2006: Phillies trade Bobby Abreu and Cory Lidle to the New York Yankees for C.J. Henry, Matt Smith, Jesús Sanchez and Carlos Monasterios
As one of the main offensive forces for the Phillies during the early 2000s, Bobby Abreu’s tenure with the club concluded when he was dealt along with the late Cory Lidle to the New York Yankees for a plethora of prospects at the 2006 trade deadline. For someone of such great value to the team, Philadelphia ultimately ended up getting the short end of the stick as none of the prospects in the return package materialized into any player of significance, with shortstop/outfielder C.J. Henry and right-hander Jesús Sanchez failing to even to appear in a single MLB game.
For Lidle, the right-hander registered four wins for the Yankees down the stretch in 2006 before suffering his fatal plane accident after the conclusion of the MLB season that year. Abreu put up three straight double-digit home run and 100+ RBI seasons while maintaining a solid batting average above .280 and an OPS above .800. He also helped the Yankees to two postseason berths, along with another one with the Los Angeles Angels in 2009. Fortunately for the Phillies, they still managed to win their second ever World Series in 2008 without Abreu to make the dreadful trade just a little more palatable.
2015: Phillies trade Cole Hamels, Jake Diekman and cash to the Texas Rangers for Matt Harrison, Jake Thompson, Alec Asher, Jerad Eickhoff, Jorge Alfaro and Nick Williams
Perhaps one of the worst trade deals ever made by the Phillies, and not just at the trade deadline, occurred when they shipped out franchise ace Cole Hamels in 2015 — right after he threw a no-hitter. With hopes of helping with their rebuild, it instead turned into a total disaster.
With Hamels’ pedigree at the time, one would have expected that any pieces Philadelphia would get in the return should help them fast-track their rebuild. However, it actually ended up prolonging it until the eventual arrivals of Bryce Harper, J.T. Realmuto and company in the late 2010s.
Check out Cole Hamels & the @Phillies' reaction today after the final out of his no-hitter at Wrigley on #BallparkCam pic.twitter.com/6Ws0QnxFJR
— MLB Network (@MLBNetwork) July 26, 2015
One of the big pieces that came back to the Phillies was former All-Star and 18-game winner left-hander Matt Harrison. He never appeared in a game for Philadelphia and actually ended up retiring after the 2015 season due to recurring back issues. Right-hander Jake Thompson and outfielder Nick Williams would both spend three unspectacular seasons with the Phillies before eventually pursuing a career in foreign and independent baseball leagues even up until today. Right-hander Alec Asher made 12 starts for Philadelphia, posting a 2-7 record with a less-than-stellar 5.88 ERA before moving on to the Baltimore Orioles, Los Angeles Dodgers and Milwaukee Brewers organizations and left professional baseball completely after 2019.
Both right-hander Jerad Eickhoff and catcher Jorge Alfaro would at least give back a bit of value to the Phillies. Eickhoff was part of the Phillies' rotation for five seasons, posting a respectable 21-30 record with a 4.15 ERA and 396 strikeouts in 440 innings pitched. Alfaro was one of the top young pieces that the Phillies received from the Rangers. But he only spent three years here, compiling a .270 average with 47 runs scored, 15 home runs and 51 RBIs over 143 games.
For Hamels, he ended up leading the Rangers to two straight postseason appearances, along with becoming an All-Star for the fourth time in his career in 2016. The veteran lefty extended his MLB career all the way to 2020 with stops in Chicago and Atlanta before injury woes took over and eventually forced him to retire.
Just to add on to the atrocity of the trade, reliever Jake Diekman went on to become a reliable piece out of the Rangers bullpen for four seasons, helping with their playoff runs as well. And if that wasn’t enough, the Phillies also sent cash to Texas to make it one of the worst moves in franchise history.