The city of Barrie had a somewhat similar situation last election. We voted in a new mayor that had been a long time, hard-nose councillor. As councillor he did rub some people the wrong way, but did a solid job and was re-elected more than once in his ward. As mayor, with still only one vote, he was very unsuccessful because he was not able to build a consistent consensus on numerous key issues. He did also seam to step right into several embarrassing messes as well. Last night our incumbent mayor received less than 4% support, but almost all councillors were re-elected.
Ford (leaving his personal troubles and un pc comments aside) was very useful on council because he did count every penny spent, and called people out for their spending. As mayor he still has only one vote and will need to work well with others to accomplish anything. Only in time will we know whether or not he can.