Pirates insider pours cold water on Paul Skenes extension dreams

Paul Skenes extension talk is easy to fall into because what else are fans supposed to do when the Pirates finally hand out a franchise-shifting commitment? Konnor Griffin gets nine years and suddenly the imagination starts sprinting. If the Pirates are willing to think big once, why not do it again with the most important player in the organization?

Jason Mackey of MLB.com pretty much ruined the fun this week when he addressed whether the Griffin deal could open the door to a Skenes extension. Mackey dismissed the idea because the math doesn’t make sense, the timing is even worse, and the type of contract it would take to get Skenes to even listen may sit in a financial neighborhood the Pirates have never really shown they want to visit. 

We can talk ourselves into the emotional side of this all day. We can say Griffin’s deal shows the Pirates are finally serious. We can even say that if this team starts winning, the conversation with Skenes at least becomes more believable. Mackey made that point too, noting that Skenes has previously prioritized winning over contract talk. 

Believable and doable are not the same thing. Skenes will be three years from free agency after the 2026 season.

Pirates insider reveals discouraging obstacle in any Paul Skenes extension talk

Mackey laid it out cleanly. If Skenes keeps tracking like the type of ace everyone thinks he is, he is not heading toward a normal extension number. He is heading toward something that should clear Gerrit Cole’s nine-year, $324 million deal and Yoshinobu Yamamoto’s 12-year, $325 million guarantee in total free-agent dollars for a pitcher outside the Shohei Ohtani universe. Mackey also pointed out that multiple pitchers have already crossed the $40 million average annual value threshold, including Zack Wheeler at $42 million. 

For the Pirates, buying out arbitration is one thing. Buying out arbitration while also convincing a superstar ace to surrender prime free-agent years is a completely different animal. Mackey estimated that just sketching out the arbitration side with some inflation could put the total around $96 million, and once two free-agent years are added, the guarantee jumps to roughly $176 million for only two extra seasons. His conclusion was pretty blunt: tough to see how the Pirates thread that needle. 

This is what happens when a small-market club waits until a player becomes a full-blown supernova. The longer Pittsburgh waits to prove it can win consistently, the less leverage it has in any long-term conversation. By the time the idea feels urgent, it may already be financially out of reach.

The Griffin deal is still meaningful. And it should be celebrated. But it does not automatically mean Skenes is next, and it definitely does not mean Pittsburgh has suddenly solved the biggest problem in this whole discussion.