Maple Leaf Gardens – World Welterweight Championship – Jose Napoles vs. Clyde Gray

If Muhammad Ali defeating George Chuvalo in 1966 was Toronto’s most famous prize fight, José Nápoles defending his welterweight title against Clyde Gray in 1973 might be the highest-stakes matchup ever fought in the city. Nápoles, a Cuban based in Mexico, and Gray, a Toronto-based Nova Scotian, were both top-tier welterweights near their primes. Ali attended as a spectator and received a standing ovation from the audience. Nápoles and Gray delivered a thrilling match between master boxers, and Nápoles knocked Gray down once before winning.

Maple Leaf Stadium

Born in Toronto, Canadian and Commonwealth boxing champ Larry Gains was nicknamed “The Toronto Terror.” Gains was a skilled, elusive boxer, who, for all his success, never fought for a world heavyweight title – a de-facto ban on Black challengers kept that championship segregated. But Gains competed for and won the “World Colored Championship” several times, including against American boxing legend George Godfrey at Maple Leaf Stadium in 1928. Godfrey was disqualified after hitting Gains with a blatant low blow. According to The Globe and Mail, the below-the-belt punch dented Gains’ aluminium groin protector. 

Air Canada Centre – Adonis Stevenson vs. Badou Jack

Toronto hadn’t hosted a world title boxing match since 1984, so when the world light heavyweight championship was scheduled in 2018, a question arose: could high-level boxing still thrive in the city? In the ring, Adonis Stevenson, the champion from Montreal, and Badou Jack, the challenger from Sweden, engaged in a dramatic brawl filled with momentum shifts, power-punching, and resilience. The judges scored it a draw; fans made it a success. The bout was moved from Montreal to Toronto on three weeks’ notice, but still drew 5,000 spectators. It remains the only boxing world title fight to take place at the venue now known as the Scotiabank Arena.

Sully Gym’s, founded in 1943, is the thread that connects much of Toronto’s post-1940s boxing history. Muhammad Ali worked out there for the 1966 World Heavyweight fight against local hero George Chuvalo. Lennox Lewis trained there before representing Canada at the Los Angeles Olympics in 1984. In March 2019, Sully’s faced eviction. “It’s an old-school gym and I try to keep it that way,” head coach Tony Morrison told the Toronto Star. “But everywhere you go, the rents have gone up.”  A $30,000 fundraising campaign enabled Sully’s to move its current spot on Dundas St. West, in the summer of 2019.

Maple Leaf Gardens – World Heavyweight Championship

When the United States decided to enter the Vietnam War in 1965, public opinion was mixed. Muhammad Ali, the reigning world heavyweight champion, publicly opposed the war on moral and religious grounds. His stand affected his career – sales for a scheduled fight against Jimmy Ellis in 1966 slowed to a trickle, several American cities declined to sanction the bout, and Ellis pulled out. Lucky for Toronto, organisers offered up Maple Leaf Gardens as a venue. George Chuvalo, a local fighter and five-time Canadian heavyweight champion stepped in as Ali’s foil. The 13,918 people in attendance saw 15 rounds of peak ali: a fast, fluid puncher and savvy self- promoter, fighting his way to a place in history. Only one year later, Ali was stripped of his heavyweight title and boxing licence after refusing induction into the U.S. Army. 

Varsity Stadium – Aaron Pryor vs. Nick Furlano

Aaron Pryor, the Cincinnati-born champion, came out of retirement to defend his International Boxing Federation title facing Nick Furlano, a Toronto-based challenger with whom he had a lot in common. Both boxers grew up tough, and lived on their own as teenagers. Both battled addiction during and after their careers. This fight, staged at University of Toronto’s Varsity Arena, saw Pryor, a feared power puncher, knock Furlano down in the first round.  Furlano, surprisingly, survived that knockdown and lasted all 15 rounds, becoming the first fighter to go the distance with Pryor since 1977. Their meeting would be the last world title fight in Toronto for the next 34 years.

Maple Leaf Gardens

Even though the day’s main event was Toronto’s Clyde Gray versus American Sammy Rookard, history remembers American boxer George Foreman on this night. Six months after losing the heavyweight title to Muhammad Ali, Foreman appeared in Toronto to fight five journeymen… consecutively over the course of an hour. Whatever Foreman thought he would prove didn’t matter. The crowd booed him, and Ali mocked him from the ringside, where he was working as a commentator alongside legendary journalist Howard Cosell. The action was sloppy, disjointed, and forgettable. Cosell called it “the weirdest thing you will ever see.” Whether this was the reason or not, Maple Leaf Gardens never hosted another boxing event.  

American Club, Paris

One of history’s strangest boxing matches took place in Paris, France, between two Toronto Star writers. American novelist Ernest Hemingway was a foreign correspondent for the Star, as was Toronto-based author Morley Callaghan. The two writers become friends as well as sparring partners. Hemingway, often described as a “macho blowhard,” claimed to be one of the world’s great boxers, but he was no match for Callaghan. Their friend, American author F. Scott Fitzgerald, was asked to serve as timekeeper. Fitzgerald let a round go too long, and Callaghan knocked Hemingway to the mat. Hemingway never forgave Fitzgerald; it was the end of their famous friendship.

Varsity Arena – Donovan Boucher vs. Shawn O’Sullivan

This match was international. Shawn O’Sullivan won Olympic silver in 1984 in Los Angeles, while Donovan Boucher had world title ambitions. It was also personal, as the men had been sparring partners in the past. And it was intensely local: O’Sullivan was the pride of the Cabbagetown Gym, while Boucher got his start at Toronto’s Sully’s Gym. Each man drew a passionate group of supporters to Varsity Arena on fight night, but the bout itself was one-sided. Boucher, younger and quicker, beat O’Sullivan to the punch repeatedly before knocking him out in the second round. Afterward, O’Sullivan announced the first of his three retirements. 

Even Sports Illustrated, which had launched in 1954, sent a writer. The winner of the bout would face Floyd Patterson for the world heavyweight championship. Parker was 17 years younger and almost 25 pounds heavier, but Moore, nicknamed “The Old Mongoose,” had the edge in technique, tactics, and pure power. He beat Parker to the punch over eight bloody rounds before stopping him. “Don’t believe all that stuff about Archie [Moore] being 43 years old,” Parker told reporters. “That’s malarkey. He can really step.” Ticket sales totaled $148,5000, the equivalent of $1.6 million today.