Indeed it's been hinted for months that Chow — who today officially resigned her Parliament seat — would return to Toronto municipal politics and challenge Ford's bid for re-election.
Chow will officially announce her candidacy Thursday at a news conference in the downtown neighbourhood where her family first arrived in Canada from Hong Kong in the 1970s. Voters will cast their ballots in the municipal election on Oct. 27.
The other top contenders in the race include former Ontario PC leader John Tory, right-leaning councillor Karen Stintz and former councillor David Soknacki.
Here are some key questions Chow faces in the race:
Can she be a credible candidate for fiscal conservatives?
As an NDP MP and the widow of former NDP leader Jack Layton, Chow has to convince centrist voters that she won't spend wildly should she win. University of Toronto political science professor Nelson Wiseman told CBC News that Chow's opponents are sure to question her balance sheet credentials. "She'll stress that she's fiscally responsible ... the others are going to paint her as tax and spend," said Wiseman. Ford already used that angle of attack on Wednesday, saying Chow makes the left-leaning former Toronto mayor David Miller "look like a conservative." Doug Ford, the mayor's brother, said Wednesday he'd like to ask Chow "how much she'll raise taxes."
Can she win in the suburbs?
Chow steps down as the MP representing the same downtown area that she represented as a city councillor. But Wiseman points out that candidates need to attract votes from beyond the downtown core. "You can't win by just winning downtown," said Wiseman. "The old city of Toronto is only one quarter of the city. It's impossible to win an election unless you win the suburbs."
How important will Scarborough be?
This builds on the question above, but many are touting the heavily populated east-end suburb of Scarborough as the race's equivalent of a swing state. It's been a base of Ford support, but it also has a large Chinese population that Chow is likely to target. Former councillor Sandra Bussin said in recent elections Scarborough has been a key battleground. Ford and Stintz are sure to tout their successes in getting council to agree to extend the subway into Scarborough — instead of using light rail along the route — after a long, divisive fight.
Will Chow's 'story' resonate?
Wiseman expects Chow will play up her story of being an immigrant who came to Canada and struggled on her way to success. "You go to a place like Scarborough. You say 'look, my background is similar to yours. My parents came here they had next to nothing. I live downtown in St. James Town, a lot of you did too when you first came. And I worked my way up.'"
Can she separate herself from the pack?
Wiseman said Chow will spent a lot of time pointing out differences between herself and her opponents with messages like: "I don't drive around in a Cadillac SUV like Rob Ford does, I'm not a multimillionaire like John Tory, and I'm not a right-winger like Karen Stintz."
Former councillor Howard Moscoe said he was glad to see Chow jump into the fray.
From his perspective, the election is shaping up to be a three-way fight between Chow, Tory and Ford.
But Moscoe admits that the field of candidates is becoming crowded.
“It’s a scramble. There’s no doubt about it,” he said. “At least there’s a clear choice now.”
Moscoe believes there are “a huge number of people” who are “fed up” with Ford, though he said there are also many voters who relate to him.
Wiseman also said Chow's entry doesn't necessarily hurt Ford's chances.
"Campaigns are very dynamic," said Wiseman. "Who would have thought Ford would win 10 months before the vote?"