To the Point: Ontario Election Day Special
To the Point: Ontario Election Day Special
With the Ontario election barrelling toward February 27, the province’s 124 ridings are heating up—but not all are equal. Some are straight-up political cage matches, loaded with high stakes, big names, and enough drama to keep even the most jaded operatives on their toes. Here’s our rundown of the 10 ridings that’ll shape the narrative when the ballots drop. Buckle up.
Mississauga East—Cooksville
Bonnie Crombie’s make-or-break moment. The Liberal leader’s banking on her old mayoral stomping grounds to catapult her into the legislature after 15 months of sideline quarterbacking a nine-MPP caucus. No incumbent here—ex-PC Kaleed Rasheed resigned after the Greenbelt scandal—but Doug Ford’s Tories still own Mississauga’s turf. Enter Silvia Gualtieri, insurance exec and Patrick Brown’s mother-in-law, swinging for the PCs. Crombie’s past tussles with Brown in Peel politics add spice. NDP’s Alex Venuto and Green David Zeni round out the card, but this is Crombie versus Ford, round one. A loss here could tank her momentum.
Eglinton—Lawrence
Toronto’s PC fortress got wobbly when Robin Martin decided not to seek re-election after serving two terms. Liberals smelled blood, and then the NDP’s Natasha Doyle-Merrick pulled a curveball—dropped out to back Liberal Vince Gasparro and dodge a vote split. Bold move. It’s now a straight fight: Gasparro, ex-Tory aide turned finance hotshot, versus PC fundraiser Michelle Cooper. The NDP’s Marit Stiles wasn’t thrilled, but Crombie’s camp crowed, “Even they know it’s Bonnie versus Doug.” Green Leah Tysoe’s in the mix, but this riding’s a litmus test for anti-Ford unity. Watch the margins.
Hamilton Centre
Sarah Jama’s Independent reign gets a stress test. Kicked from the NDP in 2023 for going rogue, she’s got a loyal base, but the NDP’s betting on Dr. Robin Lennox, a McMaster doc with street cred in the Hammer. Party brass wants this riding back; it’s Andrea Horwath’s old turf. Liberals field Eileen Walker, PCs tap Sarah Bokhari (who got into a mess of her own this week), and Greens run Lucia Iannantuono. Jama’s the favourite, but a split left vote might hand it to the Tories.
Etobicoke—Lakeshore
Liberals came within 842 votes of PC Christine Hogarth last time, and they’re all-in now with Lee Fairclough, a health-care heavy hitter. She’s hammering Ford on wait times and doctor shortages—smart play in a riding that’s swung tight. NDP’s Rozhen Asrani and Green Sean Garcia are in, but this is Fairclough versus Hogarth, take two. If Liberals can flip this, it’s a signal Ford’s urban grip’s slipping.
York South—Weston
Michael Ford’s exit—nephew of the Premier—cracked this riding wide open. NDP’s Faisal Hassan wants his old seat back, banking on pre-2018 Liberal vibes. PCs counter with Mohamed Firin, a Ford loyalist, while Liberal Daniel Di Giorgio and Green Lilian Barrera vie for scraps. Ford’s health leave and cabinet stint left a mark; this one’s a toss-up with turnout as kingmaker. Chaos breeds opportunity.
Haldimand—Norfolk
Independent Bobbi Ann Brady stunned in 2022 with Toby Barrett’s blessing. Now, she’s defending her turf against PC Amy Martin, Norfolk’s mayor on leave. Barrett’s still stumping for Brady—rare loyalty in this game—but Ford’s crew wants it back. Liberal Vandan Patel, NDP Erica Englert, and Green Anna Massinen are in, but this is Brady versus the machine. Can an Indie hold? We’re skeptical.
Oshawa
NDP’s Jennifer French faces a ghost from the past: ex-PC MPP Jerry Ouellette, who she smoked by 7,000 votes in 2014. Last time, her edge shrank to 757—Ford’s labour push nearly flipped it. Liberals turfed Viresh Bansal over old tweets; Green Nicholas Sirgool steps up. French’s incumbency’s an edge, but Ouellette’s name recognition keeps it tight. A PC upset here would sting Stiles bad.
Ottawa Centre
NDP’s Joel Harden bolted for federal glory, leaving ex-councillor Catherine McKenney to carry the orange flag. They crushed the 2022 mayoral vote downtown—cred to lean on. Liberal Thomas Simpson and PC Scott Healey are swinging, with Green Simon Beckett in the wings. McKenney’s urban base could hold, but a Liberal surge might spoil it. Eyes on turnout.
Parkdale—High Park
Bhutila Karpoche’s federal jump puts this NDP stronghold in play. Alexa Gilmour’s the new orange hope, but Liberal Nadia Guerrera’s got history, and PC Justine Teplycky brings Queen’s Park chops. Green Anna Gorka’s a local fixture. Past races were nail-biters; this one’s a three-way scrum. NDP’s grip’s at risk if the vote fractures.
Oakville
Ford’s condo push into Oakville’s backyard has turned Oakville into a fight for Stephen Crawford. The PC incumbent's political life was put in jeopardy when the government greenlit a 27-storey tower over local objections in late 2024—residents hate it, and Crawford may pay the price. Bonnie made a stop in the riding to stump for her candidate Alison Gohel on Wednesday afternoon, betting she can steal the riding away from the PCs. Mark this down as a toss-up.
The Big Picture
These 10 ridings are the crucible where Ford’s grip, Crombie’s ambitions, and Stiles’ relevance face the fire. Tariffs might hog the spotlight, but healthcare and affordability could quietly tip the scales. With days to go, expect the unexpected—oppo vaults are still loaded. We’ll dissect the wreckage next week.
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ONpoint Strategy Group is all about helping clients make an impact where it counts. Specializing in government relations and strategic execution, our team—Nico Fidani-Diker, Mariana Di Rezze, Krystle Caputo, David Morgado, Christopher Mourtos, Ellen Gouchman, Brandon Falcone, and Mike Britton—works closely with clients to navigate complex political landscapes and bring their goals to life. With a practical, results-driven approach, we build strong relationships, craft winning strategies, and make sure every step brings clients closer to meaningful outcomes. We’re passionate about making sure our clients are heard, supported, and positioned for success.
