The 2025 trade deadline saw the Pittsburgh Pirates at the center of controversy, not for their notable transaction of All-Star closer David Bednar to the New York Yankees, but for their inaction regarding other players. Despite Bednar's successful move promising a solid return of three prospects, the Pirates opted not to trade rental players, including pitchers Andrew Heaney and Dennis Santana. Heaney, previously with the Yankees, has struggled this season, while Santana is enjoying a breakout year. His impressive 1.39 ERA and 36 strikeouts further enhanced his trade value, yet the Pirates held onto him, a decision that puzzled many fans. The Pirates' failure to capitalize on Santana's value may leave them empty-handed this winter, ultimately frustrating their fanbase.