The Pirates Should Extend Paul Skenes — How Much Will That Cost?
Paul Skenes won the 2025 National League Cy Young Award unanimously, cementing himself as the best pitcher in the National League, the best right-handed pitcher in baseball, and right up there with Tarik Skubal as one of the best in the game. Unlike Skubal, or Christopher Sánchez, Garrett Crochet, or Hunter Brown, Skenes is just 23 years old and making $875,000 in salary for the 2025 season.
Skenes is clearly one of, if not the, best young talents in the sport, and the Pittsburgh Pirates are incredibly lucky to be getting such elite production for the dollars they’re paying him. This season also confirmed that—after years of Andrew McCutchen and failed attempts with Bryan Reynolds and Ke’Bryan Hayes—Skenes is the face of the franchise and one of the faces of Major League Baseball.
General Manager Ben Cherington and owner Bob Nutting have given long-term extensions to Reynolds and Hayes while bringing back McCutchen, so we’re operating in a world where the Pirates’ front office is willing to spend money. Back in March, The Athletic openly speculated about what an extension could look like, and Cherington has been making the rounds discussing potential spending. So let’s dig into what the numbers could look like if the Pirates were to extend Skenes sometime this offseason or early 2026—and whether it’s actually feasible.
Final Pre-Arb and Arbitration Years
One of the reasons the Pirates should look to extend Skenes—beyond making fans happy and locking up the face of the franchise long term—is his developing arbitration situation. The organization learned with Bryan Reynolds that these negotiations can be tricky, and ultimately long-term extensions through arbitration years make sense for all parties involved.
Skenes is already an incredibly decorated player after just two seasons, with a Rookie of the Year and a Cy Young Award. He won’t hit arbitration until 2027, so his 2026 salary will be set by the Pirates. They could offer him the minimum, matching his 2025 salary, but in this scenario the Pirates need to come to the table with olive branches. In 2014, Mike Trout set the record for a pre-arbitration contract with a $1 million deal in his third season. Let’s say the Pirates give Skenes something closer to $1.25 million to account for inflation and to set the tone for negotiations.
Any extension should aim to buy out Skenes’s arbitration years (2027–29) and as many free-agent years as possible. Letting him walk to free agency would eliminate some offseason chatter but ultimately only heighten trade discussions around the pitcher. But how much would those arbitration years be worth? Historically, it’s difficult to estimate what Skenes would get in Arb-1 because no one has ever been this accomplished this early. Brandon Woodruff and Dallas Keuchel entered Arb-1 with a Cy Young and received $6.5 million and $7.5 million, respectively—but those deals were years ago. Cody Bellinger holds the record for an Arb-1 contract at $11.5 million, supported by a Rookie of the Year and an NL MVP award.
Since Bellinger seems to be the closest comparison point in terms of production, it’s useful to note that his Arb-2 salary was $16.1 million and his Arb-3 salary was $17 million—despite posting only a combined 1.2 bWAR in those two seasons. Any extension for Skenes would be made in good faith that he’ll continue to improve and his salary will grow year over year. This is where we look to the record books for the highest arbitration salaries, which is a list full of stars. Vladimir Guerrero Jr. holds the current record for an Arb-3 salary at $19.9 million, earned because he was a three-time All-Star, Gold Glover, Silver Slugger, and twice finished top-ten in MVP voting. His salary grew from $7.9 million (Arb-1) to $14.9 million (Arb-2) to $19.9 million (Arb-3).
All of these data points show two things:
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Even if the Pirates don’t extend Skenes, his arbitration years are going to be expensive.
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The Athletic initially estimated those three seasons would cost $38 million. Based on the above, the number is probably closer to $41 million, with Skenes almost guaranteed to surpass Keuchel’s Arb-1 record and land closer to a Guerrero-level salary, with slight inflation adjustments.
Free-Agency Years
Now that we have an idea of the arbitration numbers, it’s time to consider free-agency numbers. This is easier to calculate because every year free agents sign deals that set the new market rate. Last offseason’s best pitcher by bWAR, Max Fried, signed an eight-year, $218 million deal for an average annual value (AAV) of $27.25 million. According to Spotrac, the highest annual salaries for starting pitchers (discounting Ohtani, who is in his own category) are Zack Wheeler at $42 million, followed by Jacob deGrom at $37 million and Blake Snell and Gerrit Cole at $36 million.
Based on when Skenes would hit free agency (2030) and his overall talent, he could be looking at $44 million per year—an MLB record. The benefit of an extension is that the contract could be structured similarly to Julio Rodríguez’s, with player/team options and opt-outs based on performance.
Final Contract Number
When looking at massive pre-arbitration deals across MLB history, the idea is that the player sacrifices a bit of best-case future earnings for long-term security. Skenes is represented by ISE Baseball, which negotiated long-term extensions for Miguel Cabrera and Justin Verlander, both with the Tigers. Neither deal offered much of a discount, but both provided strong returns based on the players’ peak years.
If the Pirates are serious, I think the base of a deal for Skenes looks like a five-year, $125 million extension starting in 2027. That buys out Skenes’s three arbitration years at roughly $41 million total and two free-agent years at $42 million per year. Skenes would be 30 when the deal ends and could hit free agency around the same age as most of his peers, giving him a chance at another massive payday.
The reality is there’s very little incentive for Skenes to take that deal. He’s never had serious health issues that might push him to seek early financial security, and unless he really wants to avoid contract talks until he’s 30, the worst-case scenario resembles Bellinger—missing out on some arbitration value but making it back on the open market.
So let’s take that 5/$125 million base and try to sweeten it. Give Skenes $45 million per free-agent year so he breaks the AAV record, moving the contract to five years and $131 million. From there, you’d need to offer player options or opt-outs tied to performance:
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Multiple Cy Youngs: $50 million AAV for 5–8 years at the end of the deal
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Single Cy Young or MVP Award: $45 million AAV for 5–8 years at the end of the deal
This would make the contract theoretically a 13-year, $531 million mega-deal—one of the richest in baseball history outside of Ohtani.
Could and Would the Pirates Offer This?
The gut feeling across the industry is “no,” based on the Pirates’ history. But the Pirates do have cash to spend and more young players than ever to fill roster spots previously occupied by free agents.
The departures of Ke’Bryan Hayes, David Bednar, and Isiah Kiner-Falefa via trade—and the loss of free agents Andrew Heaney, Andrew McCutchen, and Tommy Pham—freed up roughly $30 million annually for 2026–29, more than enough to cover the arbitration portion of a Skenes extension.
For 2030 and beyond, Bryan Reynolds’s last guaranteed season is 2030, with club options for 2031 at $15 million and $20 million. Mitch Keller’s contract rises each year until 2029, when he makes $20 million before becoming a free agent in 2030. If the Pirates were to move Reynolds before 2030, you begin to see where the money for Skenes could be carved out. It’s not perfect math, but it shows that the current ownership theoretically has the financial runway for such a commitment without significantly increasing overall payroll.
But there’s a major wildcard: the potential 2027 lockout. No side wants it, but based on recent negotiations in Las Vegas, both sides are far apart. It’s no secret that the league and ownership would prefer a salary-cap system. We have a historical precedent: the NHL lockout of 2012 led to a salary cap and temporarily deflated salaries, though some pre-lockout contracts still rank among the richest in that league.
Depending on how risk-averse a player is next season, signing an extension could serve as a hedge against potential new economic structures in baseball—ensuring future earnings if the union can’t prevent a cap/floor system. Likewise, small-market teams could use large contracts to help ensure they meet future spending floors with players who actually matter to the franchise, instead of, say, signing Luis Severino at the last minute.
So should the Pirates sign Skenes long term? Absolutely.
Will they be able to sign Skenes long term? Probably not.
But there’s far more potential than usual—given the unique crossroads the sport finds itself at, the Pirates’ sudden availability of long-term payroll space, and Skenes’s unprecedented excellence this early in his career.
