Canada is Boring

In this episode of Canada Is Boring, Rhys and Jesse dive into the bizarre true story behind Amazon Prime’s The Sexiest Man in Winnipeg, following former Winnipeg TV news anchor Steve Vogelsang from 1990s local celebrity and “sexiest man” titleholder to financially ruined, depressed journalism instructor living in his truck and ultimately turning to a hilariously low‑yield bank robbery spree across Regina, Saskatoon, and Medicine Hat. They unpack his “plan” to rob 25 banks for a few thousand dollars at a time using fake bombs and a glue gun, the legal quirks of what counts as armed robbery in Canada, how he was eventually caught after his truck broke down near the scene, his 6.5‑year prison term, and his attempt to rebrand himself as a men’s mental health advocate

In this part two of the Tim Hortons saga, Jesse Harley and Rhys Waters dig into how predatory private equity and corporate ownership have hollowed out one of Canada’s most beloved brands. Building on examples like Friendly’s and Toys “R” Us, they explain how firms use debt-loading, bankruptcy, and aggressive cost-cutting to squeeze short-term profit from companies, and how that model hit Tim Hortons after the Burger King/Restaurant Brands International takeover. They unpack franchisee lawsuits and alleged intimidation, the brand’s fall from a cozy community hub to a transactional, depressing pit stop, and how centralized supply chains, shrinkflation, staff cuts, and PR spin eroded both quality and reputation. The conversation widens to the Temporary Foreign Worker Program, corporate lobbying, and how bad policy and labor exploitation help fuel public anger about immigration and housing pressure, before circling back to a simple call to action: skip the hollowed-out chains when you can, and support local independent coffee shops instead.

Rhys and Jesse kick off a two‑part deep dive into how Tim Hortons went from a beloved Canadian community hub to something that feels strangely empty. They start with personal nostalgia: Jesse’s memories of the late‑90s Tim Hortons as a true “third place” where you’d just show up and see who was there, playing cards, smoking in the glassed‑off section, and chatting for hours. Rhys compares that to the role pubs used to play in the UK, and together they explore how those informal social spaces have eroded over time, feeding into a wider loneliness problem. From there, Rhys walks through the early history of Tim Hortons: NHL defenceman Tim Horton’s partnership with Jim Charade, the rise of franchising, the pivotal role of ex‑cop and Dairy Queen franchisee Ron Joyce, Horton’s death and struggles with alcoholism, and the complicated saga of his widow Lori’s buyout, lawsuits, and the question of what would have been the “right” thing to do for the family and the brand.The episode then traces Tim Hortons’ expansion through its merger with Wendy’s, its growth into Canada’s largest fast‑food chain, and the political optics of Prime Minister Stephen Harper celebrating its return to Canadian ownership. Finally, Rhys introduces 3G Capital, the Brazilian‑rooted investment firm that has built a global empire by acquiring brands like Burger King and Kraft Heinz, then aggressively cutting costs, closing plants, and boosting profit margins while hollowing out quality, staff security, and community connection. With Tim Hortons’ 2014 sale to 3G’s Restaurant Brands International, the stage is set for the “hollowing” of a nostalgic brand Canadians once saw as their national living room.

In this episode of Canada Is Boring, Rhys shares the unbelievable true story of Eddie Haymour, a Lebanese-Canadian businessman who tried to build a Middle Eastern–themed mini theme park—complete with pyramids, mini golf, restaurants, and a giant camel—on tiny Rattlesnake Island in British Columbia. After years of obstruction, permit battles, and discriminatory treatment from provincial authorities, Eddie’s life collapses: his finances are ruined, his marriage ends, his house burns down, he’s confined to a psychiatric hospital, and the government seizes his island—later ruled illegal by the courts. Pushed to the brink, Eddie's next move was impossible to see coming.

When a 69-year-old Churchill, Manitoba resident hears screams outside his home, he steps out in pajamas, slippers, and armed with nothing but a snow shovel—only to find a woman in the jaws of a polar bear. In this episode of Canada Is Boring, Rhys and Jesse dive into the incredible true story of William Ayotte, his split-second decision to attack one of the world’s most dangerous predators, the brutal mauling that followed, and the community effort that saved his life.

In this unexpectedly heavy episode of Canada Is Boring, Rhys and Jesse dig into a part of Canadian history many people never hear about: Canada’s 200‑year relationship with slavery.While many Canadians grow up hearing about the Underground Railroad and Canada as a safe haven, Rhys reveals a much darker past—from New France-era slavery to British rule, and the brutal legal framework that allowed slavery to exist in Canada.Rhys and Jesse take a hard left turn from jokes into one of the darkest and least‑discussed parts of Canadian history: slavery in Canada. From New France’s Code Noir to household slaves as status symbols, from Marie‑Joseph Angélique and Chloe Cooley to the slow legal death of slavery by the 1820s, this episode challenges the myth of Canada as the purely “good guy” of North American history.In the STD Zone, Jesse debriefs his recent trip to Cuba—tourism, cash chaos, and the everyday realities behind the resorts.

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.