Inside the election showdown in the Toronto suburbs that could make Erin O’Toole prime minister –

About an hour before Erin O’Toole, the man many believe will be Canada’s next prime minister, appeared in the ballroom, a blue van sat blocking the exit lane outside the Crystal Fountain Event Venue in Markham, Ontario. Inside, visible behind a propped up trunk door, lay a stack of blue campaign signs, all bearing the name Melissa Felian. Nearby, two Felian volunteers, blue masks around their chins, struggled to sink another sign into the hard ground beneath the late summer grass.

Markham is the largest city in York Region, a cluster of bellwether suburbs north of Toronto that represents everything that has shifted so far in this federal election. In August, the Liberal party planned to pick up seats in York en route to a majority government. Now, the Conservatives believe the region, home to more people than Ottawa or Edmonton and more swing seats per capita than almost anywhere else in the country, can send O’Toole to 24 Sussex Drive.

“If you look at public polling, York Region … is a much more competitive race than anyone would have expected at the outset,” said Michael Diamond, a longtime Conservative strategist and lobbyist. Winning in York Region, another Conservative told the Star, likely “means a healthy minority.”

In the ballroom that night, before O’Toole jogged in to a kind of electro-Celtic folk banger, it could be felt hanging in the air, impossible to miss: optimism. It’s been a rare enough haze in Conservative circles since 2015. But in Markham, the volunteers, local candidates and party hangers-on were oozing it from every pore.

One woman waltzed into the event wearing what looked like a cape over an O’Toole T-shirt. Near the front of the room, a couple stripped off their masks to pose, grinning, for a photo with Peter Van Loan, a former federal cabinet minister who is now an influential development lobbyist in the GTA.

In front of the podium, laid out in two concentric circles, were seats reserved for the local candidates. Costas Menegakis, a former MP who lost in Richmond Hill to Liberal Majid Jowhari by fewer than 300 votes in 2019, was there, back for a fourth campaign. (He won in 2011, lost in 2015 and 2019). Bob Saroya, the Markham-Unionville incumbent who survived the Liberal wave in 2015 and held on in 2019, held pride of place in the front row.

Felian, who entered the campaign as a distant long-shot in Markham-Thornhill, introduced the leader. There was a funny atmosphere when she spoke — there’s still something odd about the acoustics of a room kept deliberately half empty, even now, 18 months into the pandemic.

“Help me welcome,” she said, “the next prime minister of Canada, Erin O’Toole!”

The Conservatives are arguably doing better in York than even they expected when the campaign started. Some strategists now give Felian a legitimate chance against Liberal heavyweight Mary Ng, for example. Several prominent Liberals, meanwhile, said they were surprised the Conservatives nominated Ben Smith, a 21-year-old self-described “The West Wing” nut, in Markham-Stouffville, a seat that is now legitimately in play.

“The battleground within Ontario is the 905. And that’s where (the Liberals) are on defence right now,” said one Liberal strategist not involved in this campaign. “I think (Justin Trudeau’s compatriots) still have a lot of brand equity and strong local candidates in Peel Region. But York Region is looking tougher.”

Before the campaign, the Liberals had several York seats listed as possible pickups, including Aurora—Oak Ridges—Richmond Hill, home to former Conservative deputy leader Leona Alleslev. Alleslev was first elected in the riding in 2015 as a Liberal. She crossed the floor in 2018 and won a narrow re-election as a Conservative in 2019. (Alleslev was one of two high profile Liberals to leave the party in York Region during Trudeau’s first term, joining former health minister Jane Philpott, who became an independent in 2019.)

Leona Alleslev was first elected in the Aurora?Oak Ridges?Richmond Hill riding in 2015 as a Liberal. She crossed the floor in 2018 and won a narrow re-election as a Conservative in 2019.

Alleslev declined to do an interview with the Star for this story. She also did not respond to a request for biographical and campaign information from Torstar reporter Kim Zarzour or answer questions Zarzour put to all candidates in the riding about truth and reconciliation, the climate crisis, the pandemic and whether or not they would consider crossing the floor (or in Alleslev’s case, consider crossing the floor again).

A former military officer, Alleslev specialized in cost-cutting measures and change management before leaving the Armed Forces in 1996 to join the private sector. For the next several years she worked as a high-profile contractor with the Department of National Defence on aerospace projects. That all ended in 2003, however, after a consulting firm conspired to have her removed from a project, a move that led to more than a decade of litigation and a landmark ruling, in Alleslev’s favour, on the working rights of contract employees.

Despite the win, the case effectively ended Alleslev’s military consulting career. Before getting into politics, she launched two businesses, one in tourism with her husband, and another designing and installing closets and other millwork in Richmond Hill. “I enjoy it, but obviously, I really, really miss my old job,” she told the Ottawa Citizen in 2010. “Closets are fun, but they don’t offer the intellectual challenge and stimulation and the community I had.”

In this campaign, Alleslev is facing Liberal Leah Taylor Roy, whom she beat by about 1,000 votes in 2019, for a second time. On a recent weekday afternoon, on a cul-de-sac on the edge of the Greenbelt, surrounded by new subdivisions, Taylor Roy chased a volunteer toward an open door where a woman stood in her pyjamas looking somewhat confused.

“Hi there,” Taylor Roy said, “I’m the candidate in this riding.” She pointed to a pamphlet in her hand. “This is what I look like without the mask.”

Liberal candidate Leah Taylor Roy canvasses her Aurora?Oak Ridges?Richmond Hill riding ahead of the 2021 federal election.

Taylor Roy comes from something of a political dynasty in York Region. Her father, Tom Taylor, a prominent local Liberal, was the mayor of Newmarket between 1997 and 2006. Her brother, John Taylor, is the current Newmarket mayor.

“My first political picture was when I was age six, and it was a matchbook cover,” she said. It was a photo of her family taken for one of her father’s failed provincial campaigns and handed out as a political souvenir. (Things have changed somewhat in the political swag business. In her father’s era they gave out matchbooks. Taylor Roy’s campaign has branded COVID masks.)

Taylor Roy, a Harvard graduate, grew up around politics, but she didn’t get into the business herself until 2019, after a long career in consulting (including for McKinsey and Company), alternative energy and non-profit management. Between them, she and her husband have six children, including two daughters they adopted from Russia, the youngest of whom turned 18 the year Taylor Roy first took on Alleslev.

There is a different edge to the campaign this year, Taylor Roy said. Off the record, many Conservatives will tell you that what’s fuelling their rise in York Region and other parts of suburban Ontario is anger at Trudeau. And Taylor Roy has certainly felt some of that. One resident yelled “Your leader’s disgusting, you’re disgusting,” at her one night, she said. Another time, a man threatened to shoot a volunteer if he didn’t get off his porch. (The volunteer said he didn’t wait around long enough to find out if it was a serious threat.)

The anger, Taylor Roy said, hasn’t been everywhere, however. For every furious opponent she meets, there have been two others that politely disagree with her. On the afternoon the Star followed her, she walked by one house with two anti-Liberal signs, produced by the far-right Rebel Media. (No one was home.) But the only Conservative voter she actually met was friendly enough.

“They’re definitely there,” she said of the furious protesters who’ve dogged the national campaign, “and they shout more loudly, often. But I wouldn’t say it’s the dominant stream. It’s not the dominant conversation.”

A poll released at the start of the campaign by Mainstreet Research had Liberal Leah Taylor Roy with a significant lead over Leona Alleslev in Aurora?Oak Ridges?Richmond Hill. But more recent polls suggest she's in for a much closer fight.

A poll released at the start of the campaign by Mainstreet Research had Taylor Roy with a significant lead over Alleslev in the riding. But more recent regional and national polls suggest she’s in for a much harder fight.

“In Aurora—Oak Ridges—Richmond Hill our model presently has incumbent Conservative MP Leona Alleslev ahead of Liberal candidate Leah Taylor Roy by roughly 15 percentage points,” said Clifton van der Linden, the founder and CEO of Vox Pop Labs and the lead researcher behind The Signal, an election forecasting tool that aggregates and analyzes public polling data for the Toronto Star.

In fact, The Signal had the Tories up big in most York swing seats in the first week of September, a finding that reflects “broader national trends,” van der Linden said, “but also suggest(s) that this is a region where Conservative momentum is quite strong at the moment.”

That’s not to say the Conservatives have the area sewn up. If the party is nervous about one thing in the region, it’s this: The cities and towns of York are changing and growing fast, possibly even faster than pollsters and organizers can keep up with.

“Anecdotally, everyone’s heard of friends who packed up and (left) the city (during COVID),” Diamond said. Housing prices in the outer suburbs, including most of York Region, meanwhile, have spiked, suggesting at least some of that outward migration has landed there.

Conservatives believe that trend already cost them at least one seat, Milton, last time. They’re wary about the impact it could have this year, especially in York. “One of the pieces of the COVID experience has been people deciding to leave downtown Toronto and move further out into the region,” said Lisa Raitt, who lost in Milton to the Liberals in 2019, and is now out of politics. “Is that something that’s going to make the region more progressive?” she continued. “That’s something that I would watch for during the election.”

But if York Region Conservatives were feeling nervous, they certainly weren’t showing it that night in Markham. Even with the room kept well below capacity, the energy was overwhelmingly positive, even if it wasn’t overwhelming, exactly. The organizers had set up socially distanced chairs throughout the room, but after O’Toole finished delivering his remarks — a lightly modified version of a stump speech heavy on affordability and the many faults of Justin Trudeau — the crowd surged out of their seats and toward the podium.

They surrounded O’Toole in a semicircle. One by one and in groups, they pushed toward the front. They held up their smartphones. They edged themselves into the frame. They leaned into O’Toole, in his focus-grouped corporate casual clothes — a man of the Toronto suburbs, now counting on the Toronto suburbs to make him king.

With Files from Kim Zarzour