
As the MLB season progresses and teams assess their performances, executives are voicing a desire to shift the trade deadline further into the season. This potential change aims to provide clubs with more time to evaluate whether they should act as buyers or sellers. Currently, on August 17, several teams find themselves wishing for a trade deadline do-over. With such small sample sizes since the deadline, some decisions are already starting to loom large in the rearview mirror. Here’s a closer look at five teams regretting their trade deadline moves.
Pittsburgh Pirates: A Bullpen Overhaul Gone Wrong
The Pittsburgh Pirates entered the season with aspirations of reaching the postseason for the first time since 2015. In an aggressive push to solidify their bullpen, they made key acquisitions before the trade deadline. Yet, as of now, the results have not been promising. The Pirates currently sit at 61-65, 6.5 games out of the final wild-card spot in the National League.
Luke Weaver, brought in from the New York Mets, has had a rocky start, making only three appearances and struggling in his latest outing against the Boston Red Sox. Meanwhile, Camilo Doval, acquired from the Yankees, has faced challenges of his own, walking at least one batter in five consecutive appearances. On a brighter note, 39-year-old Kirby Yates has shown promise with a 2.89 ERA in his initial appearances, but the team’s core has not delivered as expected. With their main players either underperforming or dealing with injuries, the Pirates may regret not exploring opportunities to sell off impending free agents like Brandon Lowe and Gregory Soto.
Detroit Tigers: The Case of Tarik Skubal
The Detroit Tigers are another team that could face regret over their trade deadline decisions. The decision to move two-time defending AL Cy Young Award winner Tarik Skubal to the Los Angeles Dodgers has cast doubt among fans and management alike. While there were indications that president of baseball operations Scott Harris may not have been permitted to make a competitive offer for Skubal, there remains a lingering question about what could have happened had they held onto him until the last minute. Trading Skubal left the team vulnerable, especially since they are now just one game back of the final wild-card position in the AL.
Furthermore, the Tigers also dealt Casey Mize to the San Diego Padres, and the question arises: what if they could have built a formidable pitching rotation with Skubal, Mize, and Framber Valdez? While the long-term strategy may have been logical, the immediate impact is undoubtedly concerning as they ponder missed playoff opportunities this season.
Baltimore Orioles: Selling While Contending
The Baltimore Orioles share some similarities with the Tigers, as they also entered the season with high expectations but have underperformed. Despite being in control of the final wild-card position in the American League, the Orioles opted to make trades that raised eyebrows among fans. The decision to trade Taylor Ward to the Seattle Mariners drew scrutiny, especially in light of what they received in return. RHP Alex Hoppe, who has struggled with a 5.17 ERA, along with two minor leaguers, seems like a low return for a player of Ward's caliber.
Ward’s experience and ability to draw walks—leading the AL with 87 walks—could have made a significant difference down the stretch for a team still vying for contention. While the deal might make sense in terms of future planning, it raises questions about the team's commitment to their current competitive window.
New York Yankees: Mixed Results from Recent Acquisitions
The New York Yankees made headlines by acquiring Luis García Jr. and Heliot Ramos, anticipating that both would bolster their lineup. However, frustrations have mounted as García has struggled to adapt to his new environment, posting a disappointing .653 OPS since arriving. Ramos has fared even worse, managing only a .063 batting average with the Yankees in his first ten games.
Injuries to key players like Aaron Judge and Giancarlo Stanton have compounded the Yankees’ issues, making it imperative for new acquisitions to contribute right away. The Yankees’ decision to part with promising prospects to acquire Ramos—who had a history of performing well against left-handed pitching—makes the situation all the more pressing for the team. If they fail to find the right solutions, the playoff hopes could dim quickly.
Kansas City Royals: Holding Onto Aging Assets
Finally, the Kansas City Royals have found themselves in a precarious position after witnessing another disappointing season. Despite their storied history of contending, they currently hold a record of 51-74. In hindsight, it may have been prudent for the Royals to field offers for veteran pitchers Michael Wacha and Seth Lugo before the trade deadline.
Both pitchers are under significant contracts but have not contributed to a competitive season. Wacha and Lugo's age could mean declining performance, and keeping them risks further complications for a team still in need of retooling. By addressing trade opportunities earlier, the Royals could have fortified their prospects and built for a brighter future.
As the 2023 MLB season progresses, teams that made questionable trade decisions may wish they had waited longer to assess their needs. As the adage goes, timing is everything in sports. Whether it's fortifying a roster or deciding to sell, the upcoming weeks will be crucial for these franchises.

