The Pittsburgh Pirates’ front office is already turning toward the future, and one name stands out: Paul Skenes. In a recent media session, GM Ben Cherington acknowledged the possibility of an extension for the young ace–though he emphasized that discussions haven’t formally begun.
Skenes’ 2025 campaign was nothing short of spectacular: a 1.97 ERA across 187.2 innings, 216 strikeouts vs. just 42 walks, a .199 opponent average, and a WHIP of 0.95. He even set a franchise mark: the most strikeouts by a right-handed pitcher in the live-ball era. Those numbers make an “extension or bust” narrative feel natural, and Cherington didn’t shy away from acknowledging that Skenes is at the center of franchise thinking.
“Well it’s obvious that on and off the field he is someone we would want to have for as long as possible,” Cherington said. “Every team would say that. He exemplifies in my experience with him, he lives, he walks the walk in every possible way and we need, not every player would do it quite at the level he does but we certainly need even more of that mindset and just approach toward his craft, his approach toward winning, on top of the stuff he does off the field.”
Performance Demands Reward, But Timing Is Key
It’s clear that the Pirates would prefer to “buy out” some of Skenes’ arbitration years, locking him in before he reaches free agency. Doing so would insulate Pittsburgh from bidding wars and allow them to pay a premium earlier while avoiding full market escalation. But Cherington reminded reporters that formal talks have yet to begin, and that it’s not unusual for contract issues to arise “every year” with key players.
Cherington’s praise for Skenes went beyond the box score. He lauded the pitcher’s character, work ethic, and the value he brings off the field. “He walks the walk … he lives, he walks the walk in every possible way,” Cherington said. That kind of endorsement isn’t just PR; it’s often the precursor to serious negotiations.
Walks off the Mound. Takes it all in. 1.97 ERA.
Cy Young. 👏👏👏
Yet it’s worth noting the financial reality: after one more pre-arbitration season (2026), Skenes will enter three arbitration years before reaching free agency in 2030. The Pirates, with their historically tight payrolls, will likely explore creative structures if and when extension talks start in earnest.
“He’s clearly someone that is at the center of our thoughts a lot,” Cherington said. “He wants to win really badly too. I expect that at some point every year you talk about contract, you talk about contract with everybody so that’s going to come for us at some point anyway and of course he’s someone we’d love to have here for a long time.”
Risks, Leverage & Future Scenarios
From Skenes’ perspective, the leverage is limited now; he’s not arbitration-eligible yet, and there’s modest upside to waiting. But if he continues his elite performance, he could price himself out of what Pittsburgh is comfortable paying. The club would risk losing him in free agency, or being forced into a deal far more expensive than what they might negotiate today.
All 216 of them.
NL CY YOUNG. NOW.
For Pittsburgh, the question isn’t just about paying a star. It’s about balance. Can they sign Skenes to a team-friendly long-term deal and keep flexibility elsewhere on the roster? The ideal scenario would bridge both competitiveness and fiscal prudence.
Another wrinkle: injury risk. Even ace pitchers can stumble. By waiting, Pittsburgh preserves some protection against downturns. But waiting too long could also cost them. It’s a delicate balance.
Pirates GM Ben Cherington Weighs in on Possible Paul Skenes Extension