Why Jagmeet Singh’s NDP thinks Olivia Chow holds the key for capturing Toronto

OTTAWA—The mood among federal New Democrats the morning after Olivia Chow was elected Toronto’s next mayor was a little different than it was one week ago.

Last Tuesday, the party was taking stock of their performance in a quartet of federal byelections that saw their vote share drop across the board compared to the last election. At the time, the NDP spun it this way: all four ridings were locks for other parties, byelections tend to maintain the status quo, and low voter turnout rarely favours the New Democrats.

But this Tuesday, Chow’s victory in a mayoral byelection led the party to a rather different conclusion. Insiders say the former NDP MP’s win suggests Canada’s largest city was looking for progressive change after more than a decade of conservative rule — and it turned to a stalwart among New Democrats to usher in that era.

“People are just ecstatic,” said Jennifer Howard, chief of staff to NDP Leader Jagmeet Singh.

“Many folks in this party have known Olivia for a long time and have been there for both the wins and losses. I think they’re just tremendously pleased to see her win, to see her run such an authentic campaign with … the values of New Democrats. It was a really great win for everybody.”

It’s easy to see why the NDP is eager to latch on to Chow’s success.

Justin Trudeau pushed the NDP from Toronto

The party has had zero federal representation in the GTA for the past eight years. The last time it did was in 2011, when Chow, along with her husband and former NDP Leader Jack Layton, were two of eight NDP MPs who won seats in Toronto. The party lost them all to the Liberals when Justin Trudeau secured a majority government in 2015, locking themselves out of a vote-rich region deemed a key pathway to federal victory.

It’s remained an area the NDP covets, and when the next federal election rolls around, it’ll be led by a political veteran who launched her career in an NDP constituency office in the 1980s and has remained a close ally of the party ever since.

“She’s going to have a lot of friends at the federal level in the New Democratic Party. I think for ridings from Toronto, Danforth, Beaches, and Davenport, they will certainly be a big pickup, and I think, significantly, Scarborough,” said Ontario NDP MP Charlie Angus, one of the province’s remaining MPs who served with Chow in the House of Commons.

Chow weathered two failed attempts to lock down the former riding of Trinity-Spadina before wresting it away from the Liberals in 2006, holding on to her seat when the NDP formed the Official Opposition for the first time in 2011. She ruled out running to replace Layton as NDP leader following his death in 2011 — though there was interest in her doing so — and stepped down from federal office in 2014 to mount a failed bid to succeed Rob Ford as mayor of Toronto.

But there is plenty of present-day overlap between Chow and the federal party, Howard said, offering a renewed shot of optimism for a party hoping to reclaim lost ground.

Key figures in Chow’s campaign team have ties to the federal party: one is her campaign director, Michal Hay, who also guided Singh to his leadership victory in 2017.

Singh, who has long drawn inspiration from Chow, also crossed paths with the mayor-elect several times on her campaign trail and supported her bid. Chow has previously done the same: Howard said she has been instrumental in the past two federal elections, hosting events in her home, appearing with Singh at events and convincing under-represented candidates to run in Toronto and across the country.

“She’s often somebody that we will turn to not only for ideas, but sometimes for help talking to candidates who may be reluctant or uncertain of their ability,” Howard said.

“She’s worked with our caucus on how to better tell our story, how to better connect with other people’s stories.”

NDP want to know how Chow won

The party isn’t only looking at Chow as a potential ally to make inroads ahead of the next election. They’re also looking at how she won.

“She didn’t only win in the places she was expected to win, sort of downtown Toronto areas, but also in places like Scarborough, which in the past has also been a seat that we have held provincially and federally,” Howard said.

The NDP will also be looking at spots like Davenport and Parkdale-High Park, which Chow handily won despite her chief rival Ana Bailão securing the backing of federal Liberals in the area.

But whether Chow will be able to throw her weight behind the NDP come federal election time is another issue: the mayor-elect has had to fend off questions over whether she will be able to govern as a non-partisan.

As for whether she will play well with the prime minister, who once sat alongside Chow in the lower chamber as an MP, a senior Liberal government source told the Star that Ottawa saw in yesterday’s vote a desire for “progressive” housing and transit policies, which are priorities of Trudeau’s as well.

Those are also areas of alignment between Singh and Chow, and that’s where the minority Liberals’ governing agreement with the NDP offers a chance for collaboration, said former Toronto NDP MP Peggy Nash, who also served with Chow.

“I think the new mayor has to work with who’s there and who’s there federally are the Liberals,” Nash said.

“(The deal) presents an opportunity for the new mayor of Toronto to build on that relationship … to say, ‘We are not going to agree on everything, but let’s find out where we can agree and let’s move forward.’ I think that’s what the supply-and-confidence agreement has shown us and it could absolutely be a path for the city of Toronto,” she added.

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