The New York Yankees are known for making big swings in the trade market, and 2025 was no exception. Despite being in desperate need of relief pitchers and a solid third baseman, they tried to land Pittsburgh Pirates’ flame-throwing right handed pitcher Paul Skenes. The Yankees reportedly offered up top prospects George Lombard Jr. (shortstop) and Spencer Jones (outfielder) for Skenes.

That trade would have been a huge mistake for the Yankees.

While adding Skenes would be a huge boost for any team, including the Yankees, it simply doesn’t make sense for a team who already has what it takes to win. New York’s starting rotation was struggling in the middle of the season, feeling the loss of Gerrit Cole and Clarke Schmidt, who both had to undergo Tommy John surgery, acutely. However, with the emergence of rookie pitcher Cam Schlittler, the Yankees appear back on track and solidly in the AL Wild Card.

Plus, the Yankees were better able to cash in their trade capital to secure immediate needs, including new relief pitchers (though, admittedly, the Yankees bullpen has been leaving little to be desired lately) and a solid fielder at third base in Ryan McMahon.

Sep 4, 2025; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates starting pitcher Paul Skenes (30) delivers a pitch against the Los Angeles Dodgers during the first inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images / Charles LeClaire-Imagn Images

Skenes is an incredible player, but the Yankees run too many risks with dealing away their top prospects, especially for a team that is consistently competitive and won’t have the benefit of another top draft pick like the Pirates do. The Pinstripes’ biggest problems in 2025 are an inability to get runners on base and sloppy defense, not the absence of strong starting pitchers. Players like Lombard Jr. and Jones are too valuable to the Yankees’ future to deal away to solve a problem that isn’t very immediate, especially since Cole and Schmidt will be available for next season.

However, Skenes is under contract with the Pirates until after the 2029 season. It seems equally likely that the Pirates, an organization known to deal talent to their fans’ chagrin, trade him now or keep him through those years. Should the latter occur, the Yankees could be one of the top teams targeting Skenes, simply because they don’t retain prospects for long.

While the Yankees would certainly benefit from adding Skenes to the rotation, and New York fans would certainly love to see the phenom decked out in Pinstripes, making a play for him any time before 2027 would be foolish if it involves sending top prospects away. To make it back to the World Series in the near future, the Yankees should focus on solidifying their home-grown talent, not being perennial buyers at the trade deadline.

Make sure to bookmark Yankees On SI to get all your daily New York Yankees news, interviews, breakdowns and more!