The June 30 by-election in Trinity-Spadina pits the NDP's Joe Cressy against the Liberals' Adam Vaughan in the final race before the district gets split up next year. It's also the first contest in TrinSpa's 26-year history that hasn't seen Tony Ianno or Olivia Chow on the ballot.
The riding's story is one of overlapping, intersecting political dynasties, all vying to represent a high-profile chunk of downtown Toronto.
1987 Electoral boundary commission sets out new federal riding of Trinity-Spadina.
1988 The NDP's Dan Heap (twice previously elected member of Parliament for the riding of Spadina) beats Liberal challenger Tony Ianno to become the new district's first MP.
1991 Olivia Chow, a former school board trustee and assistant to Heap, is elected to Metro council, representing the ward called Downtown.
1993 Ianno becomes MP after beating NDPer Winnie Ng.
1994 Chow is re-elected to Metro council.
1997 Ianno successfully fends off a challenge from Chow, who runs for the NDP in the federal election. Five months later, Chow is elected to represent Ward 24 Downtown on the new amalgamated Toronto city council.
2000 Ianno beats NDP candidate Michael Valpy, a journalist for the Globe and Mail. Municipally, Chow is elected to the new Ward 20 Trinity-Spadina after council's seats are reduced from 56 to 44.
2003 Chow is re-elected.
2004 Ianno defeats Chow for the second time in a federal race.
2005 Chow resigns from city council ahead of her third federal run.
2006 Chow finally topples Ianno. But Chow's chosen successor for her council seat, former assistant Helen Kennedy, is bested by Citytv reporter Adam Vaughan, son of former councillor Colin Vaughan (1972-76).
2008 Chow keeps her seat, holding off the Liberals' Christine Innes, Ianno's wife.
2010 Adam Vaughan is easily re-elected. Mike Layton, son of Chow's husband, NDP leader Jack Layton, becomes councillor for neighbouring Ward 19 Trinity-Spadina.
2011 Chow again beats back Innes in a campaign chaired by Joe Cressy, son of former councillor Gordon Cressy (1978-82).
2014 Chow resigns from Parliament to run for mayor, triggering a by-election for her seat. Liberal leader Justin Trudeau, son of former prime minister Pierre Elliott Trudeau, bars Christine Innes from seeking the party's nomination. She says it's because she wouldn't agree to run where he wanted the next time; he says it's because she and Ianno bullied riding association members. Innes sues Trudeau for defamation. Trudeau recruits Vaughan, who walks away with the Liberal nomination and resigns from council. The NDP acclaims Chow's pick, Joe Cressy, as its candidate. Mike Layton, who served on council with Vaughan, endorses Cressy. Vaughan claims that his father, Colin, while working on Mitchell Sharp's 1968 bid for the Liberal leadership, played a part in bringing support to Pierre Trudeau once Sharp withdrew from the contest.