Why Pirates might regret not trading Paul Skenes to Yankees last season

The Pittsburgh Pirates are having a very promising 2026 season, as they've been one of the better teams in the National League, and they currently reside in a Wild Card spot.

With how good the Pirates are this season, the struggles of Paul Skenes have been a bit of a surprise. After back-to-back seasons with an ERA below 2.00, he's struggled a bit, posting a still great, but not Cy Young caliber, 3.09 ERA this season.

But, this minor regression from Skenes had one fan ask Chad Jennings of The Athletic a "What-if" question about Skenes, and more specifically, if they regret not trading him to the Yankees last season.

Why Pirates might regret not trading Paul Skenes to Yankees last year

The reason why this fan asked this question is thanks to the report from Jon Heyman of The New York Post, which indicated that the Yankees "were prepared to offer four top prospects last July" to acquire Skenes from the Pirates.

"The prospects involved were not identified," Jennings writes, "but the report did note that Cam Schlittler, Spencer Jones, George Lombard Jr., and Carlos Lagrange might have been the best prospect package the Yankees could have put together at that time."

There is no guarantee that those were the four prospects that the Yankees were offering to the Pirates for Skenes. But, assuming for a second that those four did make up the Yankees' offer, it's hard not to see how the Pirates might've been better off taking that deal.

Schlittler has a 1.89 ERA with a 7-3 record and 84 strikeouts across his 13 starts during the 2026 season for the Yankees. He's firmly in the Cy Young conversation this year.

Skenes has a 3.09 ERA with a 6-5 record, and is well outside of the Cy Young talk in the stacked NL field this season.

Spencer Jones is a fun prospect who would be an instant upgrade over Marcell Ozuna at the designated hitter spot, or in the outfield as a power hitter with a high strikeout rate like Oneil Cruz.

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Add in Lagrange, who is a flame-throwing pitcher who could be a high-upside reliever or a quality starting pitcher, and Lombard Jr., who could be contending for a big league roster spot at third base for the Pirates right now if this trade were made.

There's no telling if Schlittler would've been this good for the Pirates as he has been for the Yankees, or whether this was the actual offer the Yankees were prepared to make.

But, as Jennings noted, "Can't blame Pirates fans, especially those who assume Skenes is going to leave eventually, for actually finding a Skenes trade they might have liked."

While the Pirates might regret passing on such a great offer for Skenes, especially if the rumors of Skenes' departure in the near future were to come true.

But players like Skenes don't grow on trees, and even though the package would've been a fun one for the Pirates, there isn't anything wrong with keeping Skenes for as long as possible, even if it means he simply leaves in free agency in a few more years.

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