Lastman was a smart businessman, and a great Mayor of the City of North York, but as Mayor of the City of Toronto, he's remembered for some pretty dumb remarks. The general consensus is that he was way out of his depth.
When he was put on a team to drum up international support for Toronto as an Olympic Games site, he gave a press conference about his upcoming trip to Africa and told the press that he had visions of himself and his wife Marilyn being cooked in a big pot of boiling water while a bunch of "cannibals" danced around them. In another part of the same interview, he said that he wasn't really sure about going to Africa because Marilyn was afraid of snakes.
During the SARS epidemic in Toronto, Lastman went on U.S. national TV to reassure American tourists. When asked by his interviewer about the actual number of SARS victims in Toronto, he said didn't know, but that it was very, very small. When asked about the WHO (World Health Organization) travel advisory on Toronto, he asked, apparently baffled, who these people (WHO) were and claimed he had never heard of them. There were other huge gaffes that only Torontonians would recognize.
Once, in a screaming tirade at the man who ultimately succeeded him as Mayor, he told him, "You'll never be Mayor of Toronto, and you know why? Because you say dumb and stupid things." The next day, someone on the Toronto Star wrote that he thought that was a job requirement. Another time he tried to call out the Army to clear the snow off Toronto streets. And yet another time, he seriously proposed that Toronto secede from the Province of Ontario over a tax-distribution disagreement with the Province.
Lastman is actually a great example of a man who excelled in business and as a small suburban mayor (he was winning his later terms by acclamation) but was a total, embarrassing failure in the larger role. I was just kidding when I called him "dumb," he's not "dumb" and probably, neither is Palin, but the point is you can be smart in a minor role and still be a real dummy in a major role.