Inside the 'moment of truth' for Kevin O'Leary's campaign

Three key members of Kevin O'Leary's leadership team sat down with him last Thursday on a patio near his campaign office and cracked open a beer. They had a pointed question to pose that would have been unthinkable when they risked all and tossed in their lot with the Conservative outsider. 

​"We began to see over the course of the months just somewhat of a change in him," said Mike Coates, the chair of O'Leary's campaign. Campaign manager Chris Rougier and strategist Andrew Boddington were also at the meeting

"Last Thursday we said, 'Is your heart in this? Are you having second thoughts?'"

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Coates told CBC News that he still believed O'Leary could win the leadership race and the next election. But he wasn't the candidate. O'Leary had doubts and those doubts were now crippling. 

"It was a moment of truth," said Coates.

Private meeting

But Coates said he wasn't truly sure his candidate was out of the race until O'Leary met one on one with Maxime Bernier late Tuesday night in Toronto.

The conversation started around 11 p.m. and went on for two or three hours

That conversation ended O'Leary's candidacy.

There were no "serious" discussions with any other campaign, Coates insisted. The only two options they seriously considered were dropping out without an endorsement or endorsing Bernier, whom the campaign also saw as something of an outsider or a disrupter within the party. 

Still, Coates said, he wishes O'Leary had hung in.

"Of course, we tried to convince him because we were in this to win. All I can say is he came to a different view, and he's the guy with his name on the ballot, and he's a pretty good little strategist himself.  For him it's always been about beating Trudeau, and this is the way he felt he could do that the best."

Stomach for the job?

But the pugnacious reality TV personality had other reasons for abandoning the race.

A senior member of O'Leary's team said the businessman took a hard look at what would be needed to rebuild the Conservative Party and decided he and his family didn't have the stomach for it.

That effort would have meant weekends away from his family and time away from the posh boardrooms and bustling television network studios in the United States. Rather than spending time in San Francisco and South Beach, he would be compelled to shake hands in Summerside, Sarnia and Saskatoon while meeting individual Conservatives in legion halls and church basements.  

That dimmed his ardour for the job.

Another source said there were concerns about the number of new members the Conservatives had signed up. The path to victory O'Leary's team had envisioned involved roughly 200,000 Conservative Party members. When the party announced that thanks to the leadership race it now had nearly 260,000 members, the O'Leary campaign wasn't certain where the additional support came from and how it would affect their chances.

What's next?

O'Leary's team isn't counting on all its supporters rallying behind Bernier, but hopes that if a sizable chunk — perhaps a third — make the switch, Bernier could pull off a first ballot win, said a member of O'Leary's team.

As for O'Leary himself, he's publicly pledged to campaign with Bernier. 

Coates believes the businessman's social media and fundraising savvy could also be used to help grow the Conservative Party.

But will O'Leary stick around?

"I hope so," said Coates.