The Chicago Cipher

Illustration by Demetrios Psillos

We had been on the phone for barely five minutes—talking about another subject entirely, as it happened—when the political consultant Mark McKinnon started spinning an elaborate and alluring fantasy about, what else, Barack Obama and the presidency. “There’s this great documentary out right now about Barry Goldwater,” said McKinnon, who served until recently as media guru to George W. Bush and currently advises John McCain. “And it reveals that Goldwater and John F. Kennedy were having conversations about how, if they were the nominees in 1964, they were going to jump on a plane and campaign together around the country. Which is a really interesting idea, and the sort of thing you could see Obama and McCain doing. I mean, wouldn’t that be great?”

Now, McKinnon isn’t exactly your typical professional partisan: Before taking up with Bush in 1998, he was a lifelong Democrat. And yet in many quarters in Washington and beyond, his reverie—not in its quirky specifics but in its expectant, roseate spirit—is the political dream du jour. The dream of Obama’s not simply running but transforming our politics. Indeed, transforming the country.

Before all that could happen, of course, Obama would have to win the Democratic nomination. And here the dream is equally seductive. Among many serious Democrats, the consensus is that if Obama runs—an eventuality everyone now considers a foregone conclusion—the contest immediately becomes a two-horse race between him and Hillary Clinton. Slate editor-in-chief Jacob Weisberg goes further, contending that “Obama, not Hillary, [would] be the de facto Democratic front-runner.” And Markos Moulitsas, the commissar of the liberal blog Daily Kos, goes further still: “If Obama runs, he wins.”

Let me say that I find Obama an intriguing and compelling character: obviously talented, often inspiring, the possessor of nearly infinite potential. I have no doubt that he shouldn’t wait—that the time for him to run is now. And I’m prepared to believe that he would make a stronger Democratic standard-bearer than Clinton or any of the other wannabes nervously awaiting his decision. But let me also say that Weisberg, Kos, and many other Obamamaniacs must be smoking something (and, whatever it is, I’d like a taste). For all his promise, Obama is basically an empty vessel, with vulnerabilities that have been obscured by his blinding, meteoric ascent. And though it’s not impossible for him to win the Democratic nomination, the road to that destination will be rougher than his adherents admit—or, quite possibly, than Obama himself imagines.

Two weeks back, when Obama rolled into town to address a charity dinner for kids in poverty (and squeeze in a few meetings with big-dollar donors such as George Soros), I hustled over to the Mandarin Oriental to catch his act. As a speaker, Obama is cool in the strictest sense, his tone even and conversational, his gestures spare and deliberate. He began his talk with a story about Robert F. Kennedy’s trip to the Mississippi Delta in 1967. Visiting one tar-paper shack, Kennedy encountered a child with a distended belly and hollow eyes. “At that point, Bobby Kennedy begins to cry,” Obama said, “and he asks, ‘How can a country like this allow it?’ How can a country like this allow it?”

Obama’s affinity for RFK is pronounced and unsurprising. In the fall of 2005, he recounted that same story in the keynote he delivered at the Robert F. Kennedy Human Rights Award Ceremony—a speech in which he identified the qualities that have made the ghost of RFK enduring. Charisma and eloquence. Youth and energy. “An idealism not based in rigid ideology.” An outlook “hard to place … into any of the categories that so often constrain us politically.” The very set of qualities, that is, that many people now discern in Obama—and that he so clearly aims to project.

Yet the differences between Obama and RFK are many, beginning with the length and depth of their résumés when their eyes turned toward the White House. By 1968, Kennedy had not only served three years as a senator from New York but three as U.S. Attorney General. He’d been a central player in shaping his brother’s foreign policy and had spent much of the decade knee-deep in the civil-rights movement. Obama’s stint in the Illinois State Senate pales by comparison.

God knows the last thing I’d argue is that Obama ought to pad his CV by loitering for years in the Senate, an institution that prepares one for little besides the exercise of pomposity. But, substantively speaking, Obama hasn’t even made the most of his brief time there. The legislation he has offered has been uniformly mundane, marginal, and provincial—securing additional funding for veterans, to cite but one example.

Obama’s response to such criticism is to point out that he’s been constrained by his status and circumstances: a freshman senator in the minority party. “I’ve got a lot of clout,” he jokes. “I went from 99th to 98th in seniority this year.”

A clever line, sure, but patently bogus—for, given the extent of Obama’s celebrity, he’s hardly an ordinary backbencher. Yet how many times has he used his megaphone to advance a bold initiative or champion a controversial cause? Zero. Instead, Obama has tempered his once-fiery stances on such issues as Iraq and health care; his proposals on alternative energy and global warming are weak beer compared with those of, say, Al Gore. He seems a man laboring to stay something of a cipher—a strategy no less calculated than Hillary’s conspicuous lunges to the center or McCain’s lurches to the right.

Obama seems to be laboring to remain something of a cipher—a strategy no less calculated than Clinton’s or McCain’s.

Plainly, this strategy has worked for Obama so far. The excitement he’s generated isn’t issue-based: It’s stylistic. His popularity is rooted in his calm, consensus-seeking, deliberative demeanor and in his calls to common purpose. The question, however, is how well this brand of popularity will hold up when voters learn more about him—from trivial things, such as the fact that he’s a smoker, to his fairly conventional liberal policy positions—in the course of a primary campaign. In Iowa, New Hampshire, and other key early states, his leading rivals (Clinton, John Edwards, John Kerry, perhaps Gore) are known commodities, whose supporters are well aware of who they are, warts and all. Nothing remotely similar can be said right now of Obama.

Nor is the process likely to be forgiving of his screwups—the gaffes, the ill-timed revelations, the poorly vetted contributors.

And let’s not forget, Obama will enter the race a remarkably untested candidate by almost any standard. None of his races for State Senate were competitive—he ran in an effectively all-blue district. His election to the U.S. Senate in 2004 came after Jack Ryan, his Republican opponent, quit the contest after being ensnared in a sex scandal and was replaced by (ahem) Alan Keyes. In his new book, The Audacity of Hope, Obama notes that neither Ryan nor Keyes ran a single negative TV ad against him.

All of which suggests why, for all the (reasonable) concerns about her prospects in a general election, Hillary Clinton remains—and will continue to remain, regardless of Obama’s entry—the prohibitive favorite to win the Democratic nomination. She has the money. She has the résumé. She has the policy chops, the shrewdest political adviser on the planet (i.e., her husband), and the unwavering allegiance of a substantial bloc of her party’s primary voters. A recent Fox News poll put her support among Democrats at 33 percent—compared with just 12 percent for Obama, 11 percent for Gore, and 8 percent for Edwards. And in a head-to-head matchup, Clinton beat Obama by a fat margin of 52 to 30.

What Obama has going for him that Hillary does not is that people genuinely like him. The power of personality in politics cannot be overstated. Duh. And neither can the appeal of a leader who promises to deliver us from the tired and tiresome contours—the moralism, narcissism, condescension, and histrionics—of civic discourse as practiced by the baby-boom generation. The essence of Obama’s pitch is that it’s time to move past the old politics and that he’s the embodiment of the new. And after the scorched-earth tactics and wretched polarization of the Clinton-Bush years, anyone who dismisses the potency of that message hasn’t been paying attention.

It’s worth noting, though, that assaults on “old politics” have been tried before—most famously by Bobby Kennedy. It’s also worth noting that Kennedy’s campaign in 1968 demonstrated the limits of such a stratagem. One of the great and dogged myths of our recent political history—a myth propagated by that boomer cohort and one implicit in Bobby, Emilio Estevez’s current piece of cinematic hagiography—is that, if not for Sirhan Sirhan, Kennedy would have marched to the Democratic nomination and then to the presidency. Yet almost every serious scholar of 1968 holds a different view: The likeliest outcome was that RFK, for all the passion he inspired, was going to lose to Hubert Humphrey, old politics personified.

No one, obviously, can know for sure about that, just as no one can say with any certainty what 2008 holds for Obama. But, win or lose, Obama’s prospective candidacy has already changed the game. He’s already tested Hillary Clinton, and is making the rest of the field redefine themselves. But the bigger test will be for himself.


The Chicago Cipher