The infamous Willie Horton Ad that did much to bury Michael Dukakis in his race against George H W Bush. Yep, it is the one that basically says "vote for my opponent if you want a black man with a beard to come round and rape you." This ad was certainly ugly; the terrible thing is, it was also very effective.
Interestingly, Lee Atwater - one of the figures behind this ad - later apologised for all his negative campaigning on his deathbed. Which is all very well, but the charge of too little, too late could really stick in this case.
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