Dave Winfield only spent one season with the Blue Jays, but his role in helping Toronto win the 1992 World Series made him a legend in the eyes of Hogtownians. That wasn't always the case, though. After a 1983 incident in which Winfield killed a seagull during warmup tosses—an incident that earned him animal-cruelty charges—Blue Jays fans taunted him for years with chants of "Bird Killer!"
All of which makes his appearance in this television spot for Toronto tourism even stranger. We can't place the exact year this commercial was made—it looks like 1985, but it could be anywhere between 1984 and 1988—but it's part of what turned out to be an ill-fated attempt by the city to create a tourism campaign in the vein of "I ♥ NY."
The campaign itself was controversial from the start. City leaders from the nearby suburbs objected to its singular focus on Toronto, while the October 20, 1984 Globe And Mail features the following quotation:
Mothers certainly won't want Discover The Feeling plastered all over the fronts of their teen-aged girls' T shirts.
The campaign ended in 1989 when Toronto chose a new slogan: "Couldn't You Use A Little Toronto?" None of this helps us answer why the city included one of its villains in the ad campaign, though our best guess would be that Winfield offered to be a part as an attempt to repair his relationship with the city. We've contacted Winfield's people to see if he can give us some more information on how this came to be.