In July of 2008, in the heat of Barack Obama’s first presidential race, The New Yorker issued a cover with an image titled “The Politics of Fear,” better known today as “the Obama fist-bump New Yorker cover.” In the drawing Obama appears strong jawed, decked in a turban and religious robes. He is pounding the hand of Michelle, who tops her baggy military fatigues and sprawling afro with a winsome grin.

The outrage was immediate. A spokesperson for the Obama campaign called the cover “tasteless and offensive.” Hundreds of readers threatened to cancel their New Yorker subscriptions. “The fact is, it’s not a satire about Obama—it’s a satire about the distortions and misconceptions and prejudices about Obama,” editor David Remnick told The Huffington Post in the image’s aftermath, explaining he hadn’t run the cover to evoke controversy but because he “thought it had something to say.”

This week, another image spawned a similar round of outrage, as the nagging scold of the internet weighed in on the New York Times Magazine’s latest cover—a floating image of Hillary Clinton’s disembodied head superimposed on a moon (it’s underscored by the title “Planet Hillary”). Detractors have been calling the cover sexist, offensive, and just plain ugly. In less than 24 hours in public, Hillary’s planet head has developed its own gravitational pull, satirized and photoshopped into further distortion, added to the cover of the children’s book Goodnight Moon and plastered like a spinning basketball into Barack Obama’s hand.

The Times Magazine internal blog covers none of the controversy over Clinton’s ugliness—nor the potential misogynistic overtones of the image—in a ‘making of’ post on its 6th floor blog. Editors there focused instead on the idea’s genesis, which came from the 1902 silent film Le Voyage Dans la Lune.

The lack of response to an onslaught of criticism raises a larger question: Did the Times Magazine editors know that their image was bizarre (and potentially offensive)? And if so, why did they release it? (Times Magazine design director Arem Duplessis didn’t return a request for comment by deadline.) But Steven Heller, a former NYT art director, says that, when brainstorming ideas, time-strapped compromises can supersede aesthetics.

“I think you get carried away with the idea, or you have to fill up space,” says Heller, who spent 30 years with the Book Review. Negotiating the visions of editors, creative directors and artists requires compromises that can often dilute good ideas according to Heller. “When I was at the Times, I had my share of things that went bad, and it was always because of expedience,” he says, “or I had convinced myself that it was brilliant and it wasn’t.”

Navigating the public’s response is more difficult when designing art for a news magazine, where tying art to a news cycle means a creative team might have less than a week to develop the image.

“It’s really seat-of-your-pants stuff, where you’re just looking for an arresting image that will draw the readers into the story,” says Robert Priest, creative director of Priest + Grace the design firm that produces the covers of Newsweek’s digital edition. Priest has taken to using graphics rather than the safety of the traditional news photograph. “We’re trying to do something that stretches the readers a bit—to view them as intelligent people who will get something that’s a little bit more subtle.”

As the fist-bump cover demonstrates, subtlety (or irony) doesn’t always translate. But that doesn’t mean, ultimately, that integrity can’t rise from the ashes of a whole lot of hoopla. The most iconic magazine covers are the often the ones that generated the most controversy when they originally ran. Like George Lois’s 1968 Esquire cover, which portrayed Mohammed Ali as St. Sebastian, pierced by arrows and bleeding. At the time, religious groups accused the magazine of heresy for using Christian imagery on the Muslim (and possibly draft-dodging) Ali. Years later, the Associated Press called the photograph an image “so powerful that some people of a certain age remember where they were when they saw it for the first time.”

Alexis Sobel Fitts is an assistant editor at CJR. Follow her on Twitter at @fittsofalexis.