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

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 ...

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 sellers.

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 ...

Kevin O'Leary is upset by former First Lady Michelle Obama's decision to skip President-elect Donald Trump's inauguration on ...

O'Leary, who has been a familiar face at Mar-a-Lago since Trump's November election win, posted an image on his X page of him ...

Entrepreneur and “Shark Tank” investor Kevin O’Leary said Wednesday that the ceasefire-hostage agreement between Israel and ...

Canadian businessman Kevin O'Leary said Monday that he told U.S. President-elect Donald Trump that he was wasting his time meeting with Canadian Prime Minister Justin Trudeau.

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 ...

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