The latest in the continuing saga is the emergence of more surreptitiously shot cellphone footage of the mayor, including a video that shows him in a restaurant while seemingly intoxicated, spouting obscenities and rambling incoherently in a Jamaican patois.
Ford responded to the video by saying, "what I do in my personal life with my personal friends, that's up to me… It's my own time."
Toronto Councillor Michael Thompson, however, said the latest episode demonstrates that Ford is no longer fit for office and called for him to step down.
The footage and the ensuing criticism has reignited the age-old debate over how much privacy a public figure can expect to have.
Since he was elected to office, Mayor Ford has sometimes sought to keep his private life out of the public eye. But critics argue that his personal style has also succeeded in blurring the lines, and that he has brought many of these so-called intrusions on himself.
'I'm always available,' Ford says
For example, Ford has a reputation for handing out his personal phone number and email address so that Torontonians can contact him at will.
Ford has said that he is determined to serve the city and that he is open to comments, criticism and questions.
"I'm always available. It's pretty hard to hide 300 pounds of fun," said Ford at the beginning of his term.
The mayor has blurred the lines, however, by using official city hall letterhead to pen letters of reference for personal friends (and convicted criminals) Sandro Lisi and Douglas Sedgwick and to solicit donations to his football foundation.
He also appears to have used his clout with the Toronto Transit Commission on one occasion to reroute city buses to pick up the football team he coached when an incident at a game resulted in a call to police.
Many of these incidents seem to roll off the mayor's back. But since finally admitting in November that he had, indeed, smoked crack cocaine, as Gawker and the Toronto Star had first alleged, Ford's private life came under even more scrutiny.
Where does he draw the line?
Pollster Michael Marzolini at Pollara Strategic Insights says there are limits to what the public is willing to accept, even when it comes to reporting on public figures.
"When asked about things like hair transplants, the public says, we don't have a right to know that. That's not in our interest. What is in our interest are character issues," he says.
According to Marzolini, Canadians in general are not fussed about the private lives of politicians unless there is a perceived moral fault that could affect their judgment.
Historical leaders such as former U.S. presidents Dwight Eisenhower and John F. Kennedy had affairs, but their private lives were not dragged into the public sphere as they are today, Marzolini observes. There was a tacit understanding between politicians and the press gallery.
But "the media has changed and set its own boundaries and ethics," he says. "There was no real breaking of the dam, it has been a slow evolution.
"The public demand is changing. They want to know, not because it's salacious, but because they want to know the character of the people governing them."
In Marzolini's view, the transition to transparency can be partially credited to the onslaught of reality TV shows. But it's clear the cellphone revolution has played a role as well.
"I think it's fair to say that there is an expectation when you're the mayor of the city that you're 24/7, because you know emergencies can strike at any time and you have to be in a position to respond and lead," said Rocco Rossi, a longtime campaign manager who ran for mayor himself in 2010 against Ford.
He adds, "We live in an age where there are cameras everywhere, and there is an expectation of leadership."
Toronto Councillor Denzil Minnan-Wong has said he agrees that the mayor is entitled to a private life, but said that in the case of the latest videos, Ford was not in a private place.
Adam Giambrone, another candidate who went up against Ford in the 2010 mayoral election, knows about private lives under public scrutiny.
Giambrone was forced to drop out of the race after a newspaper published an interview with a student who was having an affair with Giambrone, who was engaged to someone else at the time.
"When you’re out at a restaurant, people are going to be aware of your presence,” Giambrone said. "You do deserve some privacy. You deserve some chances to relax, but [lack of privacy] goes part and parcel with the job.
“I think the mayor, like him or not, deserves a degree of privacy. I think his home life deserves privacy. What he does on his own time, I think, is his own business.”