The problem with Juan Pierre was that the Cubs traded three pitching prospects for him, all of whom made the Big Leagues, and one of whom, Ricky Nolasco, ended up having a pretty decent career. Trading all that for one year of Juan Pierre was the height of stupidity. Pierre came in and did exactly what Juan Pierre does for his one year and then walked in free agency. It was the 2nd most emblematic transaction in the Hendry era. #1 was the sequence of transactions leading up to the 2009 season that essentially exchanged Felix Pie, Ronny Cedeno, and Michael Wuertz for Joey Gaithwright, Aaron Miles, and Aaron Heilman. Basically replacing some young, cheap players with older, more expensive, worse players with fewer years of team control.