Toronto’s 10 biggest moments in sports in the last 50 years

To celebrate Toronto Life’s 50th year, we’re counting down the biggest Toronto moments of the last half-century. This time: a ranking of the athletes, tournaments and trophies that mattered most

Penny Oleksiak
Penny Oleksiak Photograph by Getty Images
With a record-breaking medal haul, a 16-year-old swimmer became a national hero

10 Canada’s answer to Michael Phelps? A Pokémon Go–playing teenager who studies at Monarch Park Collegiate. In six days, Penny Oleksiak won four Olympic swimming medals in Rio—a gold, a silver and two bronze—breaking virtually every record statisticians thought to check.


José Bautista
José Bautista Photograph by Getty Images
The bat toss heard round the world

9 José Bautista’s post-homer heave-ho in last year’s ALDS made more noise than the actual World Series. It inspired endless harrumphing about respect, a million memes and at least a few ugly Christmas sweaters. More importantly, it proved the Jays—fresh off the longest playoff drought in pro sports—were out for revenge.


Pan Am Games
Pan Am Games Photograph by Daniel Neuhaus
The Pan Am Games’ legacy had little to do with sports

8 At first, Torontonians stuck up their noses at the Pan Am Games. For good reason, as time revealed: expense-account scandals, a lame mascot, no-take-backs bonuses handed out to execs who blew through their $2.2-billion budget. But the event took over (and won over) the region just the same, leaving us with top-notch athletic facilities, new transit infrastructure and affordable housing, all of which lasted long after Kanye left the building.


Cassie Campbell
Cassie Campbell Photograph by Getty Images
Cassie Campbell spearheaded Canada’s vengeance

7 The Canadian women’s hockey team won silver to the U.S.’s gold in the sport’s Olympic debut in 1998. Four years later, Richmond Hill hero Cassie Campbell led the squad to meet their southern rivals in the finals again. Canada had lost eight straight to the Americans, but U of T alumna Jayna Hefford slapped home the winning goal, asserting the Canucks’ on-ice dominance. The team has won gold at every Olympics since.


Ben Johnson
Ben Johnson Photograph by Getty Images
Ben Johnson’s dope legacy

6 When Scarborough sprinter Ben Johnson ran a record-setting 100-metre dash at the Seoul Olympics, he electrified his country. When he was stripped of his gold for doping, Canada came crashing down, too. Then-PM Brian Mulroney established the Dubin Inquiry, a painful, soul-searching affair that exposed widespread drug use among Canuck athletes and led to the creation of the Canadian Anti-Doping Organization.


George Chuvalo
George Chuvalo Photograph by Getty Images
The biggest boxing match in Canadian history

5 George Chuvalo’s showdown with Muhammad Ali at Maple Leaf Gardens had all the makings of a monumental matchup: virtuosic athletes, months of anticipation, Canadian-American rivalry. Chuvalo’s imminent retirement and the fight’s potential to return glory to the corruption-plagued sport only upped the ante. And what happened in the ring was even more spectacular than the hype: the heavyweights exchanged punches for 15 bloody rounds. Ultimately, Ali was faster and stronger, but, after his victory, he called Chuvalo the toughest man he’d ever fought.



Donovan Bailey
Donovan Bailey Photograph by Getty Images
Donovan Bailey obliterated Michael Johnson

4 After the 1996 Olympics, Canadian 100-metre champ Donovan Bailey traded taunts with American ace Michael Johnson over who deserved the title of world’s fastest man. They convened at the SkyDome for a 150-metre race to settle it in front of 30,000 fans. Mid-run, Johnson pulled a muscle and Bailey took the prize: bragging rights and a million smackeroos. Not even Bailey’s gripes about the shape of the track or his blockheaded accusation that Johnson faked the injury could overshadow the conclusion: Bailey was the fastest, and he was ours.


Vince Carter
Vince Carter Photograph by Getty Images
Vinsanity revolutionized the NBA slam dunk contest

3 Sportscasters cried no contest after Vince Carter’s first dunk of the competition, a spin-o-rama windmill stunner—to them, the much-hyped king of dunks had already won. Then, wearing Raps purple, he one-upped himself again and again, nailing a now-iconic through-the-legs alley-oop. The routine reinvigorated the lacklustre event, and it’s still considered the finest dunk contest showing of all time.


Toronto Maple Leafs, 1967 Stanley Cup champions
Toronto Maple Leafs, 1967 Stanley Cup champions Photograph by Getty Images
The goal that started the league’s longest drought

2 In the final minute of Game 6, captain George Armstrong slung the puck past the Montreal Canadiens’ blue line into an empty net, clinching the Stanley Cup for his Leafs. In hindsight, what’s more remarkable than the win itself (the Buds already had three Cups that decade) was the 50-year dry spell it began. Today, the mere mention of ’67—a time when goalies didn’t wear helmets, boards had no ads and the Leafs actually stood a chance—still stings, even if most of the club’s current fans hadn’t been born yet.


Toronto Blue Jays , 1992 World Series champions
Toronto Blue Jays, 1992 World Series champions Photograph by Getty Images
BACK TO BACK 1992-1993
Canada conquered America’s pastime

1 The images of Joe Carter pogo-ing off first after the Blue Jays’ World Series win in 1992 and his fist-pumping walk-off celebration a year later have been replaying in Torontonians’ minds for two decades. A million fans flooded Yonge Street after that second win, paralyzing traffic from the waterfront to St. Clair. The victories are local lore, not only because they were the Jays’ first—and only—championships, but also because we finally beat the Americans at their own game. No wonder Drake is still rapping about it.


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