Rae graduated with a Honours Bachelor of Arts degree in History from Brock University in St. Catharines, Ontario. He also has a Master's Degree in History from the University of Birmingham, and a Master of Library Science Degree from the University of Toronto. Before he became involved in politics, Rae was executive director of the 519 Church Street Community Centre in the heart of the Church and Wellesley area.
He was first elected to Toronto city council in 1991 as a left-leaning councillor filling the seat vacated by Jack Layton (who was running for mayor at the time). He campaigned as an openly gay candidate and beat his closest rival by 1003 votes. He became the city's first gay councillor. During his first term, as Chair of the City's Personnel Committee he attempted, with Mayor June Rowlands support, to introduce affirmative action in the city's fire department. The motion was defeated.
A longtime member of the Ontario New Democratic Party, he left the party because of differences of opinion on gay rights issues. Rae led a local boycott of the NDP in the 1993 by-election in the riding of St. George—St. David (now Toronto Centre—Rosedale) to highlight his position. In recent years, Rae supported John Sewell's independent candidacy in the 1999 provincial election and federal Liberal Bill Graham. He endorsed former New Democratic Party Premier Bob Rae who successfully contested the Toronto Centre federal by-election on March 17, 2008 as the Liberal Party candidate. Kyle said of Bob, "He has a unique set of skills and experience, and I hope he wins .... His candidacy has my full support."
In 2002, he was sued for defamation by members of the Toronto Police Force after he sharply criticized a 2000 raid on "Pussy Palace", a lesbian bathhouse night. His calling the police "rogue cops" and "goons" and the operation a "panty raid" was criticized, and the officers alleged what was only a standard liquor inspection hurt their careers and reputations. A jury eventually decided that the seven officers were defamed and ordered Rae to pay $170,000. The settlement money was paid by the city from a fund that protects councillors from having to pay lawsuits from personal funds.
In May 2007, Rae renewed his call for a bylaw to further protect historic buildings. The proposed bylaw would give the City of Toronto the power to charge building owners who let historic buildings fall into disrepair. It would also give the city the power perform emergency repairs in certain cases, applying the bill to the owner's taxes. Rae's call came after the Walnut Hall, a historic Georgian Rowhouse, collapsed after decades of neglect. The building's various owners sought to tear it down and were prevented because of its historical value.
There has been some debate as to whether Rae represents the gay community. Writer Brent Ledger, who has interviewed Rae on several occasions, has written that Rae has been a disappointment for those who believed that a gay councillor would make a difference.
- ↑ City of Toronto councillor, Ward 27 profile, 
- ↑ Timothy Appleby, "Political Fallout Slight", Globe and Mail, p. A6, 13 November 1991.
- ↑ Donald Grant, "Proposal on Firefighters Rejected", Globe and Mail, p. A16, 2 February 1993.
- ↑ Scott Steel, “Rebuking the NDP”, Maclean's, 12 April 1993.
- ↑ Andrew Cash, "Citizen Sewell stands alone", Now Magazine, 20 May 1999, 
- ↑ Eleanor Brown, "Graham in the Balance", Eye Weekly, 24 June 2004, 
- ↑ Unnati Gandhi, Rae the councillor backs Rae the MP candidate, Globe and Mail, p. A9, March 6, 2008.
- ↑ Emily Sharpe, "Don’t cross the cops", Xtra!, 27 June 2002, 
- ↑ "Canada OKs Marriages", CBC News. 20 June 2003, 
- ↑ "The fight against 'demolition by decay,'" HeritageHome.ca, 
- ↑ "The Martyrdom of Walnut Hall," HeritageHome.ca, 
- ↑ Brent Ledger. Why is an answer too much to ask? Toronto Star. May 24 2008. pg. L4.