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Joey Pollizze
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Updated at May 9, 2026, 19:22
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With a depleted rotation threatening their season, Chicago’s front office may go all-in to secure elite arms like Freddy Peralta or Robbie Ray before the summer deadline.

The Chicago Cubs will be looking to add a starting pitcher at August’s trade deadline. 

With the injuries to Cade Horton, Justin Steele, and now Matthew Boyd, there’s a high probability the Cubs will do all they can to land a top starting pitcher. 

The good news is that there could be some high-quality arms available for trade this summer. Most of the expected available pitchers are likely to be on the last year of their deal and on non-contending teams. 

So, let’s take an early look at three pitchers the Cubs could target at the trade deadline. 

Freddy Peralta 

We learned on Friday that the Cubs had already spoken with the New York Mets about All-Star pitcher Freddy Peralta. With Peralta in the last year of his deal and the Mets sitting in last place in the National League East, it’s becoming more likely that he could be dealt by August. 

Peralta would be the perfect addition for the North Siders. The Cubs are obviously very familiar with the right-hander from his time with the Milwaukee Brewers, and manager Craig Counsell knows him very well from both of their time in Milwaukee. 

Peralta has easily emerged as one of the top starting pitchers in baseball. He is coming off his best all-around season on the mound in 2025 (2.70 ERA and 204 strikeouts) and is off to another strong start this year. The Mets pitcher currently owns a 3.12 ERA and 43 strikeouts. 

Joe Ryan 

Minnesota Twins starter Joe Ryan has been a part of trade rumors for most of the last year. The Twins aren’t in a spot to win now, and Ryan will turn 30 years old in early June. His name will no doubt pop up in trade rumors again this summer. 

Now, Ryan will not be a free agent after the 2026 season, unlike the other two names on this list. He is under team control through the 2027 campaign, which means the Twins technically don’t need to trade him this year. 

However, Minnesota could still look to move him for a big package. Ryan has been one of the most consistent pitchers in baseball over the past few years and currently has a 3.72 ERA and 40 strikeouts across 38 ⅔ innings pitched this season. 

Robbie Ray 

It would be a surprise if the San Francisco Giants do not move Robbie Ray at the trade deadline. San Francisco currently sits eight games under .500 at this point in the season (15-23), and Ray is in the final year of his deal with the team.  

Unless the Giants go on a nice run from now until July and get back into the playoff picture, they are looking like prime sellers at August’s trade deadline. That would make Ray an expendable piece as San Francisco looks ahead to 2027. 

Ray should absolutely be on the Cubs' radar if the Giants do plan to sell him. He was an All-Star last year and has a 2.76 ERA and 47 strikeouts across 45 ⅔ innings pitched this season.