Jon Heyman Believes Cubs Most Likely to Land Tarik Skubal
I’m a little late on this prediction from Jon Heyman and will only be touching on it briefly, but it does feel important if only for the sake of posterity. Even after having a loose body removed from his elbow recently, Tigers ace Tarik Skubal should return in plenty of time to provide an ample showcase ahead of the trade deadline. With his contract expiring after this season and an extension highly unlikely, he’s almost certain to end up in a different uniform.
The procedure the lefty underwent at the hands of famed surgeon Dr. Neal ElAttrache utilized a cutting-edge NanoNeedle, making it minimally invasive and hastening recovery. That’s good for both Skubal and the Tigers, as having him on the shelf for too long could have tanked his value. Of course, arriving at an agreement on what he’s worth as a rental will still take a fair bit of doing.
While many still put the Dodgers at the head of the pack when it comes to having both the willingness and ability to trade for and/or sign whomever they want, Heyman has other thoughts.
“So my No. 1 team to trade for Skubal is the Cubs,” Heyman said. “They’ve lost 10 in a row. We can get to all the Cubs’ issues in a little while, but certainly hitting is their No. 1 issue. But they lost Cade Horton, obviously a No. 1 pitcher, their No. 1 pitcher, and to me, that makes the most sense for a trade with Skubal. I’ve heard their team floating around a bit, not gonna say how much they’ve talked to the Tigers.
“But we do know that the GM of the Tigers, or baseball president I should say, of the Tigers, Scott Harris, used to be with the Cubs, so he certainly knows Jed Hoyer well, knows their system probably better than most. And their system is pretty good, so the Cubs are my No. 1 fit, we shall see, no guarantees here.”
.@JonHeyman‘s top potential landing spot for Tarik Skubal if he’s moved?
The Chicago Cubs ? pic.twitter.com/PtvcDuAMZI
— B/R Walk-Off (@BRWalkoff) May 27, 2026
It’s hard to argue with the anecdotal evidence here, from the Cubs’ desperate need for pitching to their personal ties with Detroit’s front office, but Heyman may have stumbled a little in terms of their system. After opening the 2024 season ranked No. 2 in MLB Pipeline’s rankings, the Cubs were down to 19th at last year’s midseason update. That ranking fell again this preseason, down to No. 23 and trailing all other teams in the division.
The Cubs had only two top-100 prospects back in March, but Moisés Ballesteros (55) has graduated and Jaxon Wiggins hasn’t pitched in a game since April 4 as he continues to work through elbow inflammation. The latest rankings have Wiggins falling to 88, with Jefferson Rojas (83) and Pedro Ramírez (85) just above him. That’s not exactly what I would call a good system, especially when there are only two other pitchers in the organization’s top 30.
It’s hard to see the Cubs and Tigers coming to a mutually beneficial agreement on what could end up being just a two-month rental. While Hoyer does have some players who appear to be a little redundant — either Rojas or Ramírez, along with Jonathon Long, James Triantos, and one of Kane Kepley or Ethan Conrad — he probably lacks the kind of pitching Detroit would want in return. Wiggins’ health might take him out of the equation, and there’s a bit of a drop from him to Kaleb Wing and Dominick Reid.
We also need to keep in mind that this isn’t just a volume play where the Cubs can offer five random prospects like the worst person in your fantasy baseball league. And it’s not like their system has the kind of top-end depth to absorb a big haul anyway. If they were to trade for Skubal, it would be a damn-the-torpedoes move that would only pay off with a World Series win.
Unless, that is, you believe they’ve got a willingness to offer the largest contract in club history to lock Skubal up for another decade or so.
