[2] He won the mayoral election,[7] although his victory was subject to a judicial recount due to his margin of just 30 votes over second-place finisher Greg Durocher.
[10] In 2001, he supported the expansion of GO Transit service in Cambridge as an alternative to a controversial new highway construction proposal that would have disrupted the city's Cruickston Park.
[11] Early in his term he scored a significant achievement for the city, successfully lobbying the University of Waterloo to establish its new School of Architecture campus in a vacant factory building in Cambridge.
[12] Around this time, Brewer and Fred Kent, the city's regional councillors, were facing some scrutiny for often voting differently at the Waterloo Region council level from the wishes of Cambridge's city council, but Craig earned himself a reputation as a "diplomat" for refusing to participate in the criticism of Brewer and Kent; instead, he took personal responsibility for a lack of communication between the city and regional councillors, caused by the provincial government's recent separation of the two roles.
[17] In his third term in office he advocated for Cambridge to be included in Waterloo Region's rapid transit plan, which had initially included only Kitchener and Waterloo,[18] and supported a plan to replace many traffic lights on the city's Franklin Boulevard with roundabouts.