But he came across as a shallow blowhard during an interview on his Lange & O'Leary Exchange show with Pulitzer Prize-winning journalist Chris Hedges in New York about the Occupy Wall Street movement.
The Twitterverse backlash against the bullet-headed Toronto businessman was equally brutal.
Hedges, a former New York Times foreign correspondent and prolific author on social issues, sympathizes with the protesters camped on Wall Street. But he might have been forgiven for thinking an interview on Canada's public TV network would be a little more high-toned.
Instead, O'Leary tore into Hedges, whom he misidentified as a protest organizer, and denigrated the protesters with oft-repeated criticism that they're unfocused and leaderless.
"They want to reverse the corporate coup that's taken place in the United States, that's rendered the citizenry impotent," Hedges replied.
"You sound like a left-wing nutbar," O'Leary said.
Watch the video:
"I don't usually appear on shows who descend to character assassination," said Hedges, clearly surprised by the personal attack but refusing to be baited. "You sound like Fox News."
He went on to praise the ideas of Canadian thinkers such as John Ralston Saul, and the prudent banking system that helped Canada avoid the 2008 financial crisis that's one of the motivating forces behind the Wall Street protest.
The "interview" ended civilly and O'Leary's co-host thanked Hedges "for joining us."
"It'll be the last last time," the former war correspondent replied.
Viewers clearly felt the blustering O'Leary was no match for the even-tempered, articulate Hedges.
"Disgraceful CBC journalism by Kevin O'Leary with Chris Hedges," tweeted Fred Wilson. "Hedges answers brilliantly but why does CBC allow this?"
MrsPremise4 wondered if Hedges was on Twitter: "I feel the need to apologize on behalf of my nation. Kevin O'Leary is an embarrassment."
"The definition of painful? Watching the CBC's Kevin O'Leary try to take on an intellectual giant like Chris Hedges," tweeted Imofl.
"If, like me, you wish Kevin O'Leary would go to the US and stay there, remember Dragons' Den is the No. 1 snow on CBC TV," Joshua Hind pointed out.
Warren Frey noted the late Steve Jobs "once chewed out Dragons' Den (expletive) Kevin O'Leary all the way to the Apple parking lot," linking to a Globe and Mail article where O'Leary compares himself to the "tooth fairy" beside the "ferocious" Apple visionary.
For his part, O'Leary's Twitter feed ignored the furore, preferring instead to focus on how his memoir, Cold Hard Truth, was doing on the book sales charts.