Paul Skenes and the Pittsburgh Pirates can say all the right things, but all parties have also acknowledged the multi-million-dollar element in the room. With the Pirates going through another rebuild and having just finished their ninth losing season in 10 years, questions have understandably mounted about how much longer Skenes, a two-time All-Star and arguably baseball’s best starting pitcher, will play in Pittsburgh.
Shortly before Skenes unanimously won the Cy Young Award this week, a report emerged that the 2023 No. 1 pick has told teammates he wants to play for the New York Yankees. NJ Advance Media quoted an anonymous Pirates player, who also shared that Skenes wants to be traded before hitting free agency after the 2029 season.
It’d be hard to blame any team wanting to acquire Skenes, even if it meant giving up numerous top-5 prospects. The 23-year-old Skenes has a 1.96 ERA and a 386-74 K-BB ratio over 320 2/3 big-league innings. His 7.7 bWAR ranked fourth leaguewide this season, and he finished tied for sixth in NL MVP voting; he and Arizona Diamondbacks center fielder Corbin Carroll each earned 83 votes.
Skenes reiterated that his goal is to win with the Pirates, and general manager Ben Cherrington told reporters in Las Vegas that the organization will not trade Skenes this offseason. However, that won’t stop the trade speculation, though the Yankees aren’t the team that baseball fans should be worried about.
Could the Pirates trade Paul Skenes to the Angels or Dodgers?
Paul Skenes tonight:
— Platinum Key (@PlatinumKey13) September 5, 2025
6.0 IP, 2 H, 0 R, 1 BB, 8 SO
94 pitches, 65 strikes, 13 whiffs
HE HAS A 1.98 ERA THIS SEASON. JUST MADE THE DODGERS LOOK LIKE NOTHING. NL CY YOUNG. NOW. pic.twitter.com/Aur59tYnSc
Long before becoming one of Major League Baseball’s premier players, Skenes grew up in Lake Forest, Calif, roughly half an hour from Angel Stadium. He spent his childhood as an Angels fan and even attended Shohei Ohtani’s first home pitching start in April 2018.
Could Skenes return to California and live out a childhood dream by playing for the Angels? It’s worth noting that when the Angels hosted the Pirates this past April, Skenes did not pitch during that series. However, he told reporters it’d be a few years before he got to pitch “at home,” in reference to Angel Stadium.
Then, there’s Ohtani and the Dodgers, the two-time defending World Series champions who have never shied away from blockbuster trades and signing top-tier free agents, including Ohtani, first baseman Freddie Freeman, and 2025 World Series MVP Yoshinobu Yamamoto.
Although Cherrington is steadfast in saying that Skenes will remain in Pittsburgh to open the 2026 season, it’s fair to wonder if he’ll change his mind for the right trade package. MLB Pipeline listed the Dodgers’ farm system as the best in baseball after this past deadline, with three players — outfielders Josue De Paula (No. 12) and Zyhir Hope (No. 19), and infielder Alex Freeland (No. 43) — ranking inside the top 50.
Here’s a potential nightmare scenario for baseball fans: The Dodgers acquire Skenes within the next 12 months, buy out his arbitration years, and sign him to a massive, long-term contract. Considering their penchant for filing out blank checks, would anyone truly be surprised to see the Dodgers give Skenes a 10-year contract exceeding $500 million, if not more?
The unfortunate reality is that with players like Skenes, we collectively start discussing them as trade candidates so early in their careers because of the situation they’re in. Skenes is an elite All-Star playing on a team that regularly fields one of the sport’s lowest payrolls and has only reached the NLDS once in three decades. The clock is ticking on where Skenes will pitch next, and it’s not unrealistic to imagine that he’s eventually California-bound.