Looking at 4 of the worst free agent contracts in Chicago Cubs history

4 of the worst free agent contracts in Chicago Cubs history: Milton Bradley

Woo, boy. Milton Bradley. What can I say that hasn’t already been repeated ad nauseam over the years? I mean, if nothing else, he certainly lived up to his reputation. The only problem being his reputation was far from sterling even at the time of the signing.

Chicago signed Bradley to a three-year, $30 million contract in January of 2009, looking to add a new look to a lineup that was dominated by right-handed hitters. As far as the numbers go, he was exactly league average for the Cubs – but there was so much unrelated to his on-field performance that played into this falling to pieces quickly, it’s unreal.

He made some really lackadaisical mistakes during his brief stop on the North Side, clashed with manager Lou Piniella and ultimately decided to put the organization on blast in a newspaper interview, commenting, ” you understand why they haven’t won in 100 years here.”

That got him suspended for the rest of the 2009 season and Jim Henry sent him packing in a trade with the Mariners that netted Carlos Silva, who had a solid final year in the bigs with the Cubs in 2010, going 10-6 with a 3.75 FIP and 100 ERA+.