Run the Six

How Toronto Helped One Runner Find His Stride

In a city as vast and vibrant as Toronto, there are countless tales of runners as distinct as the streets they move on. For one such runner, the city itself brings special challenges – ones he is channeling into a goal that seemed improbable, if not impossible, just five years ago. Jonathan Greenwald’s story is one of dreaming big dreams, and once they come true, dreaming up new ones.

Jonathan has over thirty races under his belt, including the New York City, Chicago and Boston Marathons, and is gearing up for the Berlin Marathon in September. A resume like that would be a noble feat for any runner, but it’s made all the more impressive by the fact that running wasn’t even a glimmer in his eye five years ago – when he was 40.

When Jonathan moved to Toronto in 2007 from his hometown of Brooklyn, New York, he was newly married and living in a new city he adored. Still, a holdover from the past gnawed at him. “I was really out of shape,” Jonathan recalls. “And I needed to change my lifestyle to feel better about myself.” After some friends recommended he try running, he recognized a new challenge – a practice that would come to define his running life.

He admits, “I was not active growing up. I attempted little league baseball in my teens, but I was awful and quit. When I moved to Canada, I attempted to play hockey with friends, but again, I was awful and quit.” But with running, something clicked. “Running was difficult at first, but I stuck with it and realized I wasn’t awful at it!” (A declaration which should qualify as the biggest understatement in this article.)


To date, Jonathan’s marathon PR is 3:11:17. But, never one to rest on his laurels, Jonathan dreamt up a new challenge: break the 3-hour marathon mark. He’s dubbed the campaign #project25959 on his Instagram channel, @runthesix, where he shares his daily training, challenges and successes on the way to his goal of a sub-3.

“Boston was always a huge goal for me and after participating in the 2018 marathon and qualifying for the 2019 race, I decided I needed bigger, scarier goals,” he says, knowing full well that a clear goal and a clever hashtag alone won’t cut it.

“Attempting to break 3 hours will not be easy. In order for me to come close, I need to change how I approach both my nutrition and strength training,”  he says. “In the nine previous training cycles, I mostly relied on my legs to carry me; meaning a good mix of easy and long runs and a couple of quality workouts each week. I never really focused on nutrition and strength training. But since the end of May, I’ve been really focused on getting healthier, stronger, and faster!”

Then there’s his home turf to deal with.

Not that Toronto isn’t a great city to be runner. “There’s something for everyone,” says Jonathan. “There’s Martin Goodman Trail by Lake Ontario, or the many interconnected trails through the city. Plus, there are no shortage of incredible running crews – and everyone knows Canadians are some of the nicest people in the world. Tag along with any of these crews and you’ll understand why there are so many runners in Toronto.”

But for all the good that Toronto holds for runners, there is one aspect that can prove less than ideal, and that’s the weather. However, it’s not the snow and cold that you might think would bother Jonathan. “I’m sometimes asked if I prefer to run in the winter or summer,” Jonathan says, “and I choose winter every time. I really struggle in the heat.” Which brings us to challenge #3. The goal of a sub 3-hour marathon in Berlin, in September, means looking down the barrel of a hot, humid Toronto summer of training.

So, like the warrior that he is, Jonathan adapts.

“In the cold, you can add additional layers to keep you warm. In the heat, there are only so many layers you can shed to not overheat! So I do most of my running on the Kay Gardner Beltline Trail near my home. It’s a well-shaded area and I can run for 10 kilometres or more, mostly in the shade.” And even though he doesn’t like to carry water when he runs, he stays smart about hydration. “I map out my runs to ensure there are enough water fountains on my route.”

And he gets it all done in his trusty Rides. “I’ve run in every version of the Ride,” he says of his favourite Sauconys. “And the Ride ISO is an absolute dream to run in. It’s so versatile. I wear it on easy runs, long runs, and workouts. I’ve started racing in Kinvaras for marathons, and Fastwitch for shorter distances, but the Ride will always be in my rotation!”

To come so far in such a short running career, and to only pick it up long after a lot of other athletes would have slowed down, is pretty unbelievable – even to Jonathan himself. What would his 30-year-old self would say if told that one day he’d be running close to 3-hour marathons? “I’d say they were delusional for thinking I’d run a marathon to begin with! Even when I started running, 42.2 kilometres seemed an unrealistic distance.

“Never in my wildest dreams did I think I would have as much success as I do now,” he says.

Funny then, how it’s exactly those wild dreams, not to mention a load of hard work, that’s brought him to such heights so far. And with another dream to chase down, in 2 hours, 59 minutes and 59 seconds, it looks like Jonathan’s not done meeting the challenge just yet.

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