William, the duke of Normandy: 1048 to 1060
This was the most foolish, daring thing you could embark upon. Not only have you taken on a foe almost equal to yourself in military resources: you have made the king of all Frenchmen a victim of your blatant aggressions and ambition: when king Henry calls on Anjou, Maine, Brittany, Boulogne, Ponthieu, AND Flanders, they all send contingents to the aid of their king. Your stupid grasp of strategy has never manifested itself until now: you have merely been lucky. When you are taken captive or killed in battle, nobody mourns your loss, and history only remembers you as "William the (poor stupid) Bastard."