Kevin O'Leary's MAGA Ties Revealed After Criticizing Celebs' Political Opinions

The Shark Tank star and former Conservative Party of Canada leadership candidate is a staunch Trump supporter, despite his criticism of celebrities speaking out on politics.

Published on Feb. 4, 2026

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Canadian businessman and reality TV personality Kevin O'Leary, known for his role on Shark Tank, recently criticized celebrities like Billie Eilish for voicing their political opinions. However, it has been revealed that O'Leary himself is a staunch supporter of former U.S. President Donald Trump and the MAGA movement, despite being a celebrity himself.

Why it matters

O'Leary's criticism of celebrities engaging in politics is seen as hypocritical, given his own failed bid to lead the Conservative Party of Canada and his vocal support for Trump's policies. This highlights the complex relationship between celebrity, politics, and public perception.

The details

In a recent appearance on Fox News, O'Leary criticized singer Billie Eilish for using her Grammy acceptance speech to protest U.S. immigration policies. O'Leary claimed that Eilish's comments had 'torched' her, suggesting that celebrities should 'shut your mouth and just entertain.' However, O'Leary himself is a celebrity who previously ran for the leadership of the Conservative Party of Canada in 2017, openly comparing himself to Trump and promising to 'beat Justin Trudeau and bring back jobs to this country.' Despite not gaining enough support to win the leadership race, O'Leary has remained a vocal supporter of Trump and the MAGA movement.

  • On February 3, 2026, Kevin O'Leary appeared on Fox News and criticized celebrities like Billie Eilish for sharing their political opinions.
  • In January 2017, O'Leary announced his bid for the leadership of the Conservative Party of Canada, comparing himself to Donald Trump.

The players

Kevin O'Leary

A Canadian businessman and reality TV personality, known for his role as an investor on the show Shark Tank. He previously ran for the leadership of the Conservative Party of Canada in 2017, openly supporting Donald Trump and the MAGA movement.

Billie Eilish

An American singer-songwriter who won the Grammy Award for Song of the Year in 2026 for her song 'Wildflower.' During her acceptance speech, she used the platform to protest U.S. immigration policies, which triggered a response from O'Leary.

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What they’re saying

“As grateful as I feel, I honestly don't feel like I need to say anything but that no one is illegal on stolen land. And, yeah, it's just really hard to know what to say and what to do right now, and I feel really hopeful in this room, and I feel like we just need to keep fighting and speaking up and protesting, and our voices really do matter, and the people matter, and f--k ICE. That's all I'm going to say. Sorry. Thank you so much.”

— Billie Eilish (Variety)

“I feel sorry for celebrities that wander into this kind of thing without doing at least a basic AI search. She got torched.”

— Kevin O'Leary (Fox News)

“There's a kernel of an idea sparked by this massive narrative that occurred, just at a flippant statement at the Grammys. I'm very optimistic that from this, something good will happen. As far as Billie, I say this to entertainers: Half the people in politics that you piss off won't buy your music anymore. Don't be stupid about it. ... It's the first lesson 101 for celebrity. As you rise up, whether you're a film star, a music star, or whatever, shut your mouth and just entertain.”

— Kevin O'Leary (Fox News)

The takeaway

Kevin O'Leary's criticism of celebrities sharing their political opinions is seen as hypocritical, given his own history of political involvement and support for the MAGA movement. This highlights the complex and often contradictory relationship between celebrity, politics, and public perception.