15 worst Chicago Cubs free agent signings in franchise history
1. Milton Bradley - 3 Years, $30 Million (2009)
Sure, Heyward was a major disappointment and drew the ire of fans for years - but at least he was a decent human being who provided at least some value, namely with his glove. The same cannot be said for the man who takes top billing on this list: disgraced outfielder Milton Bradley.
From the start, this marriage was doomed. By early summer, there was drama between Bradley and fans, the team's manager Lou Piniella and umpires around the league. That was just a sign of things to come. The outfielder put the organization itself and the media on blast in an interview in September and GM Jim Hendry suspended him for the rest of the season.
He never again played another game in a Cubs uniform. Chicago traded Bradley to Seattle that December after he slashed .257/.378/.397 in 124 games. The Mariners sent back right-hander Carlos Silva and cash in the deal, but it's safe to say that, no matter what, this deal was a complete and total failure by the organization and its biggest miss as far a free agency goes.