Back in July, 2008, after Barack Obama had wrapped up the Democratic nomination but before the party convention, the New Yorker published its infamous “Politics of Fear” cover, intended to satirize the worst beliefs about the Obamas circulating in various right-wing media. Despite the stated ironic and satirical intentions of the cartoonist and the editor of the New Yorker, many people considered this image to be at best a failed attempt at satire, and at worst, a wildly offensive and racist caricature. While my primary scholarly interest in this ambiguously satirical artifact is what it and the discourse surrounding it tells us about how irony and satire work, in this post, I am interested in revisiting the attendant controversy and how it reflects on progressive media criticism in the blogosphere. Is the certainty with which many presumably progressive individuals asserted that “most Americans” simply wouldn’t and couldn’t get the joke a symptom of elitist “blue-state” attitudes towards benighted “red-staters”? Was the fear that right-wing media would be able to use this image to prove that the Obamas are terrorists or that this image revealed the New Yorker’s true conservative colors (or its fealty to Hillary Clinton and/or AIPAC) evidence of progressive paranoia that conservatives had not been winning elections because they were persuasive but because they controlled the media? Could the negative reaction to this cartoon been in part the result of an unrealistic hero worship of Obama, forbidding any humor at his expense? I ask these questions not to dismiss progressive criticisms of this New Yorker cover in particular (indeed I find many thoughtful arguments on the nature of irony and satire in this controversy) nor of U.S. political culture in general. However, with the benefit of hindsight following an election where Obama won 53% of the popular vote and 365 electoral votes, including those of Southern states Virginia and North Carolina, it seems that perhaps some of the reaction reveals a progressive blogosphere blind to its own narrow-mindedness toward certain out-groups, sometimes prone to literalism, and needlessly pessimistic about its ability to win elections.