The Maple Leafs are one of the oldest, richest and most storied franchises in the NHL, except they haven't played in a Cup final (much less won one) since Gordie Howe was strapping them on for an exhibition game against the Lewis and Clarke expedition. Not only haven't they won, they've been ugly doing it, frequently struggling into the playoffs to lose in the first round, or in recent years never making it at all. This probably has something to do with their being the hockey equivalent of the San Francisco Giants, signing every player over 60 they can.
The NBA Raptors are more prey than predators, and are seldom in the hunt after the first month or so of the season.
The Blue Jays put together back to back Series wins in the '90's but being stuck in the same division as the Yankee's and Red Sox has pretty much barred them from post season play ever since.
Despite this, Toronto fans are among the most over-bearing, ignorant, naval gazing dimwits on the planet. To hear them talk, their cities teams are the dynastic equivalents of the Yankees and Celtics combined.
