It was safe to say the Conservative Party's first stint in government hadn't been one for the history books. Although it was still the longest-serving Conservative Minority in history, from Stephen Harper taking the oath of office to him being replaced by Frank McKenna, only 18 months passed. Because of this brevity of Harper's stint in government, few of his cabinet ministers had time to mature into serious national names (perhaps the only one who had was former Minister of Industry Maxime Bernier). Thus, the contenders to replace Harper were not fresh faces (again, Bernier exempted) and instead heavyweights who had been on the political scene a long time. The two candidates thought to have the best chance at winning the race were Jim Prentice, runner-up in the last Progressive Conservative leadership race and former Minister of Indian Affairs and Northern Development, and Jim Flaherty, a Minister of Finance at both the provincial level under Mike Harris and the Federal Level under Stephen Harper. The two came from opposite wings of the party, Prentice being a self-described "Red Tory" and moderate (even voting for same-sex marriage) while Flaherty was very much from the right of the party, being staunchly fiscally (and in some respects even socially) conservative.
Just below Prentice and Flaherty, there was the group of candidates who were thought to have an outside shot at the leadership (who were sometimes mockingly dubbed "contenders for contention"). This group consisted of Stockwell Day, former leader of the Canadian Alliance who had (for the most part) redeemed himself for his past mistakes as Alliance leader in the eyes of the Tory base, Peter MacKay, Minister of Foreign Affairs during the Harper Ministry and the last leader of the Progressive Conservative Party, Rob Nicholson, longtime MP for Niagara Falls and Minister during the Mulroney, Campbell, and Harper governments, and of course Maxime Bernier, MP for Beauce and former Minister of Industry.
Rounding out the field were the longshot candidacies of Josee Verner, Larry Smith, Tony Clement, and Rona Ambrose.
When the Conservative Party membership assembled in Toronto on June 7, 2008 to elect their new leader, conventional wisdom held that Prentice would be able to unite the left of the party better than Flaherty would be able to unite the right of the party due to the higher number of candidates competing for the right-wing vote. Therefore, Prentice was expected to lead on the first few ballots, but there was little consensus on what the size of that lead would be.
As it happened, Prentice's first ballot lead was just over 5%. It was a solid lead to be sure, but it was far from the point where the Prentice camp could be confident that they were favoured; everyone knew the contest was still wide open (although Prentice was perhaps a very slight favourite). The 2nd ballot was more or less a repeat of the 1st, with Prentice again leading by 5% and no major jumps in support for any candidate. The 3rd ballot too much resembled the ballot prior, however, Flaherty was able to pick up votes and cut Prentice's lead to 3% due to support from former Clement voters. On the 4th ballot, things got very interesting. Due to favourable preference flows from former supporters of Larry Smith, Flaherty was able to cut Prentice's lead from 3% to under 0.3%, and on the 5th ballot, due to the flows of former Ambrose supporters, Flaherty was able to take the lead outright, leading Prentice 27%-23%. While Prentice cut into Flaherty's lead on ballots 6 and 7, he was never able to retake the lead, and Flaherty would ultimately take the leadership 55-45 on the 9th ballot.