Obama's Insecure Slip

What led the president to wade into L’Affaire Gates? He thought he’d blown it with America on health care.

Jim Young / Reuters

Read other takes on Gates' arrest from Daily Beast writers.

Obama’s unaccustomed carelessness in jumping on a racial landmine at the end of his health care press conference illustrates two things. First, his vanity as a performer. And second, his insecurity about his health care arguments.

The president, after a wordy, wonky, depressingly unconvincing briefing—one that he is pro enough to sense failed to make the sale to the press—eagerly took the question from Chicago reporter Lynn Sweet about the Henry Louis Gates affair. Obama saw it as a chance to be funny, to be real, to be his charming self—and to win back the room.

Obama saw the Gates affair as a chance to be funny, to be real, to be his charming self—and to win back the room.

“The guy,” he said, referring to his friend Gates, forgot his keys, jimmied his way to get into the house. There was a report called into the police station that there might be a burglary taking place. So far, so good, right? I mean, if I was trying to jigger into—well, I guess this is my house now, so [ laughter] it probably wouldn't happen. [ Chuckling.] But let's say my old house in Chicago. [ laughter] Here I'd get shot. [ Laughter.] But so far so good.

So far so dangerous. As every late-night comedy host knows, it’s when the audience is with you, when the guest feels that heady rush of positive response from the crowd, that the moment overwhelms the outcome. Obama had fallen into this trap once before—unsurprisingly, on The Tonight Show, when, rising once again to the chance to show his humor (and human) self-deprecation, he mocked his own bowling skills as being like “the Special Olympics or something.” And all hell broke loose.

It was an index of how badly Obama felt he had fared during his lackluster presentation of health care priorities that he did not instantly pull himself up after saying, “The Cambridge police acted stupidly in arresting somebody when there was already proof that they were in their own home.”

Sitting mesmerized on a Manhattan sofa at a small dinner for a foreign diplomat hosted by a television executive, all six of us at once stiffened and groaned when that radioactive word—“ stupidly”—came spilling out of Obama’s mouth (a mirror image, no doubt, of whatever greenroom sofa seated his advisers David Axelrod and Robert Gibbs).

It was baffling enough that one so practiced in media manipulation had suddenly ensured that the next day’s radio and TV talkathons would ignore his health care agenda and focus on the much more entertaining replays of his jokey, rueful, entirely inappropriate weigh-in on a local incident about which he had blithely admitted he did not know all the facts. But the way he sailed on unhesitatingly into a glib riff about racial profiling showed that Obama had, as they say in the U.K., temporarily lost the plot.

The question is, why? This president is not used to a fight in which his eloquence seems powerless to sweep everything before it. My sense is that Obama is pretty much at sea on this one. Health care needs some kind of impossibly napoleonic fiat to get the job done—or, at least, an LBJ-ish mastery of the back rooms, a veteran’s grasp of how you twist arms and offer inducements to guide the process to the result you want. Instead, he’s floundering in a political swamp where everything gets decided by collectives of compromising mediocrities. Plus, Obama just loves those teachable moments and couldn’t resist the urge to bestow one.

Obama wanted to seem as cooperative with Congress as Hillary wasn’t back in 1993. But now it all feels as foggy as pea soup and no one is happy. Did he stumble so badly because he is feeling so vexed and depressed over the way what should be his signature accomplishment is slipping away from him?

Tina Brown is the founder and editor-in-chief of The Daily Beast. She is the author of the 2007 New York Times best seller The Diana Chronicles. Brown is the former editor of Tatler, Vanity Fair, The New Yorker, and Talk magazines and host of CNBC's Topic A with Tina Brown.