I saw a reference to a story in another favorite site (Consumerist.com) that made me look back a few months. Apparently WalMart has been selling a t-shirt with a odd logo of a skull and “Since 1978″ below it. What they didn’t realize was that the insignia used in WWII for the Nazi 3rd SS Division Totenkopf.
I guess they apologized for it and stated that it would be removed from all stores. But supposedly it’s still available 10 weeks after the fact.

This definitely ranks in the annuls of “stupidest moments of graphic design” in my opinion – and all at the unknowing hands of WalMart.