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Kevin O’Leary

What really happened the night of the O’Leary boat crash in Muskoka
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

11 Toronto celebrities in cottage country

11 Toronto celebrities in cottage country

Including Kevin O'Leary, Yannick Bisson and Tessa Virtue

Inside Kevin O’Leary’s $2,000-a-head fundraiser at Casa Loma, with Mark Cuban and Barbara Corcoran

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

Kevin O’Leary bailed on another Conservative leadership debate, and Twitter was mad

Kevin O’Leary bailed on another Conservative leadership debate, and Twitter was mad

The Shark Tank star skipped another major campaign stop

What Canadian conservatives are saying about Donald Trump’s Muslim ban

What Canadian conservatives are saying about Donald Trump’s Muslim ban

Ordered from most to least outraged

Q&A: Arlene Dickinson, the former <em>Dragons’ Den</em> star who thinks voting for Kevin O’Leary would be a mistake

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"

Who deserves to be called “Canada’s Trump”?

Who deserves to be called “Canada’s Trump”?

We break it down

Toronto’s 50 Most Influential: #26, Kevin O’Leary

Toronto’s 50 Most Influential: #26, Kevin O’Leary

The TV star who might (or might not) be PM material

Kevin O’Leary is a blowhard, a relentless self-promoter and, maybe, Canada’s future leader

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

Kevin O’Leary on leaving the CBC, learning from Don Cherry, and befriending Dragons
City

Kevin O’Leary on leaving the CBC, learning from Don Cherry, and befriending Dragons

Slideshow: Kevin O’Leary wants to be an artist—and he’s not half bad
City

Slideshow: Kevin O’Leary wants to be an artist—and he’s not half bad

Culture
Second time’s a bust for Zane Caplanksy on Dragons’ Den
Nine Toronto Halloween costumes, from Kevin O’Leary to a condo tower
City

Nine Toronto Halloween costumes, from Kevin O’Leary to a condo tower

Five things we learned about Kevin O’Leary from Report on Business’s scathing feature
City

Five things we learned about Kevin O’Leary from Report on Business’s scathing feature

TIFF PARTY: The annual Hello! Canada bash drew, appropriately, a swarm of Canadian celebs
Culture

TIFF PARTY: The annual Hello! Canada bash drew, appropriately, a swarm of Canadian celebs

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Private School Directory

The Independent and Private School Directory Spring 2022
Private Schools

The Independent and Private School Directory Spring 2022

Big Stories

“I was so petrified by the scale of the job that I couldn’t sleep”: True tales from the city&#8217;s high-rise construction workers
City

“I was so petrified by the scale of the job that I couldn’t sleep”: True tales from the city’s high-rise construction workers

How I escaped from Manus prison: a memoir
Memoir

How I escaped from Manus prison: a memoir

Where to get a dream cottage for less than you think
Real Estate

Where to get a dream cottage for less than you think

Frank Gehry has a few things to get off his chest
Real Estate

Frank Gehry has a few things to get off his chest

This family built their off-grid dream house for less than $1,000
Real Estate

This family built their off-grid dream house for less than $1,000

The true story of the $46-million heist that shocked the crypto world
City

The true story of the $46-million heist that shocked the crypto world

Tales of love and resilience from Little Ukraine
City

Tales of love and resilience from Little Ukraine

Toronto&#8217;s best new restaurants 2022
Food & Drink

Toronto’s best new restaurants 2022

This man would like your attention
City

This man would like your attention

I was forced into an arranged marriage at 17
Memoir

I was forced into an arranged marriage at 17

Toronto&#8217;s first family of cheese
City

Toronto’s first family of cheese

Twenty-five reasons to love Toronto now
City

Twenty-five reasons to love Toronto now

Inside a high-stakes flight from a crumbling country
Life

Inside a high-stakes flight from a crumbling country

The twisted mind of a serial romance scammer
City

The twisted mind of a serial romance scammer

What should the post-pandemic workplace look like?
City

What should the post-pandemic workplace look like?

How director Domee Shi turned Toronto into a pastel Pixar wonderland
Culture

How director Domee Shi turned Toronto into a pastel Pixar wonderland

How I learned the horrifying truth about my biological father
Memoir

How I learned the horrifying truth about my biological father

Inside a $4-billion family feud
City

Inside a $4-billion family feud

Fifteen mesmerizing photos that reveal the lives of Torontonians in the 1960s and ’70s
City

Fifteen mesmerizing photos that reveal the lives of Torontonians in the 1960s and ’70s

Behind the scenes of an $11-billion subway war
City

Behind the scenes of an $11-billion subway war

Great Spaces

Inside Muskoka Beer Spa, a hop lovers’ utopia in cottage country
Style

Inside Muskoka Beer Spa, a hop lovers’ utopia in cottage country

Best Dressed

Toronto’s Best Dressed: Trish, Mac &#038; Matty Matheson, the ultimate nonconformists

Toronto’s Best Dressed: Trish, Mac & Matty Matheson, the ultimate nonconformists

Toronto’s Best Dressed: Fashion director George Antonopoulos

Toronto’s Best Dressed: Fashion director George Antonopoulos

Toronto’s Best Dressed: Fitness model and anti-blogger Sasha Exeter

Toronto’s Best Dressed: Fitness model and anti-blogger Sasha Exeter

Toronto’s Best Dressed: Brian A. Richards, potential future face of fashion in Toronto

Toronto’s Best Dressed: Brian A. Richards, potential future face of fashion in Toronto

Toronto’s Best Dressed: Artsy supercouple Jeffrey &#038; Lucia Remedios

Toronto’s Best Dressed: Artsy supercouple Jeffrey & Lucia Remedios

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