs pitching staff has performed through this point of the season is nothing short of remarkable considering all of their injury problems. Their young star Cade Horton is out for the season after having elbow surgery, and Justin Steele, who was out almost the entirety of the 2025 season, suffered a setback in his elbow injury, leaving him sidelined until at least the All-Star break. By the time he's back, it will have been nearly 18 months since Steele last pitched in an MLB game, and it's no guarantee he will resume his prior dominance. On top of these injuries, Matthew Boyd has had multiple stints on the IL through barely 1 month of baseball.
Despite the starting rotation being decimated by injuries, guys have stepped up and found ways to have good outings for Chicago. Namely, Colin Rea and Jameson Taillon have stepped up big time alongside Shota Imanaga and Edward Cabrera who have both had excellent starts to the season. Those 4 guys alongside a healthy Matthew Boyd is a feasible regular season rotation, but it just won't cut it come playoff time. Chicago needs to make a splash move for an elite starting pitcher by the deadline, and 3 guys specifically fit this bill perfectly.
Joe Ryan
The Minnesota Twins are just simply a bad baseball team, meaning that Ryan, who is a free agent after the 2027 season, should be available for the right price. A few of the things Ryan specializes in are things that the current Cubs pitching staff sometimes struggles with: Striking a lot of guys out, and limiting the long ball. He's been Minnesota's ace for several years now, and the Cubs should most certainly be making calls as the trade deadline comes closer. A package including Matt Shaw and some prospects may be hard for Minnesota to resist given the fact that Ryan could walk away after next season for nothing.
Logan Webb
Webb has been the fan-favorite trade candidate for Cubs fans as of late after the San Francisco Giants traded away catcher Patrick Bailey to the Cleveland Guardians for prospects. It's easy to see why: The Giants ace has been nothing short of consistently elite over the years, and San Francisco may finally be realizing that their team just isn't built to compete at the moment. In the case that they go for a full rebuild, Webb will likely be dealt away, and Chicago is the perfect destination for Webb to finally find playoff success.
Freddy Peralta
Peralta feels like the best-case scenario out of these three guys for a couple reasons. The first is that he's a free agent following this season, meaning the New York Mets' asking price can't be absurd, considering Peralta may very well be just a rental. There are a few reasons however as to why Peralta may not just be a rental for Chicago. He shared time with manager Craig Counsell in Milwaukee, and the Cubs most certainly have the money to offer him an extension after this season. Even if there's a chance that he would be a rental for one playoff run, he has playoff experience and stuff that misses bats, two things the Chicago rotation is in dire need of.
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