Kevin O’Leary Sheds Tears as He Recalls How Mark Cuban ‘Saved’ Him From $2 Million Debt

“He didn’t even blink. He was on the plane the next day. He never even questioned it,” the investor tells Chris Wallace

Kevin O'Leary on "Who's Talking to Chris Wallace" (CNN, Max)
Kevin O'Leary on "Who's Talking to Chris Wallace" (CNN, Max)

Kevin O’Leary shedded tears sharing an anecdote about a time when his “Shark Tank” co-star Mark Cuban “saved” him from potentially spending time in prison over a $2 million debt.

“I owe hime a lot. He saved my ass,” O’Leary told Chris Wallace on the journalist’s CNN Max-based series “Who’s Talking to Chris Wallace.” At the time Wallace inquired about O’Leary’s stint in Canadian politics.

“In 2017 you were running to be the head of the Conservative Party, and you dropped out at the last minute because you didn’t speak French well enough,” Wallace stated.

That’s when O’Leary detailed how his campaign ultimately left him with a couple million in debt after losing in his run.

“I was leading in the polls, dramatically, until I hit Quebec. I’m dyslexic, I’ll never learn French. And it also leads to a story about Mark Cuban that is very important when people pit us against each other, a lot,” O’Leary explained. “In the Canadian system, you have to pay back your losses if, if you’re a loser in a race at $1,600 per contribution by only Canadian citizens, you can’t pay back your own debt, and if you fail to do it in 24 months, you can be put in prison. I was $2 million in the hole, and 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.’”

O’Leary went on to say that’s when he decided to phone Cuban to ask him for help.

“I called up Mark. I 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.’ He didn’t even blink. He was on the plane the next day. He never even questioned it. He said, ‘Where do I have to be? I’ll be there. So …”O’Leary said, pausing before tears as tears began to fall.

“Give me a moment,” O’Leary says trying to collect his emotions.

Wallace chimed in as O’Leary collected himself saying: “Well, I did not have that on my bingo card, Mr. Wonderful, uh, getting emotional.”

“Anyways, I owe him a lot. He saved my ass,” O’Leary said as he pulled himself together and dried his eyes.

Getting back to business, the investor also shared his thoughts on who he feels, between Vice President Kamala Harris and former President Donald Trump, would “create a better economy” over the next four years. He said he knows Trump’s policies but not Harris’.

“My big beef, I don’t know Harris’s policies,” he explained to Wallace. “She won’t sit down to discuss anything about price gouging in detail, or corporate taxes, or any of this. So of course, I’m critical. I’m very critical. She’s all sugar, no protein, that’s what I hear.”

And as for Trump, O’Leary said he’s fully aware of what Trump brings to the table, despite Trump’s controversial past.

“I know his policies. He ran the economy for four years. You may not like him, you may hate him, and I know that half the country hates him, but I know what I got,” O’Leary continued. “I know what I got on regulation. I know what I got on taxes. I know what I got on energy. I know what I got in foreign policy. I know the devil that I know, if you want to call him that, so if that’s all you’re offering me is the Trump that I know, or the unknown, crazy stuff, I’ll take the known.”

While it’s not often, O’Leary, or Mr. Wonderful as he likes to be called, doesn’t hide from his emotions, whether they’re tears or frustrating outbursts on “Shark Tank.” The original shark and Cuban will make their return the business and entrepreneurship series in Season 16 starting Friday on ABC. This will be Cuban’s last season.

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