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

At 6:45 a.m. on Wednesday, Kevin O'Leary was already on the road to Hamilton, Ont., in a black rental Chrysler sedan driven by one of his young campaign staffers. "We have to scrimp and save," Mr. O'Leary said dryly, as he buckled himself into the front seat.

The would-be leader of the Conservative Party of Canada had a busy day ahead of him: an early morning meet-and-greet with supporters, a luncheon with the Spadina-Fort York Conservative Association, a fundraiser at the private Albany Club in Toronto, and of course, the final leadership debate. Plus, the celebrity investor was taking business calls on the side, answering questions about the European markets from the highway.

Dressed in his signature black suit and tailored shirt, Mr. O'Leary seemed upbeat, but tired. It turned out later he had had a late night.

John Ibbitson: Before Conservatives elect Maxime Bernier, they should consider this

Mr. O'Leary was about to head into the final month of the Conservative leadership race, and the slog wasn't slowing down. The party had just released its final membership list, and at 259,000, it was much higher than Mr. O'Leary had expected, meaning he'd have to work even harder to reach new members across the country.

"It's like a roadshow," Mr. O'Leary said, referring to the investment term for presentations to potential buyers, "except it never ends."

At that moment, it turns out, it was already over.

The Globe and Mail was supposed to shadow Mr. O'Leary for the day, following him to events in order to gauge his support and understand his strategy in winning the leadership. Instead, by late morning he revealed he was going to quit, citing lack of support in Quebec, and endorsed one-time rival Maxime Bernier. Most of his campaign team only found out after.

In a late-night meeting on Tuesday that stretched into early morning, Mr. O'Leary met with Mr. Bernier at a private residence in Toronto, according to the two campaigns, and then with leadership candidate Andrew Scheer at the Novotel hotel downtown. It is unclear why he met with Mr. Scheer after his meeting with Mr. Bernier, or which of them set it up. Mr. O'Leary's campaign said Mr. Scheer called Mr. O'Leary and asked to meet, but Mr. O'Leary could only do so after meeting with Mr. Bernier; Mr. Scheer's campaign said Mr. O'Leary made an "overture" to meet, but it became clear he had already made a deal with someone else.

While the move has solidified Mr. Bernier as the front-runner in the lead-up to the May 27 leadership contest, it is not a guarantee he will win. He and his libertarian policies are now the main targets in the race, and other candidates have already said they are going after Mr. O'Leary's supporters. "His people are up for grabs," leadership candidate Erin O'Toole said Wednesday night following the debate.

Mr. O'Leary and Mr. Bernier's senior advisers, Mike Coates and Kory Teneycke, have already joined forces, and drove back to Ottawa together on Thursday. While Mr. Coates, the campaign chair, said he believed much of Mr. O'Leary's team will move to the Bernier camp, not everyone is happy.

A long-time Conservative strategist who joined Mr. O'Leary's team in the early days of his candidacy said that "a lot of people on the campaign are bitter." He said some of the top organizers on the campaign are calling around to apologize to the Conservative members whom they convinced to support Mr. O'Leary, explaining that the candidate never gave his all to winning the race.

"He didn't understand what the job entailed," the strategist said. "I'll never again work on a campaign for someone who has no political experience and doesn't know what he is getting into."

In the car ride on Wednesday back into Toronto, Mr. O'Leary told a story about running into fellow candidate Kellie Leitch at a Tim Hortons in Portage la Prairie, Man. "There's a place you've never heard of," Mr. O'Leary said.

Mr. Coates said the campaign first "began to struggle" with Mr. O'Leary this month, "to do the things that the candidates always have to do in order to be elected."

"It's a grind, and it's one of the things that you have to admire about our candidates. I mean, they are working very hard to meet people and win them over, and that involves a lot of rubber chicken," Mr. Coates said.

He said Mr. O'Leary first revealed his hesitations with members of his senior team last Thursday over beers on the rooftop bar at The Porch, a pub in downtown Toronto close to the campaign headquarters.

"I think we had him convinced that he could win the leadership, but he was really getting worried about the run for prime minister," Mr. Coates said.

"We thought that given two years, he could make inroads in Quebec as well. He didn't buy that."

Mr. O'Leary consulted his family and by the end of the weekend, had made his decision. "It became very clear to us on Monday … that he was more comfortable with pulling out than staying in," Mr. Coates said.

Senior officials from both camps helped to facilitate the meeting between Mr. Bernier and Mr. O'Leary, with Mr. Teneycke providing Mr. Coates with Mr. Bernier's cellphone number for Mr. O'Leary to call and arrange a meeting.

Mr. O'Leary's team also said the ballots were mailed out earlier than expected, leading Mr. O'Leary to speed up his announcement. Conservative spokesman Cory Hann said that according to party rules, the ballots were to be mailed out by Friday.

At his meet-and-greet event in Hamilton early Wednesday, Mr. O'Leary didn't tell the crowd he was dropping out. But he left subtle hints.

"Who is the person that can win? It's not just about becoming the leader of the party, it's who can actually win," he said.

He told the crowd the leader has to speak French in order to get 30 seats in Quebec. He said he was in an immersion course with his wife, before testing out some lines on the audience. "Getting there, getting there. But not there yet," he said.

Later, at a press conference with Mr. Bernier, Mr. O'Leary said he can use his significant media outreach to bring young members to the party.

He defended the time he spent in the United States during the campaign, saying he uses his television platform to defend Canada's interests.

"I'm a very well-known Canadian to Americans," he said.

And on Thursday, he was back on TV – from New York.

With a report from Daniel Leblanc

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