In 2010, Rob Ford jumped to the mayor's office after spending a decade as a councillor.
Before him, David Miller also went from having a seat on council to being the guy wearing the chain of office, as did Mel Lastman — the first mayor elected to lead the amalgamated city.
Barbara Hall had led the city prior to amalgamation. She, too, had been a city councillor.
Cristine de Clercy, an associate professor in the department of political science at Western University, said it's a trend that is generally reflected within institutions — though there are notable exceptions in politics, including the late Ralph Klein, who jumped from television journalism to the mayor's office in Calgary back in 1980.
"Most institutions recruit, groom and elevate their leaders," de Clercy told CBC News in a telephone interview. "It's quite rare that the leader comes from outside the group."
'Leaders in search of organizations'
So the question then becomes whether Chow and Tory would be considered to be candidates from outside the group of familiar faces grasping for power at city hall.
Chow was a longtime city councillor before she made the jump to federal politics in 2006. She then spent eight years as the MP for Trinity-Spadina, before resigning her seat to run for mayor.
Tory hasn't had a job at city hall, but he did lead the Ontario Progressive Conservatives at Queen's Park. He also ran for mayor in 2003, coming in a close second to Miller.
With such familiarity to Toronto voters and likely with the politicians who are running for office alongside them, it's hard to see Chow and Tory as typical outside challengers in a mayoral race.
"I wouldn't really call them outsiders," said de Clercy, noting that both have continued to seek leadership positions throughout their respective careers.
In some ways, you could think of them as "leaders in search of organizations," she said.
And with their past political ties, de Clercy said they have access to networks of people who can help and support their mayoral bids, unlike more traditional outside candidates.
It's not like running a business
David Siegel, a professor of political science at Brock University, said it may appear to some that the person elected as the mayor of Toronto has a place at the top of the council tree.
"It looks like it's a hierarchy," he said in a telephone interview with CBC News.
But that's not really the case in practice — the mayor has just one vote, the same as the 44 other council members.
Siegel said that for a person coming from the business world, this would be a major shift in thinking, due to the differences in the way that leadership is practised.
At city hall, a mayor must strive for an influential leadership style, as he or she does not have the power to go with a more directive type.
But, getting a grasp on how council works can also be a challenge for experienced council members, like Mayor Ford.
"That might have been Rob Ford's problem," said Siegel, suggesting that the current mayor's struggles at council may have been rooted in an inability to understand why councillors wouldn't do what he wanted.
'A very small circle'
If collegial leadership is required, it means the next mayor will have to be able to rally the people around them.
And if that mayor is Chow or Tory, they will be looking to build relationships with people they haven't been directly working with in the previous term — given the likelihood that many incumbent councillors will return.
De Clercy suspects that won't necessarily be an impediment for either of those two candidates.
"The reality is that Toronto politics is a very small circle," said de Clercy, noting that they will have crossed paths with many council members on previous occasions.
Yet, Chow and Tory will also have a comparatively clean slate to work with, in terms of their personal relationships with any returning councillors.
That won't be the same for Doug Ford, whose time on council is closely tied with his brother's controversial term as mayor, de Clercy said.
The election is just four days away. More than 161,000 of Toronto's estimated 1.6 million eligible voters cast their ballot early through advance voting.