Yankees insider's offseason plan features massive surprise pitching trade

The New York Yankees’ 2025 season, which featured a run to the ALDS, would be considered a success inside the front office of several Major League Baseball franchises. But for the Yankees and their unparalleled history, anything short of a World Series has come to represent failure.

Accordingly, it’s jarring for the Yankees that they haven’t brought a title to the Bronx since 2009. GM Brian Cashman’s objective for the upcoming offseason thus comes into clear view: do whatever you must do to get this team back to the promised land, even if that means swinging big on a blockbuster trade.

While plenty of teams have already started calling Cashman about potential trades, Cashman should be making his fair share of calls to other clubs in an attempt to bolster New York’s roster. 

Who should the Yankees target? The Athletic’s Chris Kirschner recently put out a comprehensive blueprint for Cashman, which featured a suggestion to go after Kyle Tucker in free agency. There was, however, an even more shocking proposal offered by Kirschner in his treatise.

Yankees urged to trade for either Joe Ryan or Tarik Skubal this winter

Most, if not all, of Kirschner’s visions for the Yankees were defensible, particularly regarding the club’s pitching staff. For instance, Kirschner’s suggestion about turning Luis Gil into a reliever makes some sense.

Kirschner’s map of moves for Cashman was not without fireworks, either. After reviewing what New York’s starting pitching framework is expected to look like in 2026, Kirschner unleashed a haymaker of an idea.

“The Yankees will have four rotation spots locked in at some point next season with Max Fried, Carlos Rodón, Cam Schlittler and Gerrit Cole returning from Tommy John surgery,” Kirschner wrote (subscription required).. “That leaves Gil, Will Warren, top-100 prospect Elmer Rodriguez-Cruz and Clarke Schmidt, when he returns from elbow surgery, competing for one spot. The Yankees also have Lagrange, Chase Hampton, Bryce Cunningham and Ben Hess in the minors.”

“If willing, the Yankees could package some of these pitchers for one top-line starter, like Minnesota’s Joe Ryan or Detroit’s Tarik Skubal,” Kirschner then added. “Since the Tigers were eliminated in the ALDS, there’s already been chatter on whether Skubal could become available in a trade this offseason. If the Tigers know they don’t have the ability to retain him in free agency next offseason, it would make sense to trade him now and maximize the package they receive. Obviously, Detroit should just pay Skubal considering he’s the best pitcher in the sport, but whether they can keep him is an open question.”

Skubal in pinstripes?! The idea sounds well beyond the realm of plausibility, but Kirschner did a noble job of making it sound not impossible.

With the Los Angeles Dodgers having usurped the Yankees as the premier landing spot for superstars in MLB, getting Skubal would do plenty to help the Yanks fight against that narrative and start gaining some ground back on LA.

It goes without saying that a starting rotation of Skubal, Fried, Rodon, Schlittler, and Cole would be absolutely insane on paper. Even adding a pitcher of Joe Ryan’s caliber to the mix instead of Skubal would give New York a historically impressive group of starters, especially since the Red Sox also have documented intered in trading for Ryan.

Does Cashman still have his fastball? Pulling off a deal for Skubal or Ryan would leave little doubt about the answer to that question.