President Obama bets the chalk. Every March, in what has become a public relations ritual, Mr. Obama releases his National Collegiate Athletic Association tournament brackets, and, every March, he—like the rest of America—fails to complete a perfect bracket. This failure, though, does not bother me (in fact, Mr. Obama identified the winning Tar Heels in 2009, in a March of his happier salad days, with an extra ten-plus percent of Americans’ approval). But the chalk—the chalk gets to me.

“Betting the chalk” is a vestige from pre-electronic gambling, which refers to heavily relying on favorites—so called because, as more and more money poured in behind the favorite, chalkboard listings required constant updates. Unlike the case for most betting scenarios, in the standard March Madness pool (albeit some allot extra points to upset picks), only correct answers matter. So betting the chalk has the highest odds of success, and also the highest odds of being replicated, which in the average year’s large office pool leaves a chalk-better with a respectable but unimpressive finish. Betting the chalk is cautious. It is prudent but restricted. Both above-average and mediocre. You might almost call it conservative.

That term rarely finds its way to President Obama, but it really does fit his bracketology. Of twelve prior Final Four selections as president, he has chosen nine number one seeds and, in a bold departure, three number two teams. (It turns out, only about 42 percent of the correct twelve were ones or twos, but then again, I’m not here to grade performance; mine is much worse.) This year’s bracket is no less cautious. It sports two number one teams in the final four, and two twos—but those second-seeds are matched up opposite the weakest pair of the top four, Syracuse and Michigan State. The lone long-shot in the Sweet Sixteen is North Carolina State—but, despite the 11-seed branding, Las Vegas favored the Wolfpack to win their first game over number six San Diego State. Aside from a few less-than-daring ten-over-seven selections, Mr. Obama’s only other upset of note comes from number 12 Virginia Commonwealth. But the twelve-seed upset is de rigueur; a twelve has undone a five-seed in all but three prior tournaments—and what better a choice than last year’s glass-slippered darlings, VCU? One might even accuse the Obama bracket as politically influenced (three of four Final Four teams—University of North Carolina, Ohio State, and Missouri—from potential 2012 battlegrounds) if it weren’t for the uniform sterility those picks embody. That is, if the chalk weren’t flying everywhere.

Mr. Obama’s brackets say something about him. That conjecture might feel unfair, but he is the POTUS—over-scrutiny is a price he pays. At least, those cautious picks fit a broader narrative. The president, in many respects, has had a cautious tenure (and his campaign, like it or not—with its patented pay-your-fair-share and say-no-to-the-party-of-no approach—seems similarly situated). After a predictable early-on push for campaign promises, Mr. Obama has followed, in many respects the path of least resistance. On foreign policy and terrorism he has gestured to the left with some war-ending grandiosity but has dithered in Afghanistan, unwilling to fully leave or to fully stay, and has dealt with captured terrorists as a Republican might. On the economic frontier, his debt-ceiling kerfuffle ended in anti-climax—no new revenues, no substantive cuts. The list is longer, but, in fairness, there have been obstacles. Yet Steve Jobs’ words must speak for many on the left: “The president is very smart. But he kept explaining to us reasons why things can’t get done. It infuriates me.”

Still, I must confess, my view is biased: I am no Obama-enthusiast. But although I sit on the spectrum’s conservative half, that doesn’t mean I embrace caution, at least not political caution (maybe I am living through America vicariously; I’ll talk that one over with my therapist). It does mean I am faced with a probable nominee who relishes that embrace. An odds-on Republican who clings to an opinion poll the way pundits accuse his counterpart of clinging to a teleprompter, a man made by the free market who has blared out anti-market trade positions, a politician whose healthcare proposals morph as one voting pool supplants another, a candidate with a low-change tax policy, who opted for a slightly-more-change tax policy when pushed. A man “not plugged-in enough,” in his words, even to complete a March Madness bracket (lest he pick incorrectly). All of that well-publicized caution triggers a guttural frustration in me—playing not to lose, as they say; not playing to win.

Most people, my economics textbook tells me, are risk-averse: They gain less happiness from each marginal bit of something good—and thus more unhappiness from each marginal piece that disappears. That might mean we should welcome a cautious president—and I certainly don’t want a firebrand. But maybe, I want a president with conviction, with a vision for the country, not a piecemealed rearguard scheme. Maybe I want a Lincoln or a Reagan or (and this is conservative anathema) a Franklin Delano Roosevelt. Sure, betting the chalk puts you right up near the top. But maybe I want to win.

Brian L. Cronin ’15, a Crimson editorial writer, lives in Wigglesworth Hall.