When he hit 330, he announced a weight loss contest with his brother Doug, who is junior to him both in political office (a councillor) and size (265 pounds).
Hizzoner ran smack into the time inconsistency problem and after an initial early loss, actually weighed MORE at his penultimate weigh-in in May.
He did however, end up losing 17 pounds but was trounced by his baby bro both in relative and absolute terms (brother lost 33 pounds from a smaller base).
The mayor actually had to be herded onto the scale for the final weigh-in and fell off it awkwardly in his eagerness to get away from the cold hard facts.

Let's go for a politically incorrect breakdown:
Are all the members of Toronto's government from the same family?
Does Toronto choose it's mayor via a pie-eating contest?
The "cut the waist" contest raised $14,000 for charity, which probably wouldn't cover the cost of thanksgiving dinner at the Ford house!
Do read the timeline at the end of the linked article. It's excellent.
Hat tip to Drew M.