Bad trades in history?
June 15, 1964.
The Cubs give away a skinny outfielder to the Cardinals for Ernie Broglio. Some kid named Brock.
One more little thread highjack.
I'll see that trade and raise you a Mathewson-Rusie trade. The New York Giants trades Amos Rusie to the Cincinnati Reds for the then-unknown Christy Mathewson. Rusie only pitched in three games with Reds, with no victories while Christy Mathewson went on to win 373 games (including 80 shutouts) for the Giants and was one of the original five members of the Hall of Fame (with Ruth, Cobb, Johnson, and Wagner).