Still, with a year to go until the next election, will the polarizing leader of Canada's largest city manage to win over voters a second time despite the cloud of controversy that surrounds him?
Experts say it's impossible to predict whether Ford — a contentious figure better known for his actions outside city hall — will hold on to his seat.
They're not counting him out, however, and say his larger-than-life personality, combined with the drug-use allegations swirling around him, mean Toronto residents probably won't be the only ones tuning in on Oct. 27, 2014.
"I think the rest of the country will be curious to see who is Toronto going to elect and vote for," said Myer Siemiatycki, a professor of politics at Toronto's Ryerson University.
"It may also be something of a test of how unorthodox can you be as a political leader and still get re-elected," he said.
"The fact that there are a number of unanswered questions and potential improprieties hanging over his head — it is rather unusual for a mayor to head into re-election with that kind of a circumstance around him, but much of his tenure as mayor has redefined what we expect from a mayor."
Ford has already declared his candidacy, though he'll have to wait until January to officially throw his hat in the ring.
His three years at the helm of Canada's largest city have so far been "an unpredictable roller-coaster ride," Siemiatycki said.
The mayor's tumultuous personal life has largely overshadowed his policy decisions, a fact that has frustrated allies and opponents alike.
"I know there's been a lot of distractions with his private life but his public duties have been an absolute disaster. ... Hopefully we'll have a new mayor in a year's time," said Coun. Adam Vaughan, an outspoken detractor.
The "circus and the sideshow" may be what get people talking, but that likely won't be what sways them come voting time, said Ford's former chief of staff, Mark Towhey.
"There's a large segment of people that are unhappy with that circus-like atmosphere, but... there's a huge slice of people who if given a choice between Rob Ford with the sideshow or another mayoral candidate who's going to raise their cost of living in Toronto, they're going to choose Rob Ford," he said.
"It's a kind of personal brand loyalty that people have and they'll put up with a lot of hijinks, especially in an atmosphere where they don't believe most of what they read in the newspaper," he added.
"People talk about his rock star status and that's true... You cannot possibly walk down the street with him without people walking up, they want a picture with him, they want to talk to him."
Ford himself admits he's tired of constantly being chased by the media, telling a group of reporters at city hall Friday that he "can't even breathe sometimes."
"You guys drive me crazy to be quite frank with you," he said. "Cause you never chased any other mayor like you chase me, you don't camp out at any other mayor's house."
Ford's actions have made him somewhat famous abroad as well, grabbing headlines and making him the butt of jokes on late-night television.
He once called in the police after a CBC comedy troupe showed up at his doorstep and has admitted to reading at the wheel to catch up on paperwork.
Last year, he was forced out of office after a judge ruled he violated conflict-of-interest rules but the decision was overturned on appeal before the penalty could kick in.
Then there are this spring's allegations by the Toronto Star and the U.S. gossip site Gawker that reporters have seen a video that appears to show Ford smoking crack cocaine.
The alleged video is also believed to be a factor in a massive gang investigation that led to dozens of arrests in the city's northwest.
Ford has only said he does not smoke crack cocaine and the video does not exist.
"The controversy grows and piles on — whether that has negative electoral consequences is another matter," said Peter Graefe, a political science professor at McMaster University in Hamilton.
Those in uproar over Ford's behaviour probably didn't vote for him to begin with, Graefe said.
"At this point, Rob Ford is unlikely to change the minds of his firmest detractors but at the same time, I think the people who have criticized Rob Ford haven't necessarily done a great job of doing it with a strategy of peeling votes away from him," he said.
"Scandal can be useful if it indicates ways in which Rob Ford has not been a good defender of everyday people's values," he said.
But too often, he said, the mayor's opponents have attacked him in a way that reinforces his image as a man of the people facing off against an out-of-touch elite.
Ford and his councillor brother Doug Ford have consistently painted themselves as the victims of a left-wing smear campaign led in part by the media.
Even Ford's failures often play in his favour, Towhey said.
"The things he's done that haven't gone the way that he wanted them to go just provide more evidence that he's the outsider fighting for the little guy, because in most cases, he's on side with what the average person wants."
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