This is just the sort of thing that Obama cannot afford, and which he would be wise to disown immediately, but it ties into something I wrote earlier about the globo-man persona he and his admirers have been crafting for him during the campaign:

The other problem with this talk of Obama as a bridge-builder with the Islamic world is that people might take it rather too seriously and see him as being too close to the Islamic world.  The logic of “only Nixon could go to China” applies here as well.  Someone who is already seen, rightly or wrongly, as personally close to or understanding of the ‘other’ has much more difficulty engaging in the kinds of negotiations or contacts that Obama proposes to have. 

Instead of appearing to be too close or associated with the Islamic world, here there is a danger of getting a reputation for sympathy for “rogue” states, and for Cuba in particular.  Obama has gone out of his way to make clear that he is willing to negotiate with hostile and “rogue” regimes, which is, in principle, a reasonable and defensible position, and one where I happen to think Obama is right.  However, his early formulations of this position were clumsy and excessive, as I argued in the magazine last September:

Moving from Bush’s approach that disdains diplomacy as a sign of weakness, he proposes to make a travesty of diplomacy by conducting it cavalierly and without purpose.

Nonetheless, his sane willingness to ease travel restrictions to Cuba and his willingness to meet with leaders of Syria and Iran have been evidence that some small good might come from an Obama foreign policy, deeply flawed as it otherwise is.  However, this symbolic blunder at his Houston campaign office feeds into a narrative that Obama is not just taking different, defensible views on how the United States should conduct its foreign policy, but that he is, or at least members of his campaign are, somehow sympathetic to some of these regimes.  (To some extent, Obama’s campaign workers will be forgiven by many observers because Che chic is the sort of ignorant, fashionable “hero”-worship that rather a lot of young college lefties have engaged in at one time or another, and it will be treated as a sort of harmless stupidity.)  Of course, I don’t think Obama is sympathetic to the mindless Che admiration that evidently grips some of the people who work for him, nor has he shown himself to be in any way sympathetic to the Castro regime, and such views should not be imputed to him.  Even so, if symbolism feeds an already-existing assumption or perception about a candidate it will catch on and turn people against him (i.e., he wants to talk to Castro because he and his supporters are basically in agreement with the revolution).  At that point, earlier episodes, such as the ridiculous “flag pin controversy,” re-emerge in the news and take on new significance.