One of Canada’s most talented road runners is finally making the leap up to the marathon. Canadian Olympian and 5K national record holder Ben Flanagan will debut over 42.2 km on Oct. 19, close to home, at the TCS Toronto Waterfront Marathon.
At last summer’s Paris Olympics, the 30-year-old from Kitchener, Ont., achieved his career goal of representing Canada on the world stage. Earlier that season, he ran 13:04.62 indoors to qualify for the 5,000m—a time only two Canadians (Moh Ahmed and Justyn Knight) have ever bettered. Still, the roads have always been Flanagan’s specialty.
“To be honest, I think this has been an overdue transition,” Flanagan said in a press release. “A lot of people expected me to make it three or four years ago, which I was very much open to. At this point, it was like, ‘OK, what event will maximize my chances of making a big move at the Olympics?’ I’ve always thought the marathon would be my best event. It might be a late move, but it’s better to do it now—three years before L.A. 2028.”
In June 2024, Flanagan and his wife, Hannah, moved from Ann Arbor, Mich., to Cape Cod, where her parents live. The move came during a period of major life changes: the couple welcomed a baby daughter, and Flanagan switched coaches, joining Jon Green’s Verde Track Club—a move also made by Canadian marathoner Rory Linkletter and The Shakeout Podcast host John Gay.
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“Rory and I were roommates at a lot of training camps in Spain, and at the Paris Olympics,” Flanagan said. “Now we have the same coach. Every time we step on the line, we want to beat each other, but we’re transparent about what’s working and what’s not.”
While Green is based in Flagstaff, Ariz., he and Flanagan stay connected via calls and texts. They meet in person at races or when Green, a Massachusetts native, visits family. Flanagan trains solo most days but has the option to join Boston-based athletes. On long runs, his father-in-law rides alongside on a bike, carrying bottles.

For his debut, Flanagan isn’t setting a hard time goal, seeing Toronto as a springboard into his marathon career.
“The biggest goal is to walk away feeling like I had a positive experience—making as few mistakes as possible, learning from the ones I do make, and knowing I can go faster next time,” he said.
With the L.A. Olympic marathon as the ultimate target, Flanagan knows he’ll likely need to run in the 2:05–2:06 range to earn a spot on Team Canada. “I’m trying not to chase it all at once—just get the first one in, feel good about it, build off that, and hopefully pick up a Canadian championship along the way. It’s a realistic goal.”