The Chicago Cubs' offseason trades with the Houston Astros have not panned out as expected. Ryan Pressly, originally acquired to bolster their bullpen, has struggled this season with a 3.79 ERA and a troubling -0.2 fWAR, leading to a diminished role behind closer Daniel Palencia. Despite a strong history, Pressly's performance has raised questions about his reliability in high-leverage situations. As he approaches free agency, the Cubs may consider trading him to clear salary space and potentially acquire a prospect for the future.

Christopher Kline notes that while Pressly has shown flashes of his past form, including a decrease in his WHIP, a contender may still find him appealing as a low-cost rental. The Cubs, aiming for a competitive run, might weigh the benefits of offloading Pressly against their need for a strong bullpen. If they can secure an intriguing prospect while freeing up funds, it could be a prudent move for their long-term strategy.