Like any other franchise, the Philadelphia Phillies have made a huge number of trades during the 21st century. This offseason, the Phillies acquired starting pitcher Jesús Luzardo in a deal with the Miami Marlins. More recently, on Wednesday, they dealt Tyler Gilbert was dealt to the Chicago White Sox. Some of these trades have led to success for the Phillies, while others have set the team back. After looking at the Phillies’ best free agent signings since 2000 it is now time to evaluate their best trades in that time span.
The 5 Best Phillies Trades of the Century
5. Sending Jimmy Rollins to the Los Angeles Dodgers
This is the lone deal on this list involving the Phillies trading away a star player. On Dec. 19, 2014, the Phillies sent Rollins and cash to the Dodgers for Windle and Eflin. Rollins had a .224/.285/.358 line with 13 home runs and 41 RBI in 144 games as a Dodger. Furthermore, Rollins had a 0.4 bWAR and a 79 OPS+ in that 2015 season. Eflin would become a key part of the Phillies’ 2022 run to the World Series. In six appearances between the NLCS and World Series that year, he did not allow an earned run. Eflin also recorded a save in the NL Wild Card Series.
4. Acquiring Cristopher Sánchez from the Tampa Bay Rays
On Nov. 20, 2019, the Phillies and Rays made what appeared at the time to be an insignificant trade. Neither Sánchez nor Mead had played in the majors at that point. Now, Sánchez is becoming one of the better starting pitchers in baseball. He made the All-Star team in 2024 in a season where he pitched two complete games. Mead has 62 career major league appearances across the 2023 and 2024 seasons. This is one of the more underrated one-for-one trades in the last few years.
3. Acquiring Brad Lidge from the Houston Astros
Phillies Received: Brad Lidge + Eric Bruntlett
Astros Received: Michael Bourn + Mike Costanzo + Geoff Geary
It is reasonable to believe the Phillies would not have won the 2008 World Series if Lidge was not on the team. On Nov. 7, 2007, the Phillies sent Bourn, Costanzo, and Geary to the Astros for Lidge and Bruntlett. In 2008, Lidge had a 1.95 ERA and went 41-for-41 in save attempts. He finished fourth in NL Cy Young Award voting and eighth in NL MVP voting. Over 9 1/3 innings that postseason, Lidge allowed a lone run in the NLDS. and recorded seven total saves. In addition, he had a 11.8% cWPA in the 2008 World Series.
2. Acquiring J.T. Realmuto from the Miami Marlins
Marlins Received: Will Stewart + Jorge Alfaro + Sixto Sánchez + international bonus slot money
This trade is a more recent example of a blockbuster fleece. On Feb. 7, 2019, the Phillies got Realmuto from the Marlins in exchange for Stewart, Alfaro, and Sánchez, along with international bonus slot money. Sánchez was viewed as the centerpiece of the Marlins return and massively underperformed. Realmuto became an important player in the Phillies’ 2022 pennant run. A few weeks after this deal, they signed Bryce Harper. Those two moves laid the foundation for the current team.
1. Acquiring Roy Halladay from the Toronto Blue Jays
On Dec. 16, 2009, the Phillies made a trade for Halladay that saw d’Arnaud, Drabek, and Taylor go to the Blue Jays. Halladay made the first postseason appearance of his Hall of Fame career in a Phillies uniform in 2010. In that first postseason outing, he pitched a no-hitter, the second in MLB postseason history after Don Larsen‘s perfect game in the 1956 World Series. Having also pitched a perfecto himself that May, Halladay won the NL Cy Young Award in 2010 and also finished as the runner-up in 2011. In each of his first two seasons in Philadelphia, he recorded an 8.0 bWAR or better. Halladay had a 2.37 ERA in five postseason starts.