I thought it could be fun to play along. What might change, for better or worse, if this really happened? Dunkin' or Timmy's?

O'Leary Ventures Chairman Kevin O'Leary weighs in on President-elect Donald Trump's proposal to have Canada join the United ...

Donald Trump has escalated his trolling of Justin Trudeau, arguing that Canadians would pay lower taxes and receive better ...

Kevin O’Leary, of Shark Tank fame, says half of Canada is “interested” in merging with the U.S.—a longshot arrangement that ...

'The Five' panelists react to Kevin O'Leary claiming half of Americans want to join the U.S.

Trump combined his Greenland takeover fantasies, Trudeau trolling and Panama Canal gripes into one Christmas wish.

President-elect says hockey great ‘had no interest, but I think the people of Canada should start a DRAFT WAYNE GRETZKY ...

Trump suggested that Canadian hockey star Wayne Gretzky should run for prime minister, although he said "governor of Canada." ...

President-elect Donald J. Trump has threatened to impose tariffs on Canadian exports unless the country stops the flow of ...

Two top Canadian Cabinet ministers have met with President-elect Donald Trump’s nominee for commerce secretary at Mar-a-Lago ...

O’Leary’s interest in unifying the US and Canada comes after Trump, 78, has repeatedly suggested in recent weeks that Canada ...

Donald Trump is offering Canadians a reduction of 'more than 60%' in taxes if their government joins America as its 51st ...