Canada is Boring

The story of John Graham, a Canadian diplomat in 1960s Cuba who became an unlikely spy during the aftermath of the Cuban Missile Crisis. Because the United States had no embassy or formal presence in Cuba after the revolution, President John F. Kennedy quietly asked Canadian Prime Minister Lester B. Pearson for help. Pearson turned to Graham, a reserved career diplomat rather than a James Bond‑style operative, and tasked him with confirming whether the Soviets were actually removing their nuclear weapons from the island.Graham declined CIA spy gadgets, including a covert camera, because being caught with obvious espionage equipment would have been too dangerous. Instead, he relied entirely on his remarkable memory, driving around Cuba in check shirts and khakis, observing troop movements, equipment, missile silhouettes, and radar installations from the outside, then returning to the Canadian embassy each day to reconstruct everything from memory, down to distances, serial numbers, and layouts. His detailed reports, cross‑checked with imperfect high‑altitude spy photography, helped reassure Washington that the Soviets were indeed complying, contributing quietly but significantly to the de‑escalation of the crisis. For this work, Graham received no parade or public recognition, simply continuing his career as a successful Canadian diplomat.

In this episode of Canada Is Boring, we dive into the bizarre and morbidly iconic death of Toronto lawyer Gary Hoy, a man so confident in shatterproof glass that he used his own body to prove it. From Bay Street law culture and 1980s Toronto skyscrapers to engineering failures and internet legend, we unpack how a routine office “party trick” turned into one of Canada’s strangest urban myths and staple of “dumb ways to die” lists.Get early access and premium content.

Rhys and Jesse dive into the unbelievable true story of Emma Edmonds, a New Brunswick woman who fled an arranged marriage, reinvented herself as Frank Thompson, and fought for the Union Army in the American Civil War. As a soldier, nurse, and spy, she infiltrated Confederate lines under multiple disguises, including as an enslaved labourer and as an Irish woman, gathering crucial intelligence and surviving brutal battles before malaria forced her to abandon her male identity and return to Canada. Get early access and premium content.

Brian Spencer grew up in remote Fort St. James, pushed toward the NHL by a hard working, hyper-intense sports dad who saw hockey as a path to opportunity. On the night of Brian’s first nationally televised NHL game, his father drove to a CBC station armed and took staff hostage after the Leafs game wasn’t aired, a standoff that ended with his father shot dead as Brian was being interviewed on Hockey Night in Canada.Brian went on to play 10 NHL seasons, only see a tragic end of his own, proving once again that Canada’s relationship with hockey has always been… complicated.Get early access and premium content.

After 499 episodes proving that Canada is anything but boring, we’ve reached Episode 500, and we’re handing the microphone to the people who made it possible.This special milestone episode of Canada Is Boring is a chaotic, heartfelt, occasionally abusive celebration featuring listener voice notes and a best-of clip reel pulled from hundreds of episodes.This episode isn’t a victory lap. It’s a noisy thank-you card to everyone who listened, shared an episode, yelled at us online, or sent a voicemail that forced us to double-check the facts.Onwards to the next strange Canadian story.

In 1886, Canada’s first Prime Minister, Sir John A. Macdonald, finally set out to see the country he had helped stitch together by rail. The Canadian Pacific Railway had just been completed, and a grand cross-country tour was planned, complete with speeches, pomp, and a private rail car.What no one planned for was his wife.Lady Agnes Macdonald was bored.So bored, in fact, that she abandoned the Prime Minister’s private car, climbed into the locomotive cab, blasted the whistle at crossings, ignored orders from her husband, and eventually talked her way into riding on the cowcatcher at the very front of the train, from the Rocky Mountains all the way to the Pacific Ocean.Yes. The outside of the train.Sitting on a candle box.At speed.Through mountain descents, landslides, near derailments, forest fires, and even a full-on pig collision in the Fraser Valley.Joined reluctantly by a deeply stressed government superintendent whose job description rapidly shifted to “human seatbelt.”Along the way, Lady Agnes waved to crowds, dared her husband to join her (he did, briefly), and redefined Victorian ideas of decorum, safety, and common sense—while Sir John A. retreated back to the bar car.Based on “Fur and Gold” by John Pearson (Black Press Media)