You see him on Shark Tank tearing into a founder about customer acquisition costs, but lately, Kevin O’Leary is spending more time on cable news talking about the 45th and 47th President. It’s a weird dynamic. Some call him a "MAGA shill," while others think he’s just a pragmatist looking at a spreadsheet. Honestly, the reality is a lot messier than a 30-second soundbite.
Basically, the relationship between kevin o leary trump isn't just about two reality TV stars who like the sound of their own voices. It's a calculation. O’Leary has spent the last year—specifically as we’ve rolled into 2026—positioning himself as a sort of unofficial economic translator for the Trump administration. He’s the guy who goes on Fox Business or CNN to explain why a specific policy might work, even when he’s privately (and sometimes publicly) ripping the details to shreds.
The "51st State" Drama and the Mar-a-Lago Pilgrimage
If you want to know how deep this goes, look at the end of 2024. Trump made one of his classic bombastic "jokes" about Canada becoming the 51st state. Most Canadians were, understandably, pretty ticked off. But O’Leary? He leaned in. He started talking about an "economic union."
He even claimed on Varney & Co. that half of Canada was interested. Pro tip: they weren’t. Polls showed maybe 13% of people liked the idea.
O’Leary didn't care about the polls. He announced he was heading down to Mar-a-Lago to talk "shop" with the President-elect. Critics like Nelson Wiseman, a political science professor at the University of Toronto, pointed out that O’Leary wasn't actually trying to hand over Canadian sovereignty. He was pushing for a customs union—something similar to the EU. He wanted a shared currency and a shared passport. It’s a massive, radical idea that basically no one in the Canadian government wants, but it kept O’Leary in the room where it happens.
Why the "Mr. Wonderful" Label Fails Here
A lot of people think O’Leary is just a Trump clone. That’s lazy. O’Leary didn't get into politics for the "movement." He got into it because he thinks the world is one big balance sheet. When Trump won in November 2024, O’Leary went on Fox Business and literally said Trump "saved entrepreneurship."
He argued that the 21% corporate tax rate was the only thing keeping capital in the U.S. and that a Harris victory would have "broken the American model."
But don't think he's a total devotee.
He’s been incredibly vocal about things he hates. When Trump floated the idea of the government taking a 10% stake in Intel, O’Leary went nuclear. He called it "abhorrent" and a "really, really bad idea." He doesn't believe in "nationalizing" anything. To him, if a company like Intel is failing, it should "die like a slug at the bottom of the ocean." Brutal? Yeah. But it shows that his loyalty isn't to Trump—it's to his own brand of ruthless capitalism.
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The 2026 Reality Check: Tariffs and the Midterm Push
As we sit here in early 2026, the honeymoon phase of the second Trump term is hitting some serious turbulence. O’Leary is out there right now flagging some major red flags.
The big one? Tariffs.
Trump loves them. O’Leary is terrified of what they’re doing to the little guy. He’s been pointing out that duties on things like potash, bauxite, and softwood lumber are driving up the cost of building houses and buying food. He’s calling it an "underappreciated driver of inflation."
- Small Business Stagnation: O’Leary is sounding the alarm on a hiring freeze. December 2025 saw only 50,000 jobs added. That's a disaster.
- The IRS War: He’s been railing against the "big, ugly" tax bills that give the IRS more power to audit small businesses. He calls it a "war on small business."
- The "Shill" Accusation: On X (formerly Twitter), O’Leary recently posted: "I don’t shill for politicians, but I shill for policy."
He’s clearly trying to distance himself from the political fallout while still staying close to the power. It’s a delicate dance. He knows that 72% of jobs in America come from companies with fewer than 500 employees. If Trump’s policies crush those businesses, O’Leary’s "entrepreneurship" brand goes down with the ship.
What Really Happened with the New York Fraud Case?
You might remember back in 2024 when Trump was facing that massive civil fraud judgment in New York. O’Leary was the loudest voice in the room defending him. Not necessarily because he liked Trump, but because he was scared for his own portfolio.
He argued that seizing Trump’s assets "tainted the American brand." He told anyone who would listen that if New York could do that to a former President, they could do it to any investor. He even threatened to stop investing in New York entirely, calling it a "loser state."
This wasn't just talk. It was a calculated move to position himself as the defender of property rights. He saw the legal battle not through a lens of justice or crime, but as a "breach of contract" issue that would scare off foreign capital. Whether you agree with him or not, it worked—it made him a hero in the MAGA ecosystem and a villain to everyone else.
The Contrast in 2026
Now, in 2026, the tone has shifted. The rhetoric is less about "defending the brand" and more about survival. With the midterms approaching, O’Leary is warning the administration that they can’t just rely on "optimistic messaging."
He’s looking at the Supreme Court right now, waiting for rulings on tariff rebates. He’s looking at the job numbers. He’s essentially telling the White House: "The spreadsheet doesn't lie, and right now, the numbers are turning red."
How to Navigate This as an Investor
If you're following the kevin o leary trump saga to figure out where to put your money, you have to look past the TV drama. O’Leary’s actual investment moves are telling a different story than his Fox News appearances.
He’s pivoting.
Right now, he’s heavily pushing private real estate and energy infrastructure. Why? Because he thinks the public markets are too tied to the "noise" of Trump’s tweets and the "signal" of the Federal Reserve’s interest rate battles. He’s obsessed with the fact that China is out-building the U.S. in power generation by 4x.
To follow his lead, you'd look at:
- Energy Independence: Infrastructure that bypasses the "gridlock" of traditional utilities.
- Hard Assets: Moving away from tech giants like Intel (which he thinks is "a dog") and toward things that people actually need to survive—housing and food supply chains.
- Policy Hedging: Don't bet on the "big beautiful bill" passing in its current form. O’Leary expects the "ugly" parts (the IRS audits and small business taxes) to get shredded before July 4th.
The takeaway here is pretty simple. Kevin O'Leary isn't a Trump supporter in the traditional sense. He's a guy who views the presidency as a CEO role. When the CEO does something that helps the stock price (deregulation, tax cuts), O'Leary cheers. When the CEO does something that hurts the bottom line (tariffs, government overreach), he boos.
Keep your eye on the job reports and the tariff rebates. If O'Leary starts getting even louder about "policy uncertainty," it’s a sign that the business community is losing patience. Watch the data, ignore the hair, and remember that in O'Leary's world, the only thing that matters is whether the check clears.
Next Steps for You:
If you want to track this yourself, monitor the NFIB Small Business Optimism Index alongside the 2026 midterm polling. When O'Leary talks about "policy uncertainty," he's usually looking at the delta between those two numbers. If optimism drops while the GOP's lead shrinks, expect a massive pivot in his rhetoric by the summer.