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Outside of his political career, Lastman ran a discount furniture store, Bad Boy Furniture. It eventually went bankrupt, but was later resurrected by his son.

Re-elected in November 2000 with an 80% majority, his closest opponent, civic activist Tooker Gomberg, drew just a little more than 8% of the vote.

Lastman shared 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 ChrétienJoseph Jacques Jean Chretien (born January 11, 1934, Shawinigan, Quebec) was the twentieth Prime Minister of Canada, serving from November 4, 1993, to December 12, 2003. The Rt Hon. Jean Chretien Rank 20th Term of Office November 3, 1993 December 12, 2003 to end homelessnessHomelessness is a situation in which a person does not have a permanent place of residence. This is distinguished from nomadic cultures where that condition is considered normal. There are a number of causes of homelessness. In areas with high unemploymen in Toronto, and appointing Jane JacobsJane Butzner Jacobs (born 1916) is a writer, activist, and city aficionado. She was born in Scranton, Pennsylvania and now lives in Toronto, Ontario. In 1944 she was married to Robert Hyde Jacobs. She has two sons, James Kedzie, born 1948, and Edward Deck, the ethicist and urbanist to head the Toronto Charter Committee to explore the potential for more autonomy for TorontoA Province of Toronto is the goal of many urban politicians and citizens' groups in Toronto, Ontario, who run candidates for office to promote the idea of separating Toronto's 2. 4 million residents politically from Ontario and the suburban 'Greater Toron. Jacobs had publicly endorsed Gomberg.

Lastman was supported by many in North York for operating that city efficiently and effectively, and for keeping property taxes low. He was also criticized for not listening to other city councillors. As mayor of Toronto, he was criticized for not being able to control city council, and for being too close to lobbyists.

Lastman was an outspoken politician, a trait that was sometimes problematic, but that also endeared him to many Toronto residents. He was sometimes prone to committing public gaffes. For example, Lastman injured Toronto's bid for the 2008 Olympic GamesOlympic Flame from Olympia to the opening ceremony. The Olympic Games or Olympics are an international multi-sport event taking place every fourth year. Originally held in ancient Greece, they were revived by a French nobleman, Pierre Fredy, Baron de Coub when he was asked whether he would go to a meeting in MombasaMombasa is a major port and is the second largest city in Kenya. The port serves both Kenya and countries of the interior using the Uganda Railway. The city has a population of around 900,000 and is located on Mombasa Island. The town is mainly occupied b, KenyaKenya (pronounced KEN-ya; the pronunciation KEEN-ya is archaic) is a country of eastern Africa, bordering Ethiopia, Somalia, Sudan, Tanzania, Uganda and the Indian Ocean. Nairobi is its capital and largest city. Republic of Kenya ( In Detail) (Full size), and expressed concern about ending up in a pot of boiling water. While Lastman apologized profusely for the joke, it brought into question Toronto's reputation as an international city. Lastman was also ridiculed for greeting and shaking hands with members of the Hells AngelsThe Hells Angels (without the apostrophe), formed in 1948 in Fontana, California (where the local chapter remains active), epitomized the outlaw biker counterculture of the 1960s, and have been associated with gang rape, white supremacy, and murder. The F motorcycle gang when they held a convention in Toronto. He was further hurt by the announcement that he had an extramarital affair which resulted in illegitimate children.

On November 10, 2003, David Miller was elected to replace him as city mayor. Lastman retired from politics, due to his deteriorating health. He had a heart attack on September 9, 2004, but is reportedly "doing absolutely fantastic", according to his son, Blayne.