With the trade deadline fast approaching, the Philadelphia Phillies will be looking to make some big moves to bolster their roster ahead of a potential deep playoff run. The Phillies have made numerous trade deals at the deadline over the years. Some of them have worked out better than planned, whereas everyone probably wishes others never happened.
In recent times, the trade with the Pittsburgh Pirates that brought Rodolfo Castro to the Phillies in exchange for pitcher Bailey Falter in 2023 could fall under this category. Castro provided all of three hits, two runs and two RBIs in his 14-game stint with the Phillies in 2023. Falter has gone on to become a mainstay in the Pirates rotation, currently sporting a solid 7-5 record with a 3.82 ERA and 1.18 WHIP in 2025.
But of course, that move is likely nothing compared to some of the atrocious deals made at the deadline by Philadelphia in the past. As a result, let’s take a look back at five of the worst trade deadline moves that the Phillies have made in the recent history of the franchise.
5 of the worst trade deadline deals in Philadelphia Phillies history
2000: Phillies trade Curt Schilling to the Arizona Diamondbacks for Omar Daal, Nelson Figueroa, Travis Lee and Vicente Padilla
Philadelphia may have gotten the steal of the century when they acquired future ace Curt Schilling from the Houston Astros for Jason Grimsley. But they sure gave a lot of that away during the summer of 2000. Amidst their seventh consecutive losing season, the Phillies traded away Schilling to the Arizona Diamondbacks for what turned out to be an underwhelming return package.
Right-hander Nelson Figueroa and left-hander Omar Daal would be gone after just one and two seasons, respectively. Former NL Rookie of the Year finalist first baseman/outfielder Travis Lee lasted three solid years with the Phillies, posting a .258 average and .745 OPS with 149 runs scored, 34 home runs and 174 RBIs in 366 games. Finally, right-hander Vicente Padilla at least helped cushion the blow by staying with Philadelphia for six seasons and pitching in the capacity of both a reliever and a starter. In 162 games, Padilla amassed a 49-49 record with a 3.98 ERA and 1.34 WHIP. However, the Phillies failed to make the postseason during all of those years.
On this date back in 2000, the #Dbacks traded for RHP Curt Schilling.
— Arizona Diamondbacks (@Dbacks) July 26, 2018
He proceeded to make an unforgettable impact in the desert, earning a spot on the #GenerationDbacks 20th Anniversary Team: https://t.co/ztE5zAC9gV pic.twitter.com/XKJwfBmqHo
As for Schilling, let’s just say he transformed himself into one of the top pitchers in all of baseball during his time with the Diamondbacks. In his four years with Arizona, he went a stunning 58-28 with a 3.14 ERA and 1.03 WHIP, with a whopping 875 strikeouts in 781 2/3 innings. In doing so, Schilling was a two-time All-Star and finished runner-up for the NL Cy Young Award twice.
More importantly, he helped the Diamondbacks to their first and only World Series title in 2001. Just for good measure, Schilling would go on to help the Boston Red Sox to their second World Series win in four years in 2007, proving that he definitely was a winner. Perhaps keeping Schilling could have netted the Phillies with a championship earlier than the one they finally got in 2008.