Kevin O'Leary is a businessman who loves a good deal, but his attempt to sell the Commissioner of Canada Elections on his pitch to pay off campaign creditors seems to have flopped.

CBC News first reported that after the reality TV star shocked the political world by dropping out of the Conservative leadership race, his campaign was saddled with more than $200,000 in debt.

Now, in a letter O'Leary shared with CBC News, lawyers for his production company peg the debt at $300,000.

In fact, it seems the three biggest fundraisers in the Conservative leadership race are also the three with outstanding debts.

The campaigns of Maxime Bernier, Kellie Leitch and O'Leary all said they are in the red, though Leitch's campaign said the debt was minor. All of the 11 other campaigns said that, while they were awaiting final numbers, they believed they would break even or have a surplus. Brad Trost's campaign said it was uncertain, but that a small deficit was possible.

O'Leary's pitch fails

While O'Leary has not shied away from touting his own financial success, he's not allowed to pay back his campaign debts himself.

The Canada Elections Act says an individual candidate can't donate more than $25,000 in contributions, loans and loan guarantees to his or her campaign. The limits are there to keep wealthy candidates from having an unfair advantage.

But O'Leary wanted the commissioner to let him bend — perhaps even break— the rules.

The law firm that represents O'Leary Productions made its pitch to the Commissioner of Canada Elections in a letter dated May 23. That's four days after CBC News first reported that O'Leary's campaign was in debt, and that some campaign contractors were complaining about unpaid bills.

The law firm's letter asks that the production company be permitted to loan O'Leary's campaign $300,000 "to facilitate the payment of small vendors who may face financial hardship as a result of having their accounts to the campaign go unpaid for a prolonged period of time."

While the letter refers three times to the potential suffering of small vendors, it also notes that if O'Leary Productions can't loan the campaign the money, O'Leary himself could be squeezed by potential legal action.

"The litigation could very well result in Mr. O'Leary being required to pay these accounts directly if he is found to be personally liable for them," the letter reads.

It also calls the proposed loan "an option of last resort" and notes that "attempts to secure loans from banks have been unsuccessful."

O'Leary told CBC News his pitch was rejected.

"They said no. I think a candidate should be personally liable for any debts not cleared after the race is over and the outcome has been determined. This law seems unfair to smaller vendors that service the political process in Canada that get hung out to dry waiting while the candidates try to raise dollars for a race that is already over," he said.

O'Leary must now repay his leadership debt by soliciting individual Canadians to donate a maximum of $1,550 each until he has enough to cover his outstanding costs.

Bernier's debt tied to O'Leary

In Bernier's case, it seems his campaign debt is at least in part due to his dealings with O'Leary. When the businessman and reality TV star dropped out of the race, Bernier not only accepted O'Leary's endorsement, he also agreed to hire scores of O'Leary's campaign staff for the final leg of the campaign.

A spokesperson for Bernier said his campaign was still waiting for some bills to come in but would "certainly" have a deficit, though she could not provide a precise figure.

Bernier was the top fundraiser in the Conservative race, bringing in more than $2 million, according to filings with Elections Canada. (Final fundraising totals haven't yet been made public.)

O'Leary raised more than a $1 million during his short time in the race.

Leitch's campaign, driven by a promise to screen immigrants, refugees and visitors for what she called "Canadian values," raised more than $1.3 million. Leitch's deficit would be "small," said spokesperson Michael Diamond.

"We are very confident that we will be able to raise sufficient funds in very short order."