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O’Leary reveals the one question he asked Trump at Mar-a-Lago this weekend

2025-01-07

Kevin O'Leary shares details of his Trump meeting & potential purchase of TikTok

2025-01-15

'BAD RELATIONSHIP': O'Leary dishes on Trump, Trudeau relationship amid trade drama

2025-02-03

‘GET RID OF IT’: Kevin O’Leary sides with Trump on fate of ‘stupid’ US penny

2025-02-10

O’Leary says Canada must 'get ready' to negotiate after visit to Mar-a-Lago | Power & Politics

2025-01-14

Kevin O’Leary: This is ‘music to Trump’s ears’

2025-01-21

Kevin O'Leary: Trump judgment left investors asking 'who's next?'

2024-02-20

'GET IN LINE': Kevin O'Leary breaks down Trump's tariff threats at Davos

2025-01-24

Kevin O’Leary: Trump saved the Democrats, too

2024-11-06

Kevin O’Leary weighs in: Could Canada become the 51st US state?

2025-01-09

Kevin O'Leary: Trump reviving Keystone Pipeline would be 'great' for energy independence

2024-11-22

O’Leary predicts ‘riots in the streets’ when Trump’s China tariffs go into effect

2024-12-23

Kevin O’Leary says Trump’s ‘drill, drill, drill’ comments have ‘a lot of merit’

2024-10-31

Kevin O’Leary says Trump knows ‘how the American economy was successful’

2024-10-04

Arlene Dickinson responds to Kevin O'Leary's hot take on Trump tariffs

2025-01-30

Elon Musk in Trump's Cabinet | Kevin O'Leary

2024-08-13

Kevin O'Leary on Trump's tariff threat at World Economic Forum

2025-01-24

'What fraud?': Kevin O'Leary blasts CNN host on Trump civil trial

2024-02-21

Kevin O’Leary: This is the beginning of a giant negotiation

2025-02-11

Trump’s plan to make Canada the 51st state has ‘massive potential’: Kevin O’Leary

2024-12-27

Kevin O'Leary: I advised Trump to ignore them

2025-01-23

Trump meets with Kevin O’Leary and Danielle Smith at Mar-a-Lago #shorts

2025-01-13

Kevin O’Leary SCHOOLS Enraged CNN Panel on Elon Musk, Trump, and Economy

2024-10-28

LILLEY UNLEASHED: Kevin O’Leary on the advantages of a shared currency with U.S.

2025-01-14

Kevin O’Leary: “Trump Win Will Rock Canada, Trudeau Is an ‘Unwanted Mouse’ in the Kitchen’”

2024-11-08

Kevin O'Leary: If anyone can do this, it's Trump

2024-12-20

'Every real estate developer everywhere does this': Kevin O'Leary reacts to Trump civil fraud case

2024-01-12

Kevin O’Leary: Dems are acting like Trump was accused of murder

2024-04-19

Kevin O’Leary Says Democrats ‘Lost Their Way’, Dissects Trump Economics And Investing In Bitcoin

2024-11-12

KEVIN O'LEARY PREVIEWS DONALD TRUMP VS. KAMALA HARRIS!

2024-09-24

Kevin O’Leary reacts to tech CEOs flocking to Trump: 'I'm licking my own chops'

2024-12-18

Kevin O'Leary supports RFK Jr. as Trump's pick for Health and Human Services secretary

2024-11-16

TRUMP WANTS TO BUY CANADA! #shorts

2024-12-26

Kevin O'Leary warns Trump's trial hurts the American brand

2024-05-28

Kevin O’Leary: Tech CEOs ‘sucking up’ to Trump

2024-12-21

Trump's conviction will reduce business investment in US: Kevin O'Leary | Morning in America

2024-06-04

Rick's Rant - Trump and O'Leary

2016-03-09

Trump is his own network: Kevin O’Leary

2024-06-15

Shark Tank Investor Barbara Corcoran On Donald Trump As A Businessman | IGNITION 2018

2018-12-19

Kevin O'Leary Supports Trump's Idea of Canada Becoming The 51st U.S. State, Citing Public Interest

2024-12-28

Kevin O'Leary: This is what Democrats missed in 2024

2024-11-06

Kevin O’Leary reveals who he wants Trump to tap for Treasury secretary

2024-11-18

'GET IT DONE GUY': Kevin O'Leary throws support behind Trump VP contender

2024-06-15

Kevin O'Leary On Trade Impact Towards Canada From President Donald Trump's Tariffs

2018-03-08

Another thing Kevin O’Leary has in common with Trump | 22 Minutes

2017-03-02

Kevin O’Leary: Elon Musk in Trump’s cabinet ‘would be a good thing for everybody in America’

2024-08-13

‘This is an attack on America’: Kevin O’Leary blasts Donald Trump civil fraud penalty

2024-03-21

Kevin O’Leary rips the ‘porn star wars’ against Trump: ‘Complete waste of time’

2024-05-10

Kevin O’Leary: Trump’s bail payment shows ‘the system worked’

2024-04-02