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He emerged on the civic political scene almost 10 years ago exactly, an improbably good-looking would-be mayor of Vancouver promising to end homelessness, make the city the greenest in the world—and bring in a “speculator’s tax” to curb the always festering problem of disappearing affordable housing.The first proved to be much tougher to wrestle to the ground than Gregor Robertson, one time organic-juice entrepreneur, and his team had imagined. Although the city made some Herculean efforts, pushing for a new kind of shelter that would be open all winter long (something the province has now instituted in other cities), fighting the province and various agencies to make sure that truly homeless people got housed in newly opening projects, the tide kept bringing in more homeless people all the time.The second “greenest city” goal brought in accolades from the environmentally minded around the world—but often criticism at home from those who griped persistently about the new green world of minimal natural gas, lots of bike lanes, and a tough building code.And the speculation tax. Well, that vanished quickly from Robertson’s campaign platform in the run-up to the 2008 election. It was pooh-poohed as too interventionist, too socialist, and he ditched it after a couple of public trial runs.Instead, as the housing market collapsed during the world-wide recession, he worked with developers in his first year to come up with one solution that focused instead on giving them plums if they would build rental housing. Vancouver has seen a success story on that front, with more purpose-built rental housing built in the last five years than the previous 30.But it wasn’t enough. As residential real-estate prices began to accelerate with the force of a rocket ship trying to break free of earth’s gravity, efforts that would have been praised in earlier eras came to seem inadequate, like trying to shoot that rocket ship down with bows and arrows. The mayor brought back the idea of the speculation tax in 2015, but it seemed too little, too late by then.The fury over that—along with bike lanes, natural-gas bans, and other sins—might have been tempered somewhat if the mayor had been a better salesman for what he was doing. But he wasn’t.He has always been a cool, reserved person, not one for indiscriminate schmoozing. He had the CEO persona: conversation was transactional, about getting things done, not about emitting sociability pheromones. I would hear stories from average residents, insulted that he had seemed to dismiss them or try to get away from them when they ran into him at public events. He hated public meetings and being grilled by increasingly hostile crowds.(One shining exception I saw to that was when he waded into the crowd of Marpole protesters objecting to the temporary housing for the homeless in their neighbourhood. Then, he seemed to relish engaging with them—perhaps because it allowed him to come across as a champion for the homeless in the face of the NIMBYs, a sweet spot for any politician.)He never liked reporters much and their questions. Even this week as he was announcing his future departure from office after 10 years, his interviews were often punctuated by long silences or unbearably painful, hesitant answers that seemed like they were being extracted by a dentist.The mayor was more confident and articulate when he had the floor—at council, at international meetings of green cities, in forums of the like-minded. But most people never saw that. Instead, what they mostly saw was a mayor who seemed uncomfortable in his own skin, who often hid behind a wall of canned news releases from his office, and who had his tough lieutenants, Penny Ballem and Mike Magee.And so, in the era of combative and sometimes fact-free Twitter, he became the mayor who was in the pocket of big developers, who had a bike lane put in near his house to increase its value, who was directly responsible for the streets not being ploughed of snow. (Another mayor in the region recently said to me, “When they start to blame you for the snow, it’s time to leave.”)He still is admired by many, especially for the green initiatives, the opposition to the Kinder Morgan pipeline, the dogged approach to trying to improve the city’s housing options. We don’t hear much from those people these days. They’re drowned out by the ones angry over other issues.They say that history is the story told by the winning side. So it’s hard to say now what place Gregor Robertson will come to hold in history. It will depend on who wins the next battle for Vancouver.