Michael Dukakis was doing well in the polls in the late summer of 1988. Comfortably ahead of George Bush and basking in that post-convention afterglow. Then somebody in his campaign had the idea that what they needed to really put him over the top was a butch image. Something that would head off any claims that he was 'soft on defense'. So the campaign packed up the wagons and headed to Michigan where MD donned some standard issue tank wear (including a helmet with Princess Leia ear buns) and was photographed riding around conquering the General Dynamics parking lot.

To say that the resulting image backfired would be an incredible understatement. The hooting and hollering started almost immediately though nobody could quite put a finger on exactly what there was about the image that made it so cringe worthy. Dukakis was an army vet after all and had served his country honorably. Personally I think it was the helmet.

"Help me Obi Wan. You're my only hope!"