Last week I wrote about the five best off-season transactions the Yankees had pulled off over the last quarter century. Now it’s time to take a look at the five worst transactions during the same hot stove period. Oh, and sorry Seinfeld fans…the Jay Buhner for Ken Phelps trade took place in 1988, outside our time frame.
5. Andy Pettitte: The blame for this situation doesn’t reside solely with the Yankees, since we don’t know all of the player’s intentions, but the team never should have let Pettitte walk following the 2003 season.