Skenes and Skubal: Cy Young Winners at Career Crossroads
In a significant milestone for both their careers, Paul Skenes of the Pittsburgh Pirates and Tarik Skubal of the Detroit Tigers were crowned the National and American League Cy Young Award winners respectively on Wednesday. Their exceptional performances throughout the 2025 season have not only earned them baseball’s highest pitching honor but have also placed them at the center of swirling offseason trade speculation. Skenes, the Pirates’ phenomenal rookie, achieved a historic feat by becoming the first pitcher since Dwight Gooden to capture both the National League Rookie of the Year and Cy Young Award. His dominance was evident in his league-leading 1.97 ERA and impressive 216 strikeouts. For a Pirates team that struggled to a 71-91 record and finished last in the NL Central, Skenes represented a rare bright spot and hope for the future.
Detroit’s Skubal joined an elite group of pitchers by securing back-to-back Cy Young Awards, cementing his status as one of baseball’s premier hurlers. His 2.21 ERA topped the American League while his 248 strikeouts demonstrated his overwhelming ability to dominate opposing hitters. Unlike Skenes, Skubal’s individual excellence translated to team success as the Tigers reached the postseason with an 87-75 record, though their October journey ended prematurely with a division series loss to the Seattle Mariners. Both pitchers’ remarkable achievements have transformed them from mere star players to franchise cornerstones with immense trade value—setting the stage for what could be a fascinating offseason of negotiations and decisions.
Despite Pirates general manager Ben Cherington’s firm declaration that “Paul Skenes is going to be a Pirate in 2026,” rumors continue to circulate about the young ace’s future. A report from NJ Advance Media cited a former Pirates teammate claiming Skenes “wants to play for the Yankees” and is “hoping for a trade” before his free agency arrives in 2029. While Cherington dismissed these rumors, he acknowledged their existence, saying, “I understand it.” The report also mentioned the Los Angeles Angels as a potential destination given Skenes’ California roots and childhood fandom of the team. For a struggling Pirates franchise, the temptation of a potential “Godfather” offer from a team with a deep farm system could test their resolve to keep their young superstar.
Skubal’s situation with the Tigers appears more fluid, with reports suggesting Detroit will “at least listen” to offers for their back-to-back Cy Young winner, though they would need to be “blown away” by a potential deal. Both the Los Angeles Dodgers and Boston Red Sox—franchises with significant resources and a history of pursuing elite pitching—have already been mentioned as possible suitors for the left-handed ace. Tigers general manager Jeff Greenberg has taken a more guarded approach, refusing to reveal whether Skubal or other Tigers players have been mentioned in trade discussions. This measured stance leaves the door open for potential moves while maintaining negotiating leverage as the hot stove season heats up.
The contrasting approaches of the Pirates and Tigers organizations reflect the difficult balancing act small and mid-market teams face when developing homegrown superstars. Pittsburgh, having endured years of rebuilding, faces immense pressure to demonstrate they can build a competitive team around Skenes rather than continuing their historical pattern of trading away stars for prospects. Cherington’s emphatic statement about keeping Skenes signals both commitment to their ace and awareness of fan frustration with previous departures of franchise players. The Tigers, having tasted postseason action with Skubal leading their rotation, must weigh the immediate benefits of his dominance against the potential long-term value of prospects who could sustain competitiveness over many years.
As the MLB winter meetings approach, these Cy Young winners represent two of the most compelling storylines in baseball. Their situations epitomize the fundamental tensions within the sport—between small market realities and big market ambitions, between present success and future potential, between keeping homegrown stars and maximizing return on baseball assets. For fans of the Pirates and Tigers, the uncertainty creates both anxiety and excitement about their teams’ directions. For the broader baseball world, the possibility of seeing either or both of these pitching phenoms in new uniforms next season adds intrigue to an already fascinating offseason. While both organizations have signaled their intentions, the baseball adage remains true—until spring training begins, anything can happen in the unpredictable world of MLB player movement.
