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MLB insider lists 3 trade deadline options for the Chicago Cubs

Chicago sure looks like a World Series contender, meaning there's no better time for Jed Hoyer to go all in.
New York Mets v Colorado Rockies
New York Mets v Colorado Rockies | Dustin Bradford/GettyImages

Key Points

Bullet point summary by AI

  • The Chicago Cubs, leading the NL Central at 27-14, face pivotal trade deadline decisions to bolster their postseason push.
  • Potential moves include adding a frontline starter to shore up a rotation depleted by injuries to key pitchers.
  • One realistic path involves targeting a high-impact arm, with several compelling options emerging as the deadline approaches.

The Chicago Cubs identified an opportunity this winter and were aggressive in bolstering their roster. They signed Alex Bregman. They traded for Edward Cabrera. They kept Shota Imanaga. And they bolstered the bullpen with four additions, while reaching an agreement with the injured Shelby Miller with an eye on the future.

It’s been a massive success, with the Cubs at 27-14 and in first place in the National League Central. They have the second-best record in the NL, ahead of the Dodgers and only one game behind the Braves, and appear to be a team primed for a deep postseason run.

And Jed Hoyer, the Cubs’ president of baseball operations, should go for it at the deadline.

There’s a few ways that the Cubs can go about improving this roster for the stretch run. They could acquire another bat to bolster a lineup that already ranks third in runs scored (215). They could bolster an injury-plagued rotation that is without Justin Steele, Cade Horton and Matthew Boyd. They could even do both and really go all-in on the 2026 season.

What feels more likely is making a meaningful rotation addition. After losing so many starters to injury, the organization wanted to give the internal options a chance to establish themselves. But in a season that has World Series aspirations, Hoyer and the front office should take a big swing and add a frontline starter.

Let’s dive into a few potential options.

Robbie Ray, San Francisco Giants

Robbie Ray
Pittsburgh Pirates v San Francisco Giants | Andy Kuno/San Francisco Giants/GettyImages

At this point, I consider it likely that Ray is traded. But the Giants do not want to move Ray or any other player at this point; they want to fight to get back into the postseason conversation, and that means holding onto Ray, Rafael Devers, Matt Chapman and Willy Adames. Trading any of those players is off limits at the moment.

But Ray, who is on an expiring contract, is a much more realistic trade option should the Giants continue to struggle. Ray, 34, is one of the top left-handed arms in baseball and has posted a 2.76 ERA in eight starts in San Francisco this season. Durability has been a concern — he pitched in just 11 games from 2023-2024 — but was fully healthy last year and has been healthy once again to start 2026.

Expect to hear plenty of buzz about Ray come July and August.

Joe Ryan, Minnesota Twins

Joe Ryan
Cleveland Guardians v Minnesota Twins | David Berding/GettyImages

This would require a big swing, with plenty of prospect capital going to Minnesota, and I’m skeptical that Hoyer would make a move of this magnitude after trading Owen Caissie to the Miami Marlins for Cabrera.

Ryan, 29, dodged a bullet after a right elbow scare and returned to throw a season-high 107 pitches last week. He’s one of the most dependable right-handed arms in baseball and was a popular target at last season’s deadline, with the Boston Red Sox among teams to show interest. And with a 3.43 ERA in nine starts, he should be popular once again this summer.

But the Twins are trying to build for the future and did not move him during last deadline’s epic sell-off. With Ryan controllable, I’m hesitant to think he’s moved. Still, teams will be calling plenty.

Freddy Peralta, New York Mets

Freddy Peralta
New York Mets v Colorado Rockies | Dustin Bradford/GettyImages

I love this fit. Peralta would be another high-impact pitcher who has National League Central experience, knows Craig Counsell from their time in Milwaukee and is also playoff-tested.

There was a report last week that the Cubs had checked in on Peralta, but that’s not accurate. Chicago has checked in on others, though, and if the Mets continue to slide, Peralta, who is on an expiring contract, becomes an obvious trade candidate. Such a scenario seemed unimaginable entering the season, but the Mets have the second-highest payroll in baseball and yet are the only team currently on pace to lose 100 games. 

It would be a tough pill to swallow, but considering David Stearns’ relationship with Peralta (he’s also traded for him twice), dealing him away at the deadline shouldn’t deter the righty from going back to Queens in free agency.

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