Adam Giambrone has the wrong hair to be mayor. Buzzed on the sides, a little longer on top. He goes to Connie Croce of His and Her Hair Place at Bloor and Dovercourt. A $15 job. Giambrone has been seeing Connie since he was five years old—he’s a loyal guy, and he likes his low-maintenance cut. But the look is a problem for his campaign, and his team is trying to persuade him to change it. When you’re running for mayor, you shouldn’t remind voters of a teen geek.

It’s a minor miracle that Giambrone, six years into office, continues to look boyish, when you consider how ruthlessly city hall sucks the sense and vigour out of its residents (David Miller appeared to double in age over his last term). Giambrone is 32, which makes him the youngest city councillor by seven years. Sitting in his city hall office, he leans back in his chair and stretches his hands behind his head like a high school teacher who wants to convince his students he’s a casual dude. He’s often asked if he’s old enough to run for mayor and betrays some impatience with the question (“It’s not relevant,” he says). Besides, he points out, Toronto has had two 30-something mayors, David Crombie and John Sewell. Sure, OK. But they were each well into their 30s when they were elected, and neither could pass for Doogie Howser.

Doogie couldn’t survive what Giambrone has been through. The TTC chair since 2006, he’s blamed for every late bus and rude driver. If there’s one thing everyone in this city agrees on, it’s that the TTC gets lousier every year. Our hate-on intensified during the subway stoppages and token shortage gaffe that marked the end of last year. Unlike his predecessor in the job, Howard Moscoe, Giambrone doesn’t tell his critics to stick it; he remains infuriatingly rational, placidly agreeing that the TTC isn’t perfect, then systematically describing every planned improvement. He knows the TTC inside out and takes pleasure in reciting minutiae from 1,000-page studies. That nerdiness, the patter of a bureaucrat, is easily mistaken for a blocked sympathy valve. But he’s not completely robotic; he’s a fierce debater in council chambers, and if you accuse him of not doing his homework, he’ll raise his voice and punctuate words with a jab of his finger.

So why is he running for mayor? He says, of course, that he wants to make this a better city. He also admits he wasn’t planning to go for it this time, that he’d expected Miller to stay in the race and win. Now he feels that he has no choice. He believes he’s the only truly lefty candidate (so far), and he’ll have the NDP vote locked up (he was the federal party’s president for five years, elected to the position at 24). Giambrone is even more idealistic (that youth thing again) than Miller, and like his mentor, he’s a wide-eyed follower of Jane Jacobs (posted above his desk is her line about cities being “fantastically dynamic places”). But his ties to Miller, who in the final years of his mayoralty is considered a milquetoast has-been, could be a bigger handicap than his TTC stewardship.