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Kevin O'Leary
Deep Dives
Turf War: Old money versus new money at the Toronto Lawn Tennis Club
For 148 years, the country’s oldest tennis club was an ivy-covered bastion of civility with a roster of like-minded, blue-blooded members. Then chaos erupted
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Life
What really happened the night of the O’Leary boat crash in Muskoka
It's been a year since the infamous accident, which triggered a swirl of legal manoeuvring, PR gamesmanship and cottage-country gossip
City News
11 Toronto celebrities in cottage country
Including Kevin O'Leary, Yannick Bisson and Tessa Virtue
City News
Inside Kevin O’Leary’s $2,000-a-head fundraiser at Casa Loma, with Mark Cuban and Barbara Corcoran
What went down at Three Sharks in a Castle
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City News
Kevin O’Leary bailed on another Conservative leadership debate, and Twitter was mad
The
Shark Tank
star skipped another major campaign stop
City News
What Canadian conservatives are saying about Donald Trump’s Muslim ban
Ordered from most to least outraged
City News
Q&A: Arlene Dickinson, the former
Dragons’ Den
star who thinks voting for Kevin O’Leary would be a mistake
"Kevin is ultimately about Kevin"
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City News
Who deserves to be called “Canada’s Trump”?
We break it down
Culture
Toronto’s 50 Most Influential: #26, Kevin O’Leary
The TV star who might (or might not) be PM material
City News
Kevin O’Leary is a blowhard, a relentless self-promoter and, maybe, Canada’s future leader
The dastardly reality TV star’s flirtation with a federal leadership bid is sending Tories into convulsions
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City News
Kevin O’Leary on leaving the CBC, learning from Don Cherry, and befriending Dragons
Love him or loathe him, Kevin O’Leary knows how to get your attention—and he’ll have lots more of it in his new role as CTV...
City News
Slideshow: Kevin O’Leary wants to be an artist—and he’s not half bad
Kevin O’Leary is better known for his ego and Dragon Den real-talk than his artistic soul, so we were skeptical when we heard...
Culture
Second time’s a bust for Zane Caplanksy on Dragons’ Den
Zane Caplansky’ s second appearance on Dragons’ Den ended the same way as his first: without a deal. The Caplansky’s...
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City News
Nine Toronto Halloween costumes, from Kevin O’Leary to a condo tower
Since Halloween falls on a Wednesday this year, most of the revelry will be this coming weekend—which means there’s only a few...
City News
Five things we learned about Kevin O’Leary from Report on Business’s scathing feature
Although Kevin O’Leary undoubtedly enjoys the spotlight, there are things the businessman and professional pot-stirrer would...
Culture
TIFF PARTY: The annual Hello! Canada bash drew, appropriately, a swarm of Canadian celebs
Hello! magazine hosted its fourth annual TIFF party at the Ritz Carlton last night, drawing a crowd of mostly Canadian celebs. Our...
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City News
Into the (Not So) Wild: our look at the summer camps of Toronto’s rich and famous
A sojourn to Northern Ontario used to mean grabbing a sleeping bag and a can of beans and roughing it in the woods, all in the...
Food & Drink
These Booths Were Made for Gawking: who sits where at La Société
The cuisine is supremely so-so, but the glitzy atmosphere and A-plus people-watching at La Société—the crown jewel of...
City News
Kevin O’Leary is taking over the world—or at least Toronto’s media
Between Dragons’ Den, Redemption Inc., The Lang and O’Leary Exchange and appearances to flog his book, we thought Kevin...
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Culture
Redemption Inc., episode 9: where are they now?
On Redemption Inc. ’s reunion episode, we learn that none of the contestants have made much money since the competition ended...
Culture
Redemption Inc., episode 8: woman on top
With Jeff gone (at least until next week’s reunion show), we started rooting for former crack dealer Alia—she’s...
Culture
Redemption Inc., episode 7: sex sells (coconut water)
The worst has happened: Jeff, our tattoo-loving, Samson-like hero of Redemption Inc . has been chucked out of the competition...
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Culture
Redemption Inc., episode 6: art is the new crack
Redemption Inc. is getting serious: only five contestants remain and the challenges are becoming fancy (we guess Kevin O’Leary...
City News
Amanda Lang plays host to Toronto’s money at a party for CNN’s Ali Velshi
Amanda Lang, senior business correspondent for CBC News and Canada’s answer to Maria Bartiromo (though, sadly, it’s too late...
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Private School Guide
The Private and Independent School Directory Spring 2025
Big Stories
Deep Dives
Inside the rise and fall of the Vaulter Bandit, the 21st century’s most notorious bank robber
To fellow tourists he met around the world, Jeffery Shuman was a semi-retired developer with a bright smile, an even tan and a fat wallet. In truth, he was a legendary bank robber on the run from the Toronto police and the US Marshals
Deep Dives
Anchor Man: Fox News host John Roberts on Trump, the trade war and the American psyche
If Fox News seems an unlikely landing spot for a guy who got his start pumping out Platinum Blonde on MuchMusic, you probably haven’t heard his thoughts about joining the notorious network, the Canada–US relationship and what he misses most about Toronto
Deep Dives
Trump’s Loss, Toronto’s Gain: Meet the artists, professors, scientists and other luminaries ditching the US and moving north
They’re coming from Big Law, the Ivy League, arts institutes and beyond, brimming with smarts and energy and united by a common cause: avoiding the carnage of Donald Trump. True tales from the brain gain
Deep Dives
Dancing Queens: Patrons, staff and performers share their wildest memories of Crews and Tangos, Toronto’s most storied drag bar
Crews and Tangos has been enforcing the rules of the Village for more than 30 years: wear what you want, kiss who you want, but don’t forget to tip the drag queens. With a condo development looming, we asked around for tales from the iconic spot
Deep Dives
The Joy of Sex with Strangers: A Toronto hotwife’s adventures in ethical non-monogamy
Three months ago, I was a suburban mom in a monogamous relationship. Now I’m sleeping with people I meet online—with my husband’s blessing—and we’ve never been happier. Don’t judge us until you’ve read our story
Deep Dives
The Scandal, the Firing and the Fallout: Anatomy of a Bay Street fiasco at RBC
Nadine Ahn was a high-ranking executive at the bank. Ken Mason, her subordinate, was rapidly promoted. Then someone claimed to see them canoodling at the Royal York, tipped off HR and triggered an inquisition
Deep Dives
Edward the Conqueror: The unlikely ascent of Canada’s telecom king
Edward Rogers was dismissed as a meddling nepo baby—until he muscled out his siblings, acquired his competitors, cornered the telecom market and became the dominant force in Canadian sports
Deep Dives
Lady Parts: Inside Meredith MacNeill and Jennifer Whalen’s new show,
Small Achievable Goals
The
Baroness von Sketch Show
alumnae have elevated joking about women’s issues to an art. Their new show takes aim at menopause. How funny is that?
Deep Dives
Murder in the Blue Mountains: The story behind the killing of Ashley Schwalm
Ashley and James Schwalm had what seemed like a fairy tale life—two wonderful children, fulfilling careers and a gorgeous home close to the private ski club where they’d fallen in love. Then Ashley’s remains turned up in a burned-out car at the bottom of a ditch, and all signs pointed to her husband
Deep Dives
Dark Horse: Inside the fall of Eric Lamaze, Canada’s most famous equestrian
For years, Lamaze was the world’s top-ranked show jumper, living an enviable life filled with fancy cars, international travel and adoring fans—the kind of life a person might do anything to protect
Deep Dives
Dividing Line: How the Bloor Street bike lane turned the city into a battlefield
A few kilometres along Bloor has become Toronto’s most contested strip of concrete, igniting fights over congestion, safety and the future of downtown
Deep Dives
The Chosen One: At just 23, Scottie Barnes is the new face of the Raptors—and the team’s best chance of salvation
Barnes is shouldering the weight of an impatient, basketball-mad city, a hit-and-miss team, and his own colossal ambitions. Does he look worried?
Deep Dives
Almost
Famous: Inside the Beaches’ rise to rock stardom
A viral earworm about a breakup turned the Beaches into Toronto’s hottest export. Now, the panty-throwing, stage-diving, all-girl rock band is seducing fans around the world
Deep Dives
“I was nearly beaten to death by my partner. The case was dismissed because it took too long to get to trial”
How an overburdened justice system is failing survivors of intimate partner violence
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Food & Drink
“We felt disconnected from the outdoors before”: What St. Lawrence Market North vendors think of their new home
And what locally made and grown goods they’re selling
Food & Drink
Sort-of Secret: Amelia’s Market, a Geary Avenue grocer selling local goods and light lunches
Like lovely cheese plates paired with glasses of Ontario-made wine
Food & Drink
“There’s more attention now on shopping close to home”: How Broadfork Produce is connecting Toronto’s top chefs with Ontario farmers
And the west-end supplier is opening to the public soon
Food & Drink
The US tariffs are coming for your espresso martini
With Kahlúa no longer available at the LCBO, Toronto bartenders are getting creative