The Pittsburgh Pirates rank 28th in the MLB in 2025 salary cash totals according to Spotrac, but are they willing to change that business model someday in order to retain superstar starting pitcher Paul Skenes?
Skenes, 22, has quickly cemented himself as one of baseball's most dominant aces. Through 30 career starts, he maintains an ERA of 2.15, with a filthy strikeouts per nine innings of 10.8 and a WHIP of 0.939.
Although the 6-foot-6 starter's numbers have taken a slight dip so far in 2025, it's very apparent that there are few pitchers with the talent and trajectory of Skenes in all of baseball.
And for that reason, he is expected to earn a historic contract.
On the morning of May 6, ESPN MLB insider Jeff Passan predicted some of the biggest contract extensions that are looming around the league, whether in 2025-26 or future offseasons.
"If it's not [Tarik] Skubal (or [Eury] Pérez), it's bound to be Skenes [that sets the new record for the largest contract ever awarded to a pitcher]," Passan noted.
"The 22-year-old helped his clock by winning Rookie of the Year and the full year of service that comes with it," the insider explained. "He'll be just 27 when he's on the market after the 2029 season. And if Skubal (or Pérez) does indeed crack the $400 million threshold, it would be no surprise to see Skenes -- the best pitching prospect in a generation -- parlay his productivity, age and marketability into becoming baseball's first half-billion-dollar pitcher."
Despite that $500 million teaser, Passan predicted that Skenes will end up in the $400 million-plus range when he eventually gets his payday, just above the Detroit Tigers' Cy Young winner, Skubal.
If the Pirates are interested in paying an amount like that, they'll have to not only pony up the cash but convince Skenes that it's worth it for him to play out the majority of his career in Pittsburgh.
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