O’Leary Ventures chairman Kevin O’Leary joins Fox News’ Inauguration Day coverage with his perspective on President Donald ...

The CNN commentator reminded the "Shark Tank" investor about his ties to the president-elect in a tense on-air exchange.

Arlene Dickinson, an investor who appears on the popular reality TV show, says former Dragon Kevin O’Leary’s recent comments ...

Kevin O'Leary has detailed the priorities of US President Donald Trump, which include tax cuts, deregulation, tariffs, and ...

Kevin O'Leary, who said a U.S.-Canada merger might make some sense, visits Trump in Palm Beach at Mara-a-Lago with Alberta ...

U.S. President-elect Donald Trump says he would use economic force to annex Canada. Canadian celebrity investor Kevin O’Leary ...

Shark Tank” star Kevin O’Leary declared Sunday that President-elect Donald Trump shot a 68 in golf while the celebrity ...

O’Leary tells On The Money he’s teaming up with billionaire Frank McCourt and has enough money to both build out their own app and buy the name and business from the Chinese — if they are ...

The man hoping Canada would become part of the USA because Trump spewed the idea, Kevin O'Leary, is a dumbass. Appearing on CNN, O'Leary criticized Sen. Adam Schiff for questioning Pam Bondi during ...

The TV personality claims people trust him to make the deal, but a poll found only a small minority of Canadians interested ...

After Trump claimed on social media that Canadians could pay 60 per cent less in taxes by joining the U.S., O’Leary told Fox ...