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First off, the cartoon is stupid and inaccurate. The bill was the work of the legislature and the executive, and of many, not one. It's associated with Obama, though, so to me the cartoon does have overtones of race and assassination. It draws from white petit-bourgeois resentment and complacency. To put it another way, it's as stupid as you would expect a Post cartoon to be.
Yes, Bush was portrayed as a monkey, but he's white, so it's not the same. Bush's portrayal was an extreme form of caricature, which riffed off Bush's physical features. This cartoon makes the link to Obama, but does it surreptiously and with plausible deniability, which makes it cowardly on top of everything else.
I wouldn't be surprised if the editor considered the racist angle and thought "free publiciity!"
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