1 buy-low, 1 realistic, and 1 dream Cubs 2026 trade deadline target for ailing starting rotation

The Chicago Cubs have been forced to mix-and-match pieces for their starting rotation since the first week of April, and the calendar now provides a real sense that help is on the way. Jameson Taillon should be reinstated from the IL as soon as this weekend, and the MLB trade deadline is now within sight.

Now, yes, the Cubs were in a similar position last summer. There was a clear need in the starting rotation, and the front office waked away with an oft-injured Michael Soroka as the only potential solution for the rotation. That can't be the the case this time around.

For one, there's no Cade Horton helping the rotation during the closing months of the regular season. Beyond that, even if Justin Steele and Ben Brown return this season, it will likely be to roles in the bullpen. Edward Cabrera should be back in the rotation before September, but nothing about his 2026 season would suggest he's going to be an immediate answer for what the Cubs need in the rotation.

The Cubs need rotation help at the 2026 MLB trade deadline, but how will they accomplish that?

The Cubs adding a starting pitcher before the trade deadline is not the question. They have to. The question is just how aggressive will Jed Hoyer and Co. be as they do so.

Clay Holmes is an ideal buy-low gamble for the Cubs at the deadline.

In a world where the Cubs look to add two starting pitchers to the rotation before the deadline, Clay Holmes of the New York Mets would be a worthwhile gamble. Holmes has been sidelined since May with a fractured fibula, but he has resumed his throwing program and prepping for a return in the coming weeks.

Holmes has a player option for the 2027 season, and given the injury, there's a chance that he avoids free agency this offseason. Especially since there'll likely be a work stoppage and stunted free-agent market. If the Mets make him available, the Cubs should be involved. Holmes is the type of pitcher the Cubs have, having an ERA of 2.39 this season with a ground-ball rate of 56%.

Robbie Ray is a realistic trade deadline target for the Cubs, but there would be questions.

There are several pitchers who fit into the "realistic" category for the Cubs. And, chances are, this is the bucket that the Cubs' deadline addition will be in. One name that continues to stand out above the rest is Robbie Ray.

Ray is a pitcher the Cubs have liked for a few years, and the San Francisco Giants are clearly going to be sellers this summer. If nothing else, Ray is an innings eater capable of taking the ball every five days, and he sports a 3.38 ERA in tick under 107 innings pitched this season. The problem is that his ERA may be smoke and mirrors, sitting with an FIP of 4.70 and walking over 11% of the hitters he faced.

Logan Webb is a dream target for the Cubs, but the Giants would need to be overwhelmed

It's easy to say Tarik Skubal here, but it's also easy to understand why the Cubs won't be the team to make that trade. Plus, the Tigers are making up ground in the American League Central. Joe Ryan is also an obvious choice, but the Twins are also "contenders" this season, and the placing value on his control next season could be complicated.

The true dream target, like Ray, is also with the Giants. Logan Webb is under control through the 2028 season, and would be the clear ace of the Cubs' rotation moving forward. The problem, beyond wondering if Jed Hoyer would be comfortable with the asking price, is that the Giants don't have any intention of moving Webb. At the very least, the Giants would need to be overwhelmed and that is probably where the Cubs are removed from the conversation.

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