Kennedy previously ran for the leadership of the Ontario Liberal Party, losing to future premier Dalton McGuinty on the final ballot.

He finished third in delegate selection meetings, but at the leadership convention, he placed fourth on both the first and second ballot before withdrawing to support the eventual winner, Stéphane Dion.

[3][4] Kennedy's father, descendant from Scottish ancestry originating in Cape Breton Island and the Ottawa Valley, ran a gas supply business in The Pas, Manitoba, eventually becoming that town's mayor.

[4][5] When Trent's hockey program was cancelled, Kennedy switched education institutions and attended the University of Alberta to continue his undergraduate studies, but left in his fourth year, without completing his degree.

[10] Despite being a newcomer to politics, Kennedy became the front-runner to replace Lyn McLeod as leader of the Ontario Liberal Party in late 1996.

[11] Although popular on the left-wing, he encountered a strong "anyone-but-Kennedy" movement from the party's establishment and right-wing which was divided among several candidates on the leadership convention floor.

[17] Media reportage at the time anticipated that this would be a close race, due to the perceived relative strength of the three main parties being almost equally divided in this newly constituted constituency.

[21] 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.

[24] 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.

[27] 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".

[37] 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.

In late August 2007, Kennedy entered the academic world accepting a position at the Ted Rogers School of Management at Ryerson University.

[7] In late September 2007, Kennedy was part of a group observing Ukraine's parliamentary elections in the Mariupol electoral commission.

Kennedy reported back to the Canadian media that the group he was a party to was confronted by Ukrainian police who stripped passports and observer statuses.

[41] On March 31, 2008, although he was not a member of the House of Commons of Canada, Kennedy was appointed to the Official Opposition Shadow Cabinet by leader Stéphane Dion.

Kennedy served as Intergovernmental Affairs critic, which gave him responsibility to speak on behalf of the Liberal Party on matters of federal-provincial relations.

The bill would change provisions of the Immigration and Refugee Protection Act to provide sanctuary in Canada for American and other countries' war resisters on moral, political or religious grounds.

[46] The campaign was heated at times, and on election night, harnessing the NDP's unprecedented levels of support, Nash defeated him to regain her old seat.

[49] At his campaign launch in London, Kennedy criticized the government's Bill 115 to ban teacher's strikes and freeze wages.

Early polls placed Kennedy ahead of other candidates to replace Premier McGuinty, helped by his name recognition from his federal and provincial work, and his role as director of the Food Bank.

[56] In a poll of Ontarion released on November 29, 2012 by Forum Research, 37% said they would support Kennedy, followed by Sandra Pupatello (23%), Kathleen Wynne (19%), Eric Hoskins (7%), Glen Murray (6%), and Charles Sousa (4%).