2006 federal Liberal leadership race
On April 5, 2006 Kennedy resigned as Minister of Education to pursue the federal Liberal Leadership. Premier McGuinty, who admitted that finding a replacement was difficult, was reported to have set that day as a deadline for Kennedy to make a decision in order to prevent the leadership speculation from overshadowing the Ontario government's agenda. Kennedy formally declared his candidacy in front of the House of Commons in Ottawa, on April 27, 2006.
On May 18, Kennedy formally resigned from the provincial legislature. His resignation came after several weeks of criticism over drawing an MPP's salary, despite his absence from the legislature and his stated intention to live for part of the summer in Quebec. Kennedy responded saying that he intended to resign his seat "sooner rather than later," but first wanted to finish some local projects he'd been working on.
On August 16, Premier McGuinty called a by-election to replace Kennedy in Parkdale–High Park for September 14. The centre-left leaning riding was arguably held in part thanks to Kennedy's personal popularity (due to his work as food bank director and education minister) versus that of his party; Sylvia Watson could not retain the seat for the Liberals in the subsequent by-election, apparently being unable to "ride the coattails of Kennedy's popularity".
The Toronto Star reported that Gerard Kennedy appeared to have signed up more new members than any other candidate during the member recruitment period. The article stated that it had been "conventional wisdom" that Michael Ignatieff and Bob Rae were the leaders in the race but Kennedy's numbers indicated that it was a wide-open race.
On September 8, Joe Fontana, MP for London North Centre and Gerard Kennedy's Ontario Co-Chair, announced that he would be resigning his seat in the House of Commons to run for mayor in London; and, it was speculated Kennedy would run in the by-election, which he did not.
On "Super Weekend", from September 29 to October 1, the Liberal Party elected approximately 85% of delegates. Kennedy finished in third place with 17.3% of delegates being pledged to his campaign, a similar number to Stéphane Dion, who received 16.0% and to Bob Rae who received 20.3%. Besides sizable delegate support he was supported also by 20 MPs and former MPs, with about a dozen Ontario MPPs.
On November 27, Kennedy attracted media attention when he became the first leadership candidate to oppose a motion being debated in the House of Commons of Canada, that would have declared the Québécois "a nation within a united Canada". Kennedy was joined in that position later that day by fellow candidates Ken Dryden and Joe Volpe.
At the convention, Dion placed higher than Kennedy in the first ballot voting, finishing ahead of Kennedy by two votes–17.8% to 17.7%). That gap increased to 2% after the second ballot–20.8% to 18.8%. Kennedy chose to leave the ballot before he would have been forced to, and supported Dion. Earlier, the two leadership contenders had allegedly struck a pact in which the first off the ballot would throw his support to the other. Pundits said that this surprise move had caught the Ignatieff and Rae strategists off guard. Kennedy delivered his delegates extraordinarily en masse, as Dion's support increased to 37.0% on the third ballot, moving from third place to first and eliminating Rae. Dion retained the position for the fourth and decisive ballot which resulted in him winning the leadership.
