The 2025 season has come to a close in Pittsburgh, Pennsylvania, in a timeline that has become all too familiar for the Pirates faithful.
With a 71-91 record on the season, it marks the seventh consecutive season finishing under .500 on the year, and tenth season missing the postseason.
Pittsburgh finished the year with the worst team OPS in baseball at .655, with just 117 total homers for the club. The second-worst slugging team in baseball, the St. Louis Cardinals, finished with 148 long balls in comparison.
While there may not have been much to celebrate, one man gave Pirates fans something to tune in for every fifth game.
That was Paul Skenes, who has completed one of the best seasons for a 23-year-old in MLB history.
Skenes finished his first full season in the bigs with a 1.97 ERA in 32 starts with 216 strikeouts. This ERA, alongside his ERA+ (217), Fielder Independent Pitching (2.36), and Homeruns Per Nine Innings (0.5) all led baseball.
The soon-to-be Cy Young winner did this after his Rookie Of The Year 2024 campaign, where he had a 1.96 ERA in 23 starts after being called up midseason.
This gives him a career ERA of 1.96 in 55 outings, all before turning 24-years-old.
With this start to his young career, Skenes is the first pitcher 24-years or younger since 1908 to have a sub-2 ERA in their first 50 starts.
All five other members are from the dead-ball era, where the average runs per game league-wide was 3.60. In the past two years, the average runs per game in MLB is 4.42, which would mean Skenes’ 1.96 ERA over this span would be a 1.60.
The former first overall pick has already delivered on his draft return, and the Pirates still have team control over their ace for the next four years.
Even though the typical advice for a team in Pittsburgh’s position is to capitalize on having Skenes at his age and price tag, and build a team around him.
However, with the track record of young talent to once wear the black and yellow, is there an argument that the Pirates should try and extend Skenes already?
If a team wants to extend a young prospect, they usually attempt to do so either when they are in the Minors or before they officially establish themselves as an MLB-caliber player.
Because Skenes spent so little time in MILB, only starting 12 games before getting the call, and then dominating upon arrival, the Pirates never had an opportunity to even consider these ideas.
Now, after two of his six years of arbitration have been completed, the Pirates have yet to even finish with a positive record behind Skenes.
Pittsburgh does have the ninth-ranked farm system in baseball, however the team does not seem close to competing anytime soon.
Unless General Manager Ben Cherington plans on swinging big in this year’s offseason, which would be against the norm in franchise history, the Pirates seem to be looking to develop a homegrown core before spending on the rest of the roster.
If that is so, then there would be no excuse to try and lock up Skenes now to extend this four-year window.
The idea of this hypothetical signing would be in no way a “discount”. In fact, his deal could threaten some of the top-AAV contracts like Zack Wheeler, Jacob deGrom and Blake Snell.
So, the Pirates could offer Skenes a contract to take him past his current free agency date at 28-years-old.
Thankfully for the Pirates, Skenes is not represented by Scott Boras, who is notorious for never allowing his clients to sign an extension before becoming a free agent.
However, this is not going to be a deal many agents outside of Boras would consider either, unless their client does have a desire to stay.
This is why the AAV would have to be high, and would have to include player options to make Skenes not feel as trapped.
While Skenes is on pace to potentially reset the market if he were to be a true free agent, a contract along the lines of eight years, $45,000,000 AAV with a player option after his seventh year may be a safe deal to sign.
Not only would it significantly change his life now, as he just made $875,000 for his Cy Young season, but it would also give him security in his future.
It is easy to view the decision purely from an analytical view. However, the real life aspects of a decision like this need to be considered.
If Skenes enjoys the team and enjoys his life right now, and wants to be the face of a historic franchise, while not having to worry about injuries costing him money in the future, this could be all he wants. Not everyone is looking to maximize their value and spend an entire offseason negotiating their worth.
From the Pirates perspective, they will not only get to keep their superstar, but can change the narrative around their team. Whether it is Gerrit Cole, Tyler Glasnow, or Joe Musgrove to name a few, Cherington has seldom shown an ability to retain talent.
While a large portion of these trades came down to the players likely not resigning, the return for these deals are the reason why the Pirates keep playing sub-.500 baseball.
If Skenes is willing to stay, Pirates owner Robert Nutting cannot hesitate to sign the check. For a team that has consistently stayed under payroll, largely due to being a smaller market team and not being able to attract free agents, he cannot hesitate if the right hander has any desire to sign with the team.
If so, Skenes will provide a way to win, which will always make free agents want to sign, even if it is a smaller market.
If Skenes will not sign, then the next best option is to invest in the team around him and treat his arbitration years as a four-year window to win. Based on the team’s spending since their last playoff appearance, it is safe to say that they have enough saved to either extend their ace, or attack the window where he is still in your city.
2025 — Record: 71–91 (.438), Payroll: $84,423,338 (Rank: 27th)
2024 — Record: 76–86 (.469), Payroll: $85,400,989 (Rank: 28th)
2023 — Record: 76–86 (.469), Payroll: $75,695,975 (Rank: 28th)
2022 — Record: 62–100 (.383), Payroll: $56,184,032 (Rank: 29th)
2021 — Record: 61–101 (.377), Payroll: $54,356,609 (Rank: 28th)
2020 — Record: 19–41 (.317), Payroll: $25,343,022 (Rank: 30th)
2019 — Record: 69–93 (.426), Payroll: $72,176,474 (Rank: 28th)
2018 — Record: 82–79 (.509), Payroll: $91,025,861 (Rank: 27th)
2017 — Record: 75–87 (.463), Payroll: $100,503,030 (Rank: 24th)
2016 — Record: 78–83 (.481), Payroll: $99,518,136 (Rank: 24th)