1. The Red Sox Trade Babe Ruth

Dumbass Move By: Harry Frazee and the Boston Red Sox
Date: 1/3/1920
Babe Ruth wanted a raise. That's all. The Red Sox refused to give him what he was asking for ($20,000), so Boston gave Ruth to the Yankees for $125,000. We all how that turned out, right? *cough Curse cough* 86-year championship drought x losing arguably the best baseball player of all time = Dumbest front office move of all time.