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The Pittsburgh Pirates Passed on Clayton Kershaw in 2006

PITTSBURGH, PA - SEPTEMBER 06: A general view of the field in the fifth inning during the game between the Pittsburgh Pirates and the Cincinnati Reds at PNC Park on September 6, 2020 in Pittsburgh, Pennsylvania. (Photo by Justin Berl/Getty Images)

The Pittsburgh Pirates have had their fair share of problems drafting and developing players. This was especially true back during the early 2000s.

The Pittsburgh Pirates are not a very good team right now. This past season was a tough year, the team finished with the worst record in the league, and they have been trending in this direction since the 2016 season.