'He Saved My Ass,' Says Teary-Eyed Kevin O'Leary About The Time Mark Cuban Helped Him Out As He Was '$2 Million In The Hole'

In a recent heartfelt interview, Shark Tank star Kevin O’Leary opened up about when Mark Cuban, his fellow shark, stepped up for him in a tough spot. In an exclusive sneak peek from O’Leary’s appearance on Who’s Talking to Chris Wallace?, the usually tough-talking “Mr. Wonderful” showed his emotional side as he recalled how Cuban flew in to help him when he was in deep financial trouble.

People reports that the story goes back to 2017 when O’Leary decided to run for leadership of Canada’s Conservative Party. Things were going fine initially; he felt confident and was leading the polls. However, the effort encountered a significant obstacle in Quebec. 

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O’Leary admitted he had difficulty speaking French, a critical skill for winning over Quebec voters. “I’m dyslexic, I’ll never learn French,” O’Leary explained. Eventually, he decided to drop out of the race, but not without consequences.

Here's where things got sticky: Canadian campaign laws meant that if you lost, you had to pay back your campaign debts, but you could only do it through contributions from Canadian citizens – with a cap of $1,600 per person. 

O’Leary was $2 million in the hole and the rules wouldn’t allow him to pay it off himself. “I wanted to write the check and just clear the books and the government said, ‘No, you can’t do that. You’re going to be subject to the laws of the land,'” he said.

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In this tough situation, O’Leary called the one person he thought could help: Mark Cuban. He said, “Mark, I’m in trouble here. I need to hold an event where I can sell a lot of tickets to a lot of people who are going to attend and I need you to fly up here and be beside me on the stage,” O’Leary recalled.

Without missing a beat, Cuban was ready to help. He was on the plane the next day and never even questioned it, saying, "Where do I have to be? I’ll be there."

The memory struck a chord with O’Leary, as he needed to take a moment to collect himself during the interview. He took a sip of water and admitted that he owed Cuban a lot for that and that he “saved my ass.” It was a rare look at O’Leary’s more compassionate side. On Shark Tank and elsewhere, he’s frequently seen slugging it out with Cuban and playing up their rivalry for the cameras.

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