In purely baseball terms, the Milton Bradley signing didn’t hurt the Cubs nearly as much as is being reported. And signing him wasn’t the worst move of the season. Not benching him earlier or more frequently was not the worst move. Neither was the refusal to put him on the DL. This award goes solely to Milton Bradley himself.
The reason all the other baseball moves pale in comparison to Milton’s actions and attitudes is the simple fact that all the other moves could have worked out. Aaron Miles’s stats have never been as bad as they were this year. Milton’s numbers should have been better. The Cubs overall should have scored more runs. Relief pitchers can be unpredictable fellows, and the bullpen was far from being the biggest problem on this team. The one personnel move that had no chance of helping the Cubs immediately was the Mark DeRosa trade, securing its position as runner up.
But Milton turned on the fans early and often and withdrew from his teammates maybe as far back as spring training. He conducted himself like an angry child, not just in the heat of the moment but also in the daily grind of the season. That never works. Its effect on this Cubs team is often exaggerated, but the effect it had on Cubs fans is inarguable. He made this season suck more, and he alone is responsible for his actions. Awarding the WMotS to anyone else would fail to hold him accountable for his egregious conduct.
So, Milton, take this award and put it on your mantel*.
*and by on your mantel I mean up your self indulgent ass.