"I owe him a lot" — When Shark Tank mentor Kevin O'Leary recalled Mark Cuban's support during a political setback

Kevin O’Leary, a well-known investor from Shark Tank, recently opened up about a pivotal moment in his life when fellow Shark Tank star Mark Cuban stepped up to help him during a difficult time.

In an exclusive interview with People, published on October 17, 2024, O’Leary became emotional as he recounted the support he received from Cuban during his 2017 political campaign for the leadership of Canada’s Conservative Party.

"Anyways, I owe him a lot for that. He saved my a*s," Kevin O'Leary said

The interview was part of his appearance on Who’s Talking to Chris Wallace?, streaming on Max. O’Leary’s campaign came to an abrupt halt when he faced challenges due to his inability to speak French fluently, forcing him to withdraw.

This left him with a $2 million debt, as Canadian laws require political candidates to repay their campaign debts within two years to avoid legal repercussions.

Seeking assistance, O’Leary reached out to Cuban, who immediately agreed to help by participating in a fundraising event.

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Shark Tank mentor Mark Cuban’s immediate support for Kevin O'Leary

During his appearance on Who’s Talking to Chris Wallace?, Kevin O’Leary opened up about the financial challenges he faced after withdrawing from the 2017 Conservative Party leadership race in Canada. The campaign, which required candidates to repay debts within 24 months, left O’Leary with a $2 million shortfall.

With the clock ticking and legal repercussions looming, O’Leary sought assistance from Mark Cuban, his co-star on Shark Tank. O’Leary recounted how he called Cuban, explaining his dire situation and asking for help to organize a fundraising event in Toronto. Cuban agreed without hesitation, as O’Leary mentioned:

"He never even questioned it. He said, 'Where do I have to be? I'll be there,'"He was on the plane the next day," O’Leary recalled emotionally during the interview.

O'Leary mentioned that he had been significantly leading in the polls during his campaign until he faced challenges in Quebec due to his dyslexia, which made it difficult for him to learn French.

He added that this experience tied into a significant story about Mark Cuban, highlighting their friendship despite often being portrayed as competitors.

The fundraising event was a success, with Cuban’s presence attracting a large crowd that helped O’Leary raise the necessary funds to clear his campaign debts. O’Leary expressed his appreciation for Cuban’s selflessness, noting that this act of kindness went beyond their professional relationship.

O’Leary credited Cuban with helping him through one of the toughest periods of his life.

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Kevin O'Leary and Mark Cuban's friendship

On Shark Tank, Kevin O’Leary and Mark Cuban are often seen as opposites. One memorable moment on the show that showcased their dynamic occurred during a pitch. While the two disagreed on the valuation, Cuban surprised everyone by stepping back and letting O’Leary take the deal.

Beyond the competitive environment of Shark Tank, their relationship has been marked by moments of genuine camaraderie. In a 2014 episode, both O’Leary and Cuban jointly invested $150,000 for a 10% equity stake each in Bottle Breacher, a company founded by military veteran Eli Crane that turns decommissioned bullets into bottle openers.

Off-camera, their relationship deepened through moments like Cuban stepping in to help O’Leary during his 2017 financial struggles. O'Leary and Cuban have been mentors on ABC's Shark Tank since its third season, which premiered in 2012.

They are joined by fellow long-time cast members Daymond John, Barbara Corcoran, Robert Herjavec, and Lori Greiner.

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