I listened to an interview today on The Current with councillor John Filion. Very interesting, but he related a story about him and Rob frequently making friendly bets on various things, usually sports games on that night. Typically it was just a twenty dollar bill that passed back and forth between them. One day in chambers, something happened and Filion leaned over to Ford and said "I bet your too chicken to run for Mayor?". Ford looked at him and said, "Not for a twenty, make it a grand and your on!"
Filion thinking that a Ford run for mayor would crash and burn, but rid the City of him as a councilman, found 9 other councillors who put up a $100 each to make the thousand and laid the bet. One year later Ford was mayor of Toronto!!!
Sometimes pranks do not go as planned, I guess.
http://www.ctvnews.ca/canada/the-only-av...-1.2584453
http://www.cbc.ca/radio/thecurrent/the-c...-1.3285310