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Pittsburgh Pirates pitcher Paul Skenes 30 returns to the dugout after giving up two runs in the first inning against the Chicago Cubs at PNC Park on Tuesday, September 16, 2025 in Pittsburgh. PUBLICATIONxNOTxINxUSA PIT2025091615 ArchiexCarpenter

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Pittsburgh Pirates pitcher Paul Skenes 30 returns to the dugout after giving up two runs in the first inning against the Chicago Cubs at PNC Park on Tuesday, September 16, 2025 in Pittsburgh. PUBLICATIONxNOTxINxUSA PIT2025091615 ArchiexCarpenter
With free agency right around the corner, the chatter about where Paul Skenes should go next is heating up again. Of course, Skenes isn’t actually hitting free agency as he’s under contract with the Pirates until 2029. But fans and analysts are calling for a trade as frustration grows over the team’s unwillingness to spend. And now the buzz got even louder after Skenes was named one of three finalists for the NL Cy Young Award this year.
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Meanwhile, the Yankees are being warned to make a move if they want to keep up with their fast-improving rivals. Despite their botched move at the trade deadline, the Yankees could face even tougher competition next season. And that might push them to take a serious look at a player like Skenes!
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Well, the Yankees got their traditional rivalry with the Dodgers. They are yet to avenge their 2024 World Series loss. On the other hand, the Yankees have the Blue Jays as their divisional rival, who also made the Dodgers a run for their money in this World Series. So, just when two of the biggest rivals of the Yankees are performing, the Yankees can’t afford to go till the ALDS like this year. However, they need some good names, and we all know how pitchers are key to winning games.
Here comes Paul Skenes! “I guarantee if you make the rotation, Skenes, Freed, Cole, Schlittler, Rodon, you’re winning the freaking World Series.” Pinstripe Territory host Derek Levandowski shared how the Yankees’ starting rotation would look with Paul Skenes in place.
This season, Carlos Rodon was the Yankees’ top arm, posting a solid 2.86 ERA with 203 SOs. But when you stack that up against Paul Skenes, the gap is hard to ignore. Notably, Skenes dominated the NL with a 1.97 ERA and 216 SOs, tying Jesus Luzardo for second in the NL behind Logan Webb’s 224!!!
Hence, numbers like that make it pretty clear why the Yankees could use a guy like Skenes if they want to keep pace with teams like the Blue Jays and Dodgers. But wait, before knowing that even the Yankees would face competition in pursuing Skenes.
More competition for the Yankees in the race to get Paul Skenes
In the race for Paul Skenes, the Yankees are facing competition in the form of the Red Sox, their other divisional rival! “I could see the Red Sox pairing Paul Skenes up with Garrett Crochet and winning five division titles in a row,” Levandowski added.
If you remember, the Red Sox looked sharp early this year, especially with Crochet leading the charge. But their lack of depth behind him ultimately caught up to them. Even though they fell to their rivals, the Yankees, Crochet’s performance was a big bright spot. We still remember his dominance against the Yankees with just one run and 11 SOs over more than seven innings in his first-ever playoff start!
So, to keep that momentum going, the Red Sox are all poised to add another elite starter behind Crochet. And with Alex Bregman hitting free agency, the Red Sox should have the financial room to make a serious offer to the Pirates for Paul Skenes.
Moreover, in terms of prospects, they can definitely compete with the Yankees. According to BoSox Injection’s Daniel Feininger, a potential trade package could include young pitcher Payton Tolle, top prospect Franklin Arias, and a rookie infielder like Marcelo Mayer or Kristian Campbell! Too good for the Pirates to avoid.
So, with all the rivals of the Yankees surging ahead, it’s a do-or-die scene for them. Go for Skenes right now, or don’t manifest the next World Series.
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