Name an urban planner?
Robert Moses.
Ebenezer Howard.
Frederick Law Olmstead.
Georges-Eugene Haussman. 
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Jennifer Keesmaat was, and is, an ok planner, and an ok public speaker.  Her answers to questions at meetings I attended did not impress as demonstrating soaring intellectual mastery of her brief.
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But there are worse.  Lots and lots.
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Planning is immensely political.  That is the nature of the beast.
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She should have known that trying to tear down the Gardiner, at all, would be an uphill fight.  Trying to do it before the DRL is built was political folly of the first order.
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That seemed an issue of bad judgment.
As did public fighting with John Tory.
As did insensitivity to everything North of the CP line.
As did unwise use of social media.
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The political capital wasted could have been used to improve transit, now, today.
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She was too young, and much too outspoken (in my view), in a job that requires tact and finesse to build coalitions and consensus.