TORONTO—Rob Ford shocked Canadians when his conservative campaign in 2010 catapulted him into the mayor's office of North America's fifth-largest city, long a haven for left-leaning politics and causes.

Since then, Mr. Ford's tumultuous tenure has captivated Canada's financial capital. He has enraged foes, and some friends, with a number of unpopular policy moves and public gaffes, and local media have fed off his and his family's antics.

"I...