Philadelphia Phillies: The 10 worst trades in franchise history

National Baseball Hall of Fame Induction Ceremony
National Baseball Hall of Fame Induction Ceremony / Mark Cunningham/GettyImages
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Phillies Trade Cole Hamels

This was a pretty brutal trade deadline deal looking back. Hamels was a mainstay in the Phillies’ rotation as a borderline ace and a consistent source of innings throughout his nine plus seasons in Philadelphia. However, the Rangers were very aggressive in trying to upgrade their rotation and Philly ended up agreeing to send Hamels and Jake Diekman to Texas for Matt Harrison, Jorge Alfaro, Jake Thompson, Alec Asher, and Jerad Eickhoff.

Jorge Alfaro had his moments, but the rest of the return for Hamels did not do much of anything for the Phillies. Hamels would pitch reasonably well for the Rangers before having a career renaissance with the Cubs. Health issues have kept him out the last few years, but that doesn’t excuse the total lack of a return despite the size of the trade package the Phillies got for one of the best pitchers in the league.

Phillies Trade Grover Cleveland Alexander

To be clear, evaluating any trade from 1917 is pretty suspect because baseball was the Wild West back then with teams having to do some pretty weird stuff to just stay afloat. No one thought that Grover Cleveland Alexander wasn’t one of better pitchers in baseball, but the owner needed money and there was a real chance that Alexander would have to go fight in World War I which carried a unique set of risks. So, Philadelphia traded him to the Cubs for Mike Prendergrast, Pickles Dillhoefer (what a name), and $60,000.

$60,000 was not a small amount of money back then, but Prendergrast and Pickles didn’t amount to much of anything in Philadelphia. Alexander, meanwhile, would go on to pitch 13 more seasons and end his career with a 2.56 ERA and almost 2200 strikeouts. In the third year of the existence of the Hall of Fame, Alexander would be inducted into Cooperstown and is widely considered to be one of the absolute best pitchers to ever play the game. If only Philly had kept him….sigh.