No. 6—July 26, 2000
The Deal—The Phillies dealt RHP Curt Schilling to the Arizona Diamondbacks for LHP Omar Daal, RHP Nelson Figueroa, 1B Travis Lee, RHP Vicente Padilla and a bag of donuts.
This particular transaction proves that quantity does not make up for quality. None of the players obtained amounted to much of anything, while Curt Schilling went on to lead a couple teams to World Championships.
After being dealt at the 2000 trading deadline, Schilling racked up a 45-13 record in Arizona the next two seasons. Interestingly, he came in second place each year in the Cy Young voting finishing both times behind his own teammate, Randy Johnson.
The duo dominated the 2001 postseason and led the expansion team to a World Series title in just its fourth year of existence. This added insult to injury for Phillies fans who had experienced just one championship in 119 years.
While Schilling would eventually join the Boston Red Sox for the bloody sock championship ride, the Phillies put together six straight near miss seasons after his departure.
It does not take a great deal of imagination to surmise what those teams might have done if they hadn't given away one of the best pitchers in baseball.