A longtime member of the Ontario New Democratic Party, he left the party because of the failure of NDP Premier Bob Rae's government (who is no relation to Kyle Rae) to pass long-promised reforms 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 supported Barbara Hall against David Miller in the 2003 mayoralty election. Because of his long running and historic criticism of the NDP's legislative failure on gay rights issues, Rae surprised many when he endorsed former Premier Rae when the latter 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."