Paul Skenes, future New York Yankee? It’s not as absurd as it sounds

The New York Yankees—not to mention their fans—would love to have Paul Skenes don the pinstripes.

And why wouldn’t they? The Pittsburgh Pirates ace is, hands down, the best thing about the regular basement-dwelling Buccos. Moreover, he just won the NL Cy Young after posting an MLB-best 1.97 ERA on the year. He has a 1.96 career ERA in his first two seasons and was also the NL Rookie of the Year in 2024.

And according to Randy Miller of NJ.com, the idea of Paul Skenes as a Yankee might be more than some social media fantasy. Speaking to one of Skenes’ teammates, who remained anonymous, the big righty has “no confidence” in the Pirates building a winning team around him. Furthermore, word is Skenes wants to be traded before he hits free agency in four years. And even then, the Bronx is heavy on his radar.

“He wants to play for the Yankees,” the teammate repeated. “I’ve heard him say it multiple times.”

In more shocking news, Miller spoke with Pirates general manager Ben Cherington on the matter, and Cherington…didn’t really deny it?

“I do dismiss it, but I understand it,” said Cherington. “What we’re going to focus on is just how do we win games with him in a Pirates uniform. I have a ton of respect for the Yankees, but we’ll just focus on what we need to do.”

Needless to say, Yankees fans are salivating at the idea. Skenes is a special kind of pitcher, featuring a blazing fastball as well as his signature “splinker” which gives hitters fits. Be it as a trade rental a la Juan Soto or signed in free agency like Gerrit Cole, Paul Skenes going to the Yankees would be an objectively blockbuster move.

And knowing Brian Cashman’s front office? Assuming he’s still running the show five years from now, there are several irons in the fire already. He and his team have likely already done both the roster and salary calculus to make sure they can full-blown Godfather Paul Skenes. Make the big righty an offer he just can’t refuse.

Let’s start with the state of the rotation five years down the road. Don’t look now, but Cole and Carlos Rodon are each only signed through 2028. This part is easy because Cole will be 38 by then, and he probably either retires or signs a new, short-term deal to stay in New York. Rodon, on the other hand, will only be 35 and more likely to move on in free agency.

That means as of now, going into the 2029 season—Skenes’ contract year—the Yankees’ rotation looks light. Lefty Max Fried is the only lock and he’ll be 35 on Opening Day that year. Cam Schlittler and Will Warren will be in their arbitration years then, but one or both could be moved in a trade for a bigger name. A bigger name like Paul Skenes, perhaps?

Which brings us to the more interesting aspect of the conversation, which is that the Yankees have a long trade history with the Pirates dating back to the 1970s. Some have helped the Yankees, like acquiring longtime second baseman and coach Willie Randolph in 1975. Others have harmed them, namely shipping budding ace Doug Drabek to the Pirates for the aging Rick Rhoden in 1986.

More recently, however, some of Brian Cashman’s shrewdest deals have been made with the Pirates. The Yankees missed the playoffs in 2008, but Cashman’s trade deadline acquisition that season? Lefty reliever Dámaso Marte, who was instrumental against Chase Utley and Ryan Howard as the Yankees beat the Phillies in the 2009 World Series.

Who helped out Cashman and the Yankees when the Bronx Bombers were desperate to unload AJ Burnett before the 2012 season? That would be the Pittsburgh Pirates.

And how about the double-whammy with two Pirates-Yankees deals in 2021? Cashman traded for righty starter Jameson Taillon in the offseason, then acquired little-known reliever Clay Holmes at the trade deadline.

Taillon was 22-11 with a serviceable 4.08 ERA in two years in pinstripes before signing with the Cubs. Holmes, meanwhile, developed into an All-Star closer and parlayed that success into signing with the Mets last offseason.

Better yet, the Yankees have not “lost” any of Brian Cashman’s deals with the Pirates. None has ever cost the Yankees a serious prospect of consequence, for lack of better word.

Brian Cashman knows the Pirates’ game too well at this point, whether it’s Ben Cherington or the Pirate Parrot running the front office. Pittsburgh rarely ever plays their best players, especially their pitchers. Them trading Skenes is little more than a salary dump whether he’s traded this offseason or not at all.

One thing is certain: Don’t discount Randy Miller’s report. Brian Cashman, like him or not, is probably the smartest general manager in baseball. He’s been in his position since 1998 and hasn’t had a losing season once. That’s no accident.

Paul Skenes, allegedly, wants to be a Yankee. We could be wrong but, knowing Brian Cashman? He’s already well aware.