Background
Before attending the University of Victoria, Fleming spent two years (1993–95) at Camosun College which later awarded him the 2008 Distinguished Alumni Award. where he was elected the president of the UVic Students' Society. He was active in acquiring a universal access to BC Transit for students through a U-Pass system. Fleming graduated with a bachelor of arts with a major in history. Following graduation, he started work with a communication consulting business. He stood as a candidate for Victoria City Council in the 1999 municipal elections as a member of the Victoria Civic Electors which ran a joint slate of seven candidates with the Green Party. Fleming finished third in voting, securing him a seat on the eight-member council. Fleming was re-elected to the council in 2002 election. He traveled to El Salvador, in 2004, as part of a 13-member delegation of election observers to monitor the presidential election.
While on Victoria City Council, Fleming gained a reputation for being a "fiscally prudent democratic socialist". He supported the legalization of secondary suites, the construction of the Save-On-Foods Memorial Centre (but voted against the option to have it privately operated), and amendments to bylaws to target aggressive panhandling. As a Director on the board of the Capital Regional District, Fleming was vice-chair of the CRD Housing Corporation where he advocated for an Affordable Housing Trust Fund. He sat on the Victoria Regional Transit Commission and has advocated for transit service expansion and light rail in the Capital Region. He was a member of the Provincial Capital Commission and was the only member to vote against, due to concerns with the long-term lease agreement and risks involved, replacing the plant and animal conservatory Crystal Gardens with the multi-media tourist attraction, The B.C. Experience, which filed for bankruptcy protection three months after opening.
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