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It is a miserable November day and Gregor Robertson is late for lunch. Outside, Vancouver goes about its business under a gloomy grey canopy. On the sidewalks, people bow their heads against the wind and rain, struggling to keep the ribs of their umbrellas from turning inside out.

Out of the darkness emerges a man on a bike. He is no courier forced by the nature of his occupation to be out in such a squall. He is wearing suit pants and dress shoes. As he takes off his helmet his sharp features prompt double-takes among those walking by. His face looks familiar – and it should. He's the town's mayor after all.

"You ride in this stuff?" I ask.

"Yes, most of the time," he says after taking a seat in the restaurant. "It's just how I get around."

Say what you will about Gregor Robertson, but at least he puts his pedals where his mouth is. As the architect of the most contentious bike lane project in the country, it helps him avoid looking like a hypocrite. It also ensures that he stays in fighting trim. The job may have given him a few grey hairs, but he still looks much younger than 47.

It's been one year since the mayor's re-election. And so far his second term has been a much smoother ride than his first. I don't cover the mayor on a day-to-day basis, but from a distance, at least, he seems to be wearing the job better. What is it the wise man said? Experience is a hard teacher because she gives the test first and the lesson afterward.

Mr. Robertson seems to have emerged from his first term with a newfound confidence.

He's like the novice sailor who survives a wretched and terrifying bout of weather.

On the other side of that event he is a completely different mariner, one who is more cool and assured under pressure.

The mayor took office in 2008 when the effects of the financial crisis had really taken hold. It was largely responsible for the mess that unfolded at the Olympic Village, one of the biggest financial dilemmas the city has ever confronted. Then there was Snowmaggedon – a freak snowstorm that virtually paralyzed the city and endangered the lives of dozens of people living on the street. The Olympics themselves were a wonderful reprieve, but a year later Mr. Robertson was dealing with the biggest riot in the city's history. And in the midst of his campaign for a second term, Occupy protesters took over the grounds of the Vancouver Art Gallery. Other than that, Mrs. Lincoln, how was the play?

You can certainly question how the mayor handled some of these matters. We still don't know how much money the city will lose on the Olympic Village, but it would have lost less if it had sold the units set aside for social housing. That was an ideological decision on the part of the mayor's Vision Vancouver government I felt was difficult to justify.

He should have asked harder questions of his police chief concerning the city's preparedness for Game 7 of the 2011 Stanley Cup final. There was too much blind trust. On the other hand, the patience Mr. Robertson showed during the Occupy demonstration was commendable. It likely helped prevent a bloody showdown with police and allowed the encampment to be taken down peacefully.

"It was an incredibly intense period just in terms of everything that got thrown at us," says Mr. Robertson of his first term. "I appreciate having a little less stress in the day-to-day. We haven't had to be so reactive. We can be more pro-active instead."

You can roll your eyes at the mayor's pledge to end homelessness by 2015 – many have. We know it's not going to happen and never was. But with the province's assistance, he's helped get a lot of people off the street. It's been expensive, but it's what he promised and he should be applauded for it. Just as he vowed to make Vancouver the greenest city in the world – whatever that means.

I'm not sure who judges such things and what criteria they use. But give Mr. Robertson credit for making his city more liveable and for not caving in to the car lobby and its empty warnings that bike lanes would signal the end of commerce in the city as we know it. It did nothing of the sort. It just made the city a more desirable place to live.

He's helped lure green jobs to Vancouver. It's also become an attractive destination for entrepreneurs under his watch. Sam Sullivan deserves credit for envisaging an eco-friendly densification of Vancouver, but Mr. Robertson gets kudos for actually making it happen, perhaps at a faster rate than some are comfortable with. He's also tried to make the city more affordable in the process – although the jury is still very much out on how that endeavour ultimately fares.

Gregor Robertson is putting an indelible mark on Vancouver, but you may not notice it for years to come. On balance, he has done far more good than bad. The political opposition in the city has effectively disappeared during his reign – a development from which he's unquestionably benefited. It's difficult to imagine anyone seriously challenging the man in the near term – which is perhaps why he's already announcing that he'll be seeking a third mandate.

"I love my job," he says. "Plus I still have a few things on my bucket list for the city I need to get done."

And with that, the mayor hops on his bike, straps on his helmet and takes off down the street – in the pouring rain.