How Risky Will Cubs be at the Trade Deadline? We Might Have an Answer

The Chicago Cubs are going to add a starting pitcher at the 2026 MLB trade deadline.

While this could be assumed after taking a glance at the organization's IL, it's also been the crux of every report this past week. This has been the case despite performing like one of the best teams in baseball over the last month. They may remain 6.0 games back of the Milwaukee Brewers for the divisional lead, but they are well-positioned to lock in a top Wild Card spot and possibly go on an October run.

Nevertheless, a trip to the World Series would feel nearly impossible without upgrades to their rotation. Not only do contributors like Edward Carbera and Ben Brown remain injured, but the starting group as a whole has underwhelmed. The Cubs need to find themselves an ace to round things out, and this deadline is equipped with a long list of impressive names.

Tarik Skubal and Joe Ryan represent two of the best names that could be on the move. The Cubs have been connected to both at times this year, and there is still reason to believe they could swing for the fences in the lead-up to the deadline. At the same time, acquiring either would be a risk when considering the asking price and contract situation. And that risk might be too big for Jed Hoyer to take.

A new report from ESPN's Jesse Rogers clarified just how aggressive the Cubs plan to be in the coming days. While the franchise sounds ready to part with some top prospects, it will be hesitant to do so for an arm that can't help them past this October.

"Like a lot of teams, the Cubs are looking to add a starter and are willing to part with a higher-ranked prospect for a pitcher under team control for several more years. Otherwise, they'll go the rental route with a lower-ranked prospect. In other words, this won't be like 2016 when they traded their No.1 prospect (Gleyber Torres) for two months of Aroldis Chapman," Jesse Rogers wrote.

Cubs Trying to Mitigate Risk at Trade Deadline

May 26, 2026; Pittsburgh, Pennsylvania, USA; Chicago Cubs right fielder Seiya Suzuki (left) and Cubs president of baseball operations Jed Hoyer (right) talk at the batting cage before the game against the Pittsburgh Pirates at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

All things considered, this latest report may not be shocking, but it certainly is informative.

No team wants to give up their best prospects for a short-term rental. However, this is undoubtedly what many organizations do when they are in contention mode. And the Cubs fall into that category. As up and down as this 2026 campaign has been for them, their highs have been as high as any team in baseball. Once again, these past six weeks have been electrifying, as they have surged back up the league power rankings with their offensive explosion and elite defense.

If a team does end up grabbing Tarik Skubal or Joe Ryan, they will be dumping some of their best young players. So, what do Jesse Rogers' words tell us? That we can almost fully shut the door on the Cubs targeting either arm. We may even be able to rule out the Mets' Clay Holmes and the Blue Jays' Kevin Gausman. Both have gained real steam in recent weeks and thus could force a team into giving up a top prospect or two.

Freddy Peralta may be the biggest-name rental who wouldn't force the Cubs to give up one of their favorite guys. To be sure, we wouldn't have said this in the offseason, but Peralta has struggled pretty heavily in his first season with New York. His 5.01 ERA has left a lot to be desired, and the Cubs would essentially be banking on Craig Counsell's ability to fix his old ace.

Robbie Ray feels like another piece who could make a lot of sense. He's put together a really strong year and has only looked better as of late. However, Rogers recently reported that he doesn't expect the return for San Francisco to be all that significant.

Regardless, the far more important names to keep an eye on moving forward are those who are cost-controlled. The Angels' Reid Detmers has been a very popular player attached to Chicago and now feels even more like a top target. The same could possibly be said about his teammate, José Soriano.

Sandy Alcantara has repeatedly been tied to the Cubs over the years, but whether the Marlins truly plan to put him on the market remains to be seen. The Giants' Logan Webb and the Royals' Michael Wacha have come up plenty in recent weeks and would both bring All-Star-caliber production to the staff and warrant a significant return.

Again, it's not necessarily shocking to hear that the Cubs want to be picky about how they deal their top prospects. But it does give us an idea of just how aggressive they plan to be. Will they be more aggressive than a season ago? Absolutely. But they seemingly aren't prepared to push every last one of their chips in for a World Series run.

Could that be a mistake with how well they've been playing? It's possible. The idea of landing Tarik Skubal and re-signing him is also pretty darn tantalizing. Nonetheless, it's hard to blame Chicago for being a little risk-averse. Selling the farm is never an easy choice and can certainly backfire.

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