Projecting Pirates’ Extension for Paul Skenes
In this story:
After signing top prospect Konnor Griffin to a nine-year, $140 million extension, the Pittsburgh Pirates' next order of business is sorting out Paul Skenes' future.
The former No. 1 overall pick and reigning National League Cy Young Award winner is under club control through the 2029 season, meaning there's still ample time on both sides, but there also has to be some urgency on the Pirates' side for a multitude of reasons.
Paying an exorbitant amount of money to a pitcher is always a riskier proposition than doing so with a position player, but Skenes is an exception.
The true willingness of either party to engage in conversations surrounding a long-term deal is unknown, but there are a number of different examples from around the league that they can draw upon as a starting point.
Best Comparisons
The most recent, and perhaps all-around best short-term, comparison for Skenes is Boston Red Sox ace Garrett Crochet.
After being dealt to the Red Sox from the Chicago White Sox ahead of the 2025 campaign, Crochet agreed to a six-year, $170 million extension. He proceeded to finish second in AL Cy Young Award voting with a league-best 255 strikeouts and 2.59 ERA in 205 1/3 innings.
Jacob deGrom agreed to a five-year, $137.5 million extension with the New York Mets fresh off his 2018 NL Cy Young Award-winning campaign, serving as another solid example in this case.
The caveat, though, is that both had two years of club control left when they signed their new deals, whereas Skenes has four, including the current season, meaning he has more arbitration years that have to be bought out.
The largest pitcher contract of all-time belongs to Yoshinobu Yamamoto at 12 years and $325, which he agreed to with the Los Angeles Dodgers after coming over from Nippon Professional Baseball in Japan.
Skenes would have no issues topping that amount if he's seeking out a long-term extension with the Pirates, but Tarik Skubal is the true watermark for the former's market.
The back-to-back AL Cy Young Award winner is in the final year of arbitration with the Detroit Tigers, meaning he'll reach the open market this upcoming offseason.
Since Skubal will likely break the $400 million mark, Skenes would then look to best whatever the former makes as a means of resetting the market.
What Would a Skenes Extension Actually Look Like?
Skenes would have no issues topping Yamamoto's amount if he's seeking out a long-term extension with the Pirates, but Tarik Skubal is the true watermark for the former's market.
The back-to-back AL Cy Young Award winner is in the final year of arbitration with the Detroit Tigers, meaning he'll reach the open market this upcoming offseason.
Since Skubal will likely break the $400 million mark, Skenes would then look to best whatever the former makes as a means of resetting the market.
In a scenario where Skenes is only tenable to a short-term deal that buys out his remaining years of control and perhaps one season of free agency, it make take a pact in the neighborhood of four years and $130 - $140 million.
As for a long-term contract that would keep him in Pittsburgh for over a decade, though, it's not far-fetched to suggest that the 23-year-old could be looking for up to $500 million, which might be far too pricey for the Pirates.
For that reason, Pittsburgh's focus would likely be on a shorter-term extension that delays his free agency by a year or two, while Skenes has his sights set on resetting the market, as previously mentioned.
An agreement between the two parties certainly isn't imminent by any means, but the situation bears watching moving forward.
Jack is a New Jersey native who graduated from the University of Pittsburgh as a Media & Professional Communications major in 2024 who is now covering the Pittsburgh Steelers and New York Yankees for On SI.