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Win
Kevin O'LearyKevin O'Leary

WeWork is a disaster that will inevitably go to zero.

You are a zero and you're going to zero with a bullet... It always goes to zero because what you're basically doing is taking long-term debt obligations to either lease or buy a building and then you're providing short-term leases to some really shitty companies that don't make any money... It is a disaster on wheels.

WeWork eventually filed for bankruptcy in 2023 after its valuation crashed from $47 billion to essentially zero.
Loss
Kevin O'LearyKevin O'Leary

Justin Trudeau is a poor leader who should not be managing Canada because he has never run a business.

Justin Trudeau is that he's never run a business yet has no idea what he's doing when it comes to being competitive... Trump slaughtered him on energy just yesterday. Another seven billion dollars left Canada in the energy space and it's moving to the US... I like Justin as a person. I would never let him manage my money. He shouldn't be managing a country and he will lose his job soon because Canadians are just howling at the moon there.

While O'Leary's economic critiques are subjective, his prediction that Trudeau would lose his job 'soon' was incorrect, as Trudeau remained Prime Minister through the 2021 election and beyond.
Void
Kevin O'LearyKevin O'Leary

I can sense the 'aura of success' or failure in a person before they even speak.

I can actually tell now when they step out on that carpet... and at that moment I can sense their aura. And I know exactly whether we have winners or losers. They don't even have to say anything. I'm right a hundred percent. I can now at this point sense the aura of success or losers.

This is an unverifiable claim about his own perception.
Win
Kevin O'LearyKevin O'Leary

Jimmy Garoppolo is not a championship-caliber quarterback because he missed the throw to Emmanuel Sanders.

I'm taking 20 percent off retail on [Jimmy Garoppolo]. He did not perform. He had a minute and a half, I said, 'this is his moment to shine.' He did nothing... he missed that throw to Emmanuel Sanders. That was it. You can't be forgiven for that.

Garoppolo never won a Super Bowl as a starter and was eventually replaced in San Francisco.

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