For decades, hope has been a scarce commodity in Pittsburgh, but a new generation of talent is giving Pirates fans a reason to dream again. At the heart of the conversation sits Paul Skenes, the 23-year-old ace who has quickly established himself as one of Major League Baseball’s brightest stars. Drafted No. 1 overall just over two years ago, Skenes already boasts an NL Rookie of the Year trophy from 2024 and is a leading candidate for the NL Cy Young Award this week. His meteoric rise has made him the talk of the league—and, perhaps inevitably, the subject of persistent trade rumors swirling around the small-market Pirates.
Despite being under team control through the 2029 season, Skenes’ name has been floated in speculative trade talks by pundits and rival executives alike. The New York Yankees, ever hungry for elite pitching, have emerged as the most popular hypothetical destination. Yet, for all the noise, Pirates president of baseball operations Ben Cherington has been unwavering in his public stance. “I do dismiss it, but I understand it,” Cherington told NJ.com’s Randy Miller when pressed about a potential Skenes-Yankees deal. “What we’re going to focus on is just how do we win games with him in a Pirates uniform. I have a ton of respect for the Yankees, but we’ll just focus on what we need to do.”
That focus is more than just talk. Cherington has made it clear the Pirates intend to build around Skenes, not shop him. “In a nice way, it’s really simple because what matters most to (Skenes) is what matters to us,” he said. “Win more games. That’s the focus because that’s what is going to be most important to him. What probably gives us the best chance to keep him in Pittsburgh for longer is winning games, and that’s what we need to do anyway.”
Still, the rumor mill churns. One of Skenes’ own teammates from the past two seasons reportedly told NJ Advanced Media that the right-hander has little faith in the Pirates’ direction and is hoping to be traded well before he reaches free agency in the 2029-30 offseason. “Trust me, he wants to play for the Yankees,” the anonymous teammate claimed. “I’ve heard him say it multiple times.” The revelation has set off a firestorm of speculation—not just about Skenes’ future, but about which teammate might have leaked his desires to the media.
Theories abound. Andrew McCutchen, the franchise icon who returned to Pittsburgh for a third stint, has been publicly critical of the club’s lack of progress. “I feel like we’re beating the same drum,” McCutchen told the Post-Gazette at season’s end. “Third year back, kind of feels the same just from an instance of where we are. It does kind of feel the same. And from that, in that instance, just looking at where have we improved, or where do we need to get better? And kind of feels the same, same answers that you have internally. Yeah, it just leads me to think, like, what’s the plan moving forward, and what is it gonna look like next season?”
Despite his candor, McCutchen’s deep loyalty to the organization makes him an unlikely candidate to have leaked Skenes’ wishes. Isiah Kiner-Falefa, who spent the 2024 and part of the 2025 season with the Pirates and is a former Yankee himself, is another name in the mix. His ties to New York and familiarity with both clubs could make him a plausible source. Then there’s Tommy Pham, the outspoken clubhouse veteran who posted a .700 OPS and a 95 OPS+ in 2025. Pham, known for his fiery demeanor and willingness to speak his mind, is seen by some insiders as a likely candidate to have spoken on Skenes’ behalf. Pham remains a popular target for a 2026 return if the Pirates meet his free-agent asking price.
All this intrigue comes against the backdrop of a franchise desperate to escape decades of futility. Since Barry Bonds’ departure in 1992, the Pirates have managed just four winning seasons in 33 years, with a paltry .449 winning percentage and only three playoff wins. The 2024 campaign saw the team finish dead last in the NL Central—a familiar position that only fuels the skepticism of the fan base.
Yet, there are glimmers of optimism. Skenes was worth 6.5 fWAR in 2025, putting him squarely in the conversation among the game’s elite. If he can stay healthy and the Pirates can retain his services, he stands as a cornerstone for a potential turnaround. The organization is also pinning hopes on Konnor Griffin, a top prospect widely projected by industry experts to become a star. Should Griffin blossom alongside Skenes, history suggests the Pirates could be on the verge of something special. Teams with two 5+ WAR players rarely finish below .500, and most go on to win 90 or more games and make the playoffs.
The Pirates’ own recent history underscores this point. The last time Pittsburgh fielded two or more 5+ WAR players in a season—2013, 2014, and 2015—they posted their best records since the days of Bonds, including a 98-win season in 2015. That year, the club’s misfortune was to play in a division where three teams eclipsed 97 wins, resulting in a quick playoff exit despite a powerhouse roster. Still, the formula for success is clear: keep your stars, build around them, and hope for a little luck.
There are other reasons for cautious optimism. Bubba Chandler, one of baseball’s top pitching prospects, is expected to join the rotation in 2026. Young arms like Jared Jones, Braxton Ashcraft, and Hunter Barco have already reached the majors, with promising prospects Seth Hernandez and Edward Florentino rising through the ranks. If even a couple of these players pan out, the Pirates could soon boast one of their most talented rosters in decades.
Of course, the shadow of past heartbreak looms large. Pirates fans have learned not to get too attached to hope, lest it turn to disappointment once again. The cautionary tale of the Los Angeles Angels—who paired Mike Trout and Shohei Ohtani to little postseason success—serves as a reminder that star power alone doesn’t guarantee wins. Injuries, stalled development, and bad luck can derail even the most promising blueprints.
For now, the Pirates’ front office is sticking to its guns: Paul Skenes is not for sale, and the focus remains on building a winner in Pittsburgh. Whether the rumors of his Yankee ambitions are smoke or fire, one thing is certain—the eyes of the baseball world will be watching closely as the next chapter of this story unfolds.
With Skenes anchoring the rotation and a wave of young talent on the horizon, Pirates fans might finally have a reason to believe that better days are ahead. The only question is whether the franchise can seize the moment—or if hope will once again slip through their fingers.
