Worst Box covers
If you are going to have your best covers, the corollary is the worst covers. These are all games I owned or still own.
5 Europa series 2nd edition covers - ex. The Fall of France - I think I can find France on a map of Europe without a guide.
Fall of France - box cover
4 Battle Cry - 1999 edition a great C&C game. However, you are being charged by 4 reenactors. Gee wiz guys I have better kit.
Battle Cry - box cover
3 Friedrich - great game and the components are good but that cover. Looks like Fredrick is having a paranoid delusion. Of course if they are really out to get you, you are not paranoid or having a delusion.
Friedrich - box cover
2 Napoleon at bay - AH edition - it speaks for itself.
Napoleon at Bay - box cover
1 A House Divided 3rd edition. Nothing speaks of historicity better than the 18 stripe US National flag and a Prussian officer leading the union troops.
A House Divided - box cover
Honorable mention
Use to have the one Judd mentioned.
War without Mercy - 1st edition. The Nazi wolf being bayoneted. Honorable Soviet propaganda art, pretty weird for a cover though.
War without Mercy - box cover