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When the Conservative Party convenes in Toronto this weekend to choose its new leader, the person many thought the most likely to win will instead be where he is most comfortable: sitting on a media panel, performing for the cameras.

Kevin O’Leary was the frontrunner in the race to succeed Stephen Harper. Victory was within reach when, just weeks before the convention and with ballots with his name on them already arriving in voters’ mailboxes, he made the sudden decision to pull out of the race. As the person who chaired Kevin’s campaign, I’ve had more than a few questions about what happened. And while there has been much speculation about why he quit, at the end of the day it came down to one thing: he was never fully committed.

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My journey with O’Leary began with a brief phone call at the end of November. I had never met the businessman-turned-reality TV star, but after months of rumours about his candidacy — rumours he had instigated and happily fuelled — Kevin was now looking for someone to actually lead his campaign. A mutual friend had passed along my name. After only a brief discussion, he asked me, “Will you be my guy?” It made me laugh, because it sounded like he was asking for a date. I suggested we should meet first, “so we can decide if we like each other.”