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Why? Because O'Leary is running to lead Canada's Conservative Party until 2019, when he hopes to seek the position of prime minister in the country's general election.
"I'm going to be the leader of the Conservative Party for the next three years," the O'Shares ETFs chairman, told "Fast Money Halftime Report. " "And basically, that gives me a flashlight of transparency to make his life hell."
O'Leary, a Canadian native, said that what inspired him to get politically involved was tied to Trudeau's policy choices and his aversion to newly inaugurated U.S. President Donald Trump. Trudeau, the leader of Canada's Liberal Party, was elected in 2015.
"All [Trudeau's] policies on corporate tax, carbon tax, tax this, tax that, are completely out of sync with the U.S.," O'Leary said. "He should have used the Trump election to basically pivot. He didn't do that."
O'Leary cited a report released by the Canadian Department of Finance as the final impetus for his political pursuit, which projected that the country would run deficits for almost 40 years and end up with $1.5 trillion of debt.
"There's a whole change in the body politic all around the world," O'Leary said. "You saw it in Britain, you saw it in Canada, it certainly happened in the states. People are no longer happy with politicians. They want people that have executional track records."
O'Leary praised Trump's ability to deliver on policy, adding that if he were to work with Trump on the Keystone Pipeline project, the two "could work out a deal in 48 hours on that."
Trump has already begun making policy changes on his first day in office through a series of executive orders.
But despite his praise, O'Leary gave his fans and voters alike a preview of what's to come: "This is going to be 'Shark Tank' versus 'The Apprentice' Smackdown, coming to you in 2020," he said.
Elections for Canada's Conservative Party leadership are scheduled to take place on May 27, 2017. The country's next general elections are scheduled for Oct. 21, 2019.
Disclosure: CNBC owns the exclusive off-network cable rights to "Shark Tank."