1996 Ontario Liberal Party leadership election

The contest featured seven official candidates: MPPs Anna-Marie Castrilli, Joseph Cordiano, Dwight Duncan, John Gerretsen, Gerrard Kennedy, and Dalton McGuinty, and businessman Greg Kells.

She defeated frontrunner Murray Elston by nine votes on the fifth ballot, becoming the first woman to lead a major party in Ontario.

[2] The party under McLeod had been leading in the polls for most of the period from 1992 to 1995, and were generally favoured to benefit from the swing in support away from the NDP.

However, the party hurt its credibility through a series of high-profile policy reversals in the period leading up to the election, the most notable being her stance on rights for same-sex couples.

[3] Former cabinet ministers Sean Conway, Murray Elston and Gerry Phillips were initially the leading contenders for the leadership.

At a preliminary planning meeting hosted by the party in January 1996, prospective candidates sent representatives, including the four of the six MPPs eventually entered the race (excluding Duncan who was supporting Conway at the time, and Kennedy who was not an MPP at the time); MPPs Conway, Phillips, Dominic Agostino, Richard Patten; federal environment minister Sergio Marchi, Toronto lawyer John Campion; and Robert McMurtry, brother of former Progressive Conservative Attorney General Roy McMurtry.

[4] Conway publicly declared his intention to run in the summer of 1995,[5][6] and was widely perceived to have accumulated enough support within the caucus and the wider party to secure victory, but announced in late January 1996 that he would not be a candidate.

[7] Phillips announced his bid in late March after Conway's exit, quickly emerging as the frontrunner and garnering support from half of the caucus, but withdraw in April due to a heart ailment.

[8] Duncan became the first caucus member to formally announce a bid in June, followed shortly by Kennedy in mid July.

Confidence with his chances, his campaign allowed a CPAC camera crew to shadow him throughout the convention, capturing a number of less-than-flattering moments for Duncan.

Gerrard Kennedy, 36, only entered the legislature at the end of May, when he won the by-election to replace former Premier Bob Rae in York South.

Unlike Duncan, Cordiano delivered 80% of his delegate, and was thereby largely responsible for McGuinty's victory over Kennedy for the party's leadership.

In a highly divisive and race-driven contest, Castrilli was defeated for the party's nomination in York Centre by Monte Kwinter.

Castrilli's indecision after the first ballot caused the party to institute rules imposing time limit and irrevocable written notice requirement for withdrawal in future conventions.

McGuinty lost the 1999 election, but successful fought back a leadership review later in 1999 with 80% support and remained leader.

Kennedy left the government and unsuccessfully sought the federal party leadership in 2006, but was instrumental sealing the victory for Stephane Dion, another victor who started from fourth place.

Kennedy again contested the province party leadership in 2013, coming in third and throwing his support to the eventual winner Kathleen Wynne over frontrunner Sandra Pupatello (who served as Duncan's campaign chair in 1996).