Kevin O’Leary

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

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

What went down at Three Sharks in a Castle

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

Ordered from most to least outraged

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”?

We break it down

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

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

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

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

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