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Kevin O'Leary stops for a tea at a Second Cup shop in Burlington, Ont., on April 26, 2017.

Kevin O'Leary's failed Conservative leadership campaign racked up more than half a million dollars in debt, and the TV businessman says he plans on hosting a high-profile fundraiser with NBA owner Mark Cuban in Toronto to pay back his expenses.

According to Elections Canada records, unpaid claims from Mr. O'Leary's campaign total $529,184, with nearly $200,000 coming from the candidate himself.

Mr. O'Leary abruptly dropped out of the contest last May and endorsed Maxime Bernier, who went on to lose the leadership by a razor-thin margin to Andrew Scheer. Mr. Bernier's campaign still owes $275,000, according to the records, although he says he has been fundraising in recent months.

Mr. Scheer only owes about $3,800 to his campaign's accountant, who will be "paid promptly" now that the books are done, campaign manager Hamish Marshall said in an e-mail. The expenses reveal Mr. Scheer paid $226 last May to right-wing Rebel News Network, where Mr. Marshall worked on the campaign during his time in Toronto.

"The campaign once rented a studio from the Rebel in order to shoot videos which appeared on Mr. Scheer's Facebook. The session lasted about 20 minutes. The campaign did not advertise with the Rebel in any way," Mr. Marshall said in an e-mail.

Mr. O'Leary said in an interview he plans on holding a fundraiser in Toronto in April with his American Shark Tank TV co-stars Mark Cuban, a businessman who owns the NBA's Dallas Mavericks, and real estate mogul Barbara Corcoran.

"I asked them, 'Would you come up to Toronto for an evening and help me have a gala fundraiser on April 5,' and they agreed. And that's what I'm working on," Mr. O'Leary said.

"I think together we'll get a broad audience and hopefully have a big event."

He said whatever he raises will go toward paying back vendors – such as photographers, printing services and marketers – before himself.

"I'm not planning on paying anything to myself until the vendors are paid off first."

When asked how he will convince donors to support him again after he dropped out of the race, Mr. O'Leary said he's going to match every dollar and donate it to charity.

"Whatever anybody provides to me, I'll turn around and write a cheque to a charity that supports Canadian entrepreneurs. I don't plan on stopping. If I do it this year and it's successful, I'll do it again next year," he said.

According to Elections Canada rules, candidates can only contribute $25,000 to their own campaigns. But they are allowed to be suppliers to their own campaigns and may use their own funds to pay for personal expenses as long as they are repaid by the campaign within three years of the end of the race. If funds are not repaid within that time, a candidate could face a fine of up to $2,000 and three months in jail, according to Elections Canada.

Mr. Cuban said in an e-mail he is helping Mr. O'Leary fund raise "because he is a good friend." He went on to say "I [don't] know Canadian politics at all," but believes Mr. O'Leary dealing with U.S. President Donald Trump "would be a fun interchange."

Records show Mr. O'Leary spent almost $150,000 on personal expenses. Some of those expenses include high costs for air travel, including individual charges of $31,400, $28,777 and $40,402. Mr. O'Leary said the costs likely refer to aircraft rentals, "because I was going to three cities in one day."

A number of small-business owners and professionals have complained to the O'Leary campaign over their unpaid invoices, given Mr. O'Leary's personal wealth. According to Elections Canada, Mr. O'Leary owes $508.50 to the Cheese Boutique in Toronto, $746.33 to PEI's Upstreet Craft Brewing and $1,330 to a translator in Montreal named Catherine Migeotte, for example.

Mr. O'Leary has been contacting some of his creditors to reassure them they will be paid, telling them he would have already dipped into his pocket if he had the legal right to do so.

Mr. O'Leary said he tried to pay back some of his suppliers through a loan from one of his companies, O'Leary Productions, but said his request was rejected by the Commissioner of Elections Canada, Yves Côté.

"I'm doing everything in my power to clean this up," Mr. O'Leary said. "I have the financial ability to pay it all off now if I could, and I can't."

A photo and video artist who worked on the campaign, and whose firm One2One Photography is owed nearly $6,000, said the problem rests with Elections Canada rules that forbid candidates from repaying their creditors directly.

"I'm very frustrated with the federal system," photographer Pete May said.

Mr. Bernier, meanwhile, said he will be making phone calls to previous donors to his campaign to see whether they want to help him pay down his debt. If he needs to, he will also hold fundraising events in coming weeks.

According to financial records provided to Elections Canada last year, Mr. Bernier owes $250,000 to three companies that offered polling and outreach services to his campaign, in addition to $25,000 to himself. In an interview, he said he has raised about $50,000 in recent months and has deals with the three firms to repay them by next March.

"People who made contributions in the past in support of these ideas, in my view, should be able to help me out to pay down this deficit," said Mr. Bernier, whose campaign raised $2.7-million from nearly 11,000 donors. "I am in politics for the sake of ideas and I will continue to defend them."

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