Why Shark Tank's Kevin O'Leary Has Been Described As The 'Canadian Donald Trump'

One Donald Trump in the world is enough — however, he has a sort of doppelgänger in Kevin O'Leary, a businessman and one of the "Shark Tank" sharks. One of O'Leary's monikers is the "Canadian Donald Trump," and while it's not as fun as his other nickname, "Mr. Wonderful," there are a few reasons O'Leary earned the Trump comparison.

In January 2017, O'Leary announced his plan to run for the Conservative Party leader position in Canada, because he had his eyes on the prime minister seat. On his campaign website, O'Leary said, "I am a successful Canadian businessman with a great deal of international experience." He decried Prime Minister Justin Trudeau for his mishandling of the Canadian economy and mentioned Canada's debt issues. "Now, with the election of Donald Trump to our south, Canada's largest trading partner is headed by a businessman with an aggressive strategy that could hurt the Canadian economy," O'Leary continued. "Trudeau does not stand a chance, and we deserve better."

A more businesslike approach to politics was one major similarity between O'Leary and Trump. That wasn't the only connection between them, however. Neither Trump nor O'Leary had political experience when they ran for office, and they were both on business-based reality shows.

Before his transformation into a politician, Donald Trump was the host of the business-based reality show "The Apprentice" and the seasons branded "The Celebrity Apprentice" (until the last one hosted by Arnold Schwarzenegger). O'Leary is on "Shark Tank" and also appeared in "Dragons' Den," the British show "Shark Tank" was inspired by, and its Canadian incarnation. Mark Burnett created "The Apprentice" and produced both that show and "Shark Tank." 

However, O'Leary and Trump didn't agree on many issues beyond fiscal policies. One major example of this was O'Leary's views on immigration. "I'm a half-Lebanese, half-Irish immigrant," O'Leary told the BBC in 2017. "If there was a wall around Canada, I wouldn't exist. So the policies he is pushing forward are not mine. Canada is a very inclusive country."

O'Leary's political career didn't last long. By April 2017, he was no longer in the running for the Conservative Party leader seat. However, he put his "Canadian Donald Trump" hat back on after the verdict in Trump's civil fraud lawsuit. In February 2024, the judge in Trump's civil case ruled the former president needed to pay $355 million and refrain from business in the state of New York for three years. O'Leary was displeased with that ruling, telling Fox Business that Trump's involvement aside, "There's no rationale for it." He criticized the state of New York, calling it "a loser state." 

In his Fox Business interview, O'Leary explained his rationale. "Forget about Trump, this is not a Trump situation. This is a New York problem now," he said. "Like California is a loser state. There are many loser states because of policy, high taxes, uncompetitive regulation." He claimed he and other businesspeople won't invest in New York anymore, and pitched business ideas that would work better in "winner states."

In an interview with the New York Post about the Trump ruling, O'Leary alleged that every real estate developer would likely be guilty of the same things for which Trump was found guilty. He pointed out that no one seemed to be negatively affected by Trump's actions. "What developer doesn't ask for the highest price valued for any building they built?" he said. He believes the ruling will be appealed and if not, he reiterated how that would make all real estate developers at fault. "It's appalling. It's unjust," O'Leary said of the ruling. "I would go as far to say it's un-American."

Likely furthering the "Canadian Donald Trump" comparisons, Trump took to Truth Social to praise the shark: "Kevin O'Leary is so great, and tells it like it is. Businesses will flee NYC & State after the Corrupt Judge's ruling!" (via Newsweek). However, on a thread on the Politics subreddit discussing O'Leary's reaction, one person quipped, "People who are concerned are only those who have committed the same crimes."