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Kevin O'Leary
City News
What
Toronto Life
readers loved and loathed from our January issue
Including our encyclopedic compilation of the city’s best dishes and our interview with Kevin O’Leary, the controversial investor turned actor who debuted in
Marty Supreme
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Culture
Mark Ruffalo wants Kevin O’Leary to shut the f*** up about Billie Eilish
What did Mr. Wonderful say this time?
Culture
Kevin O’Leary was robbed (of an Oscar nom, that is)
And a theory to explain the snub
City News
Marty Supreme
almost ended with Kevin O’Leary doing
what?
They had the teeth ready to go and everything
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City News
Is Ontario having a
Marty Supreme
moment?
Who knew table tennis had such high stakes?
Culture
KPop Demon Hunters
is going up, up, up to the Golden Globes
Clocking Toronto’s big scores and snubs ahead of the season’s first awards show
Culture
Kevin O’Leary got hired to play a “real a-hole” opposite Timothée Chalamet and Gwyneth Paltrow
And what do you know—he nailed the part
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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
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
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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
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
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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"
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
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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
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...
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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...
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...
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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...
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...
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Summer Camp Guide
City News
Summer Camp Directory 2026
Discover our top-rated summer camps for kids of all ages
Wines of the World
Food & Drink
Wines of the World: Rediscover your favourites from
Toronto Life’s
Best Restaurants
From cabernet and merlot to icewine and chardonnay, these wines are primed to pair and delight
Big Stories
Deep Dives
Dead Reckoning: The executor of their estate was supposed to divide it among their friends and family. Instead, he bankrupted it
When Sami and June Suomalainen died, it fell to the executor of their wills, a lawyer they hardly knew, to sell their million-dollar midtown home and split the proceeds among their inheritors. Seven years and six lawsuits later, the beneficiaries haven’t seen a cent
Deep Dives
These are Toronto’s best new restaurants of 2026
This year’s list includes a 150-square-foot omakase counter, a Parisian brasserie in the Annex, Korean comfort food, Filipino karaoke and a Summerhill seafood spot that’s reinventing the raw bar
Deep Dives
Hoop Dreams: Inside the making of the Toronto Tempo, the city’s newly assembled WNBA team
After years of false starts, months of nail-biting negotiations between the league and the players’ union, and an 11th-hour scramble to build a roster, Toronto finally has its own major-league women’s basketball team. Now it just has to live up to the hype
Deep Dives
Live From New York: Inside the slay-or-be-slayed world of Studio 8H with
SNL
rookie Veronika Slowikowska
Slowikowska is the first Canadian to join the cast of
Saturday Night Live
in more than 25 years. She’s also this season’s breakout star. Now all she has to do is keep crushing it
Deep Dives
Better Call Deepak: Meet drug lord Ryan Wedding’s self-styled cocaine lawyer
The man who represented the infamous drug lord is unapologetically flashy—he has a Lamborghini and two Maseratis and wears $1,200 Louboutins. But did he become an accomplice to his client’s crimes? Deepak Paradkar says he was just doing his job. The FBI says he crossed a line
Deep Dives
The Redemption Tour: The Blue Jays are back. Can they finish what they started?
We’re not over it, but they are. Six months after that devastating defeat, the Jays take the field once more, bent more than ever on winning the World Series. Dispatches from the dugout
Deep Dives
My Life as a True Crime Spectacle: My father’s crimes fractured our family. Then came the press
My dad was the infamous Rolex Killer. The news of his crimes nearly broke me. And ever since, my family has been hounded by reporters, podcasters and true crime fanatics—a whole new circle of hell
Deep Dives
Robby on the Line: Out and about with Robby Hoffman, comedy’s equal opportunity assassin
Larry David is the indisputable king of brutal honesty. But if anyone comes close, it’s Robby Hoffman, the suddenly everywhere comic from whom no group is safe
Deep Dives
Notes on an Academic Scandal: Why did TMU demote a leading advocate of DEI?
Pamela Sugiman, a former arts dean at Toronto Metropolitan University, was a key player in the school’s push for diversity, equity and inclusion. When the backlash against DEI arrived, she was demoted. The school says it was a coincidence. She disagrees
Deep Dives
City of Renters: The dream of home ownership isn’t dead. Maybe it should be?
Scenes from the rent-for-life revolution
Deep Dives
This generation was pummelled by Covid high school. Now the job market wants to replace them with AI
It’s hard out here for a 20-something
Deep Dives
The High Price of Hope: Inside Toronto’s white-hot fertility market
Desperate wannabe parents are betting their life savings on unproven treatments and false promises
Deep Dives
Man vs. Machine: ChatGPT caused him to spiral into delusion. Now he’s suing OpenAI
Last spring, a chatbot convinced Allan Brooks that he had discovered a revolutionary mathematical theory. He says it nearly destroyed him
Deep Dives
Smart City: 20 mind-blowing Toronto inventions that are changing the world
Homegrown innovations that will transform lives for the better
Deep Dives
293 Days Without My Son: I gave up everything to rescue my kidnapped child from my abusive husband
When Valentino was abducted, I knew three things: he’d been taken by his father, he was somewhere in India and I would not rest until I found him
Deep Dives
The Violent Life of a Tow Truck Driver: How an unremarkable profession turned Toronto into a war zone
The towing industry has been hijacked by criminals and kingpins who fleece customers, beat up dissenters and shoot their enemies. Inside the brutal turf war for the city’s wrecks
Deep Dives
Street Fight: Inside the battle raging over Toronto multiplexes
If this city stands any chance of solving the housing crisis, it will need buildings with multiple units in residential neighbourhoods—a move that has many residents saying, “Anywhere but here!”
Just Listed
Just Listed
For Sale: 92 Arjay Crescent
As luxury buyers become increasingly focused on wellness, privacy, and long-term livability, a new generation of custom homes is emerging – one defined less by excess and more by thoughtful design
Just Listed
For Sale: 171 Durant Ave
This rare property features 2 houses on 1 lot
Just Listed
For Sale: 50 First Avenue
A testament to time presiding over one of Uxbridge's most storied streetscapes, this magnificently preserved circa 1880 residence commands its prominent corner lot with the quiet confidence of a true architectural landmark
Just Listed
For Sale: 7 Bentley Drive
A commanding architectural statement in prestigious Stonegate–Queensway, this newly completed custom residence by Bali Homes Group presents a refined interpretation of contemporary luxury living
Just Listed
For Sale: 75 Queen Street
Guelph is having a moment