Yankees Took Big Swing at Landing Superstar Pitcher Last Season

Jazz Chisholm Jr. had a great quote about expecting a lot of yourself during the season opener for the New York Yankees. "Why not shoot for the stars and land on the moon," their ever-charismatic second baseman said. It's a type of confidence the organization itself had when it made its first attempt at swinging a trade for a superstar pitcher last year.

That superstar is Paul Skenes. Skenes, who was roughed up in his first game against the New York Mets, thanks to Oneil Cruz struggling in centerfield, was the apple of Brian Cashman's eye at the last trade deadline. He made his first, but probably not last, try to acquire Pittsburgh's star.

According to the New York Post's Jon Heyman, the Yankees were going to offer the Pirates a bevy of young talent. Spoiler alert, it didn't happen.

"Sources say the Yankees were prepared to offer four top prospects last July," Heyman wrote. "It isn't clear who those were, but as of the deadline, their best prospect package might have included some combination of Cam Schlittler (who's now establishing himself as a potential ace), George Lombard Jr., Spencer Jones, and Carlos Lagrange, or possibly others. Schlittler and Ben Rice are the young players most coveted by other teams, and in at least all other instances, the Yankees have been super protective of them."

Mar 15, 2026; Miami, FL, United States; United States pitcher Paul Skenes (30) exits in the fifth inning against the Dominican Republic during a semifinal game of the 2026 World Baseball Classic at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images | Sam Navarro-Imagn Images

Looking to 2030

The closer Skenes gets to free agency, the more the sharks will be surrounding the Pirates, in hopes of taking one of the centerpieces away from them. Who knows how much Skenes will command in free agency, but unless they can figure out a longterm extension akin to what Julio Rodriguez or Pete Crow-Armstrong got, it's fair to assume they may not pay him. It's something they haven't done before, and their fanbase is probably hoping Skenes is the outlier.

This offseason, the Detroit Tigers ace, Tarik Skubal, will command a massive deal. He'll blow past Gerrit Cole's once record pact. Whatever Skubal gets, assuming Skenes keeps his dominant streak going, and Cruz can catch a few more fly balls than he did in game one, Skenes is likely to get even more than that. The winter of 2030 will be a big one for him.

While Hal Steinbrenner doesn't spend as lavishly as his beloved father once did, one thing is clear: if there's a player the Yankees love, they'll unearth every stone to land them. They did it with Cody Bellinger this season, all but announcing to the world that he's their number one target. It was the case with Juan Soto the previous off-season, though there was a Steve Cohen-sized mountain in their way.

Then, with another former Pittsburgh star, they threw the bag at Cole, who is now their ace. In 2030, they might open their wallets in the same way. Attempting to swing a trade may have been one way of showing their affection to the young starter who could be redefining what it means to be an ace.

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