In April of 2011, it was discovered that Marilyn Davenport, a prominent Republican organizer in Orange County, Florida, had circulated an email that depicted President Obama as a baby ape posed with two ape parents; the caption read “Now you know why no birth certificate.” While there was a considerable outcry from offended parties—and considerable pushback from those who felt like Blacks are just too sensitive for words and can’t ever just take a joke and, thus, are the real reason this country will never get past race—there was also little surprise over Davenport’s picture. The sky is blue. Water is wet. Conservatives often harbor deep-seeded racism. You’d have to be a resident of Mars to find anything shocking about that incident.

Fast forward to this week. Dan Amira, an associate editor for New York, published “Obama Gay Marriage Evolution: Day 468.” The title is not misleading: it’s a quick aggregated piece about the president’s developing stance on marriage equality, which has changed a bit since he entered office 468 days ago. Amira, like many of us, is ready for POTUS to slap a rainbow flag across the White House doors, give a middle finger to conservative opponents and finally make marriage (or at least civil partnership) an option for all Americans. Maybe in his second term.

Yet it isn’t Amira’s thoughts on President Obama’s politics that are drawing ire. It’s the image used to accompany the story (pictured above): a riff on the classic Darwin’s evolution of man chart that depicts the president as a knuckle-dragging primate that becomes a bipedal man carrying a rainbow flag. Get it? Evolution used to illustrate…evolution. They so clever at the New York Magazine! If this were 8th grade, someone would receive a gold star in the column marked “creativity.” Alas, the lack of a racial sensitivity grading scale would likely prevent Amira and his illustrator from receiving the critique they deserve (if there was one, perhaps this gaffe wouldv’e never happened).

This isn’t a matter of being failing to be “politically correct”— a term that sounds friendlier than it is, as it is often code for ‘keep the racist/sexist/homophobic/abelist stuff to yourself in public, because people get sensitive about the truth!’ This isn’t a matter of being respectful in the ways in which the leader of the free world is depicted; as it was often said last year, President George “Katrina Who” Bush was depicted as a monkey (and worse) plenty of times during his time in office. And President Obama has been cast as Hitler more times than any German actor, so the monkey pics aren’t really the worst offense thrown his way.

The problem here is the fact that YOU CAN’T CALL BLACK PEOPLE MONKEYS ALL WILLY NILLY! It harkens back to years of racist pseudo-science and maltreatment. Remember the whole “three fifths of a human being” thing? No? White privilege sure does make it easy to forget.

Marilyn Davenport’s monkey business was par for the course, as she is a member of a group that has made race baiting (and race hating) its calling card. Amira, however, is a liberal. He’s championing for the humanity of a marginalized group who have been denied the same rights and privileges as other citizens. Is liberal racism new? No, of course not. But it can be a particularly bitter pill to swallow. These are, more often than not, our ideological allies. These are the ones who claim to imagine a world of equality. So, how is it too much to ask that they would be sensitive to the racism we’ve endured since before the first Africans arrived on these shores?

Let’s not ignore the great forehead-slapping moment that comes when you realize that this unfortunate artwork was used to illustrate a piece championing gay rights and how often those LGBT persons are unjustly compared to/put at odds against Blacks, giving the “Invisible Man” treatment to those brothers and sisters who wear both marginalized hats. Bad move, playboy. Now we’ll be subject to the requisite “See! The Gay Agenda doesn’t care about Black people” complaints once this story hits MySpace. And we JUST had to deal with that with the Roland Martin/GLAAD fiasco. Sigh.

Amira’s piece (and his rebuff of Keli Goff’s inquiries about the picture on Twitter) isn’t the most egregious act of casual racism we’ve seen even in the past month. It’s just yet another reminder that White folks of all political schools of thought are lacking compassion and context when it comes to race. And so long as America is about as post-racial as Maury is post-DNA testing, this is going to continue to be problem.