Paul Skenes Has Delivered, Now It's the Pirates' Turn

The Front Office's Stance

So far, the Pirates have been equally forceful in shutting down the speculation surrounding its superstar pitcher.

Pirates General Manager Ben Cherington addressed the topic at the MLB General Managers meetings, stating plainly, "Paul Skenes is going to be a Pirate in 2026".

He acknowledged that other teams regularly inquire about Skenes' availability, a testament to his immense value, but characterized those conversations as "always respectful" and "always short," with a "consistent" answer from the Pirates.

According to sources, the Pirates intend to be active in free agency this offseason — a notable departure from their approach over the last decade. The left side of the infield and corner outfield positions appear to be clear areas of need, though the organization has not signed a free-agent hitter to a multi-year deal since December 2015, when they inked John Jaso to a two-year, $8 million contract.

A significant indicator of the Pirates' commitment will be their willingness to offer multi-year contracts. Cherington revealed in an August interview with MLB Trade Rumors that the team has, in fact, extended multi-year offers to free agents in recent years, but none have been accepted. This history underscores a persistent challenge in attracting top talent to Pittsburgh.

The club's last significant free-agent coup from the upper tier of the market was a decade ago, when they signed Francisco Liriano in 2014 — the last time they inked a player who had rejected a qualifying offer from his previous team. This offseason will test whether the allure of playing alongside a generational talent like Skenes can finally change that pattern.

Cherington acknowledged the challenge but expressed cautious optimism, stating, “We have tried. It's bound to happen; the odds increase a little bit each offseason with the combination of players seeing the strength of our pitching and the opportunity to win with that pitching foundation, and a little bit more flexibility. I think the combination of those two things give it a better chance, but we'll find out. The bottom line is we want to add to our position player group and we’ll explore all kinds of ways to do that.”

While the exact budget remains uncertain, sources estimate the Pirates could have roughly $30–40 million in additional available payroll for 2026. The trade deadline departures of Ke’Bryan Hayes, David Bednar, and Isiah Kiner-Falefa freed up significant salary space last season, while free agents Andrew Heaney, Andrew McCutchen and Tommy Pham accounted for approximately $14 million.

Coming off a 71–91 record in 2025 — their seventh consecutive losing season and tenth straight year without a playoff appearance — the urgency to improve is clear.

As Cherington put it, “We need to win more games, and believe we'll have flexibility to pursue some things in free agency and trades. We need to add to the offense and we'll be disappointed if we don't; what that looks like, we don't know. We'll pursue lots of stuff, I’m sure.”

The Weight of Expectations

The trade rumors highlight the immense pressure on the Pirates organization to build a winner around Skenes before he's eligible for free agency in 2029. His individual accomplishments are staggering. Through his first two seasons, Skenes has already won the NL Rookie of the Year, been an All-Star starter twice, and now has a unanimous Cy Young Award. He has maintained a career 1.96 ERA over his first 55 starts, a feat that places him among the most dominant pitchers to begin a career in the modern era.

Quite simply, the Pirates have been blessed with a once-in-a-generation type pitcher.

Despite this historic performance, the Pirates were out of the playoff race by mid-season. This disconnect between Skenes' personal success and the team's struggles is the core of the issue. He has made his ultimate goal clear, stating, "What else do I have to accomplish in this game? A World Series championship". However, this is a goal he cannot achieve alone.

The narrative is clear. Paul Skenes has delivered on every promise, from his college championship to his major awards, and has publicly committed his future to Pittsburgh. The question is no longer about what he must do, but what the Pirates' front office will do. The team has spoken about wanting to invest more, but as Skenes himself has said, "talk is cheap".

This offseason represents a critical test of the organization's true commitment to winning. To avoid wasting the prime of a historic talent, they have to aggressively invest in building a legitimate team around him. If they don't, the chatter surrounding Skenes going to a larger market with a more committed franchise to winning, will only grow louder.