Pirates Predicted to Lose $1.1 Million Cy Young Winner Skenes After Konnor Griffin Extension

Pittsburgh's decision to lock up top prospect Griffin could force them to trade away star pitcher Skenes.

Apr. 3, 2026 at 4:36pm

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A cubist-style painting depicting a baseball pitcher's throwing motion broken down into sharp, overlapping geometric shapes in muted earth tones, conceptually representing the difficult decision facing the Pittsburgh Pirates organization.The Pirates' difficult choice between their star pitcher and top prospect will reshape the franchise's future.Today in Pittsburgh

The Pittsburgh Pirates have reportedly extended top prospect Konnor Griffin for 9 years and $140 million, but this move could lead to the team losing their current ace, 2-time All-Star and Cy Young winner Paul Skenes. According to analysts, the mid-market Pirates will likely be unable to afford to re-sign Skenes when his contract expires in 2030, forcing them to trade him before then.

Why it matters

The Pirates are in a difficult position, having to choose between keeping their current star pitcher Skenes or investing in their future with Griffin. This decision will have major implications for the franchise's competitiveness in the coming years, as Skenes is one of the best pitchers in baseball.

The details

Skenes, who won the Cy Young award last season with a 1.97 ERA and 216 strikeouts, is projected to command a 13-year, $507 million contract on the open market. The Pirates, as a mid-market team, will likely be unable to match that price tag, especially after committing $140 million to Griffin. The team is expected to trade Skenes at the 2029 deadline, giving them 2.5 more seasons with the dominant right-hander.

  • Skenes has 4 years remaining on his current contract with the Pirates, including the 2026 season.
  • The Pirates extended top prospect Konnor Griffin for 9 years and $140 million this offseason.

The players

Paul Skenes

A 2-time All-Star and Cy Young award winner, Skenes is considered one of the best pitchers in baseball. He led the NL in ERA, strikeouts, and WHIP last season.

Konnor Griffin

The Pirates' top prospect, who they recently extended for 9 years and $140 million, signaling their commitment to building around him for the future.

Bob Nutting

The owner of the Pittsburgh Pirates, who has the financial resources to potentially keep Skenes but may choose to trade him due to the team's mid-market status.

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What they’re saying

“Life comes at you fast. Pittsburgh only has Paul Skenes under lock and key for another four years, including 2026. That feels like forever, but it's not. And while the Pirates were able to hammer out an extension for Griffin, there's almost zero chance Skenes accepts anything remotely similar. He has shown too much already; he's got a Cy Young award on his shelf and he'll probably win a couple more at this rate. Pittsburgh has the best pitcher in the National League and ownership knows, in its heart of hearts, this is a three- to four-year window. There's no way the Bucs can afford Skenes on the open market in 2030.”

— Christopher Kline, FanSided Writer

What’s next

The Pirates will likely look to trade Skenes at the 2029 trade deadline, as they will be unable to afford to re-sign him when he hits free agency after the 2030 season.

The takeaway

The Pirates are facing a difficult decision between keeping their current star pitcher Skenes or investing in their future with prospect Griffin. This move highlights the challenges small-market teams face in retaining top talent, and the tough choices they must make to remain competitive.