What goes on under the hood at Wolfram Alpha is a mystery to my simple mind, but after seeing the results of this search, I hope whatever it is gets an overhaul quickly. Updated.
You see, tipster Jon-Paul snagged this screen shot of his search for "dumb" (which I cropped to cut out his desktop, fyi).
I then did a search of my own to dismiss any Photoshopping concerns. The results were the same in each case: Racist synonym trees that associated the word dumb with black.
What the heck, Wolfram?
Update: Ah, a response from Wolfram Alpha on the issue. Seems that, as the synonyms get further and further away from one another, things get more vague (Wolfram Alpha gives a much better explainer than that—check it out).
The Wolfram Alpha blog is asking the community for suggestions on how to make obscure connections like this one more easily understandable for the masses. [Wolfram Alpha - Thanks, John-Paul]