Mel Lastman became wealthy and well known by owning a discount furniture store (called "Bad Boy," which had television and radio advertisements with the slogan "Who's better than Bad Boy? Nooooooooooooobody!"). Although the company became the largest furniture retailer to ever go bankrupt in Canadian history, he was elected as mayor of the former Borough of North York in 1972 and successfully kept that position for 25 years. Lastman became the first mayor of the amalgamated City of Toronto on January 2, 1998, defeating former (original City of) Toronto Mayor Barbara Hall. He is claimed to be the longest serving mayor of any major urban area in North America.
He was re-elected in November 2000 with an 80% majority. His closest opponent, civic activist Tooker Gomberg, drew just over 8% of the vote. However, Lastman adopted Gomberg's three main campaign planks: committing Toronto to 100% recycling diversion by 2010 to replace the controversial Adams Mine Dump plan, agreeing with Prime Minister Jean Chrétien to end Toronto's homelessness crisis with a C$700M injection of funds (which were never delivered), and appointing, as his very first act of office on re-election, Jane Jacobs, the ethicist and urbanist and probably Toronto's most celebrated activist, to head the Toronto Charter Committee to explore the potential for more autonomy for Toronto. Jacobs had publicly endorsed Gomberg.
After his re-election, Lastman faced a number of challenges including: