It's hard to read the tea-leaves on this one [...]
Actually, it's incredibly easy to read the tea leaves on this one if you do even a smidgen of research. Ford's proclaiming the day like he's done every year since he was elected, and like every mayor of Toronto has done since June Rowlands first did so. No conspiracy or ulterior motive is necessary to explain it.
(And really, Cory, you lived in Toronto for how long? You should know this.)
Edit: Or maybe it was Art Eggleton who was the first? Some sources I've seen say Rowlands explicitly. Others don't give the mayor but say the first year was 1991 or 1990, which would make it Eggleton. Either way: a long time, with a lot of different mayors.