After his retirement from the police force, Stewart entered municipal politics, being elected mayor of the Town of Summerside in 1985. He was re-elected in 1988 and 1991. In 1994, he became the first mayor of the now City of Summerside (Summerside formerly being a town). He was re-elected in the municipal elections held in 1997, 2000, 2003, 2006 and 2010. In
1993, Stewart ran in a federal election as the
Progressive Conservative candidate for the
riding of Egmont. He was defeated by then-incumbent
Liberal MP Joe McGuire, who won with a plurality of approximately 3,700 votes. He was accused of wasting $1.3 million of taxpayers' money, which was forwarded as a purported deposit towards a Michael Jackson tribute concert that never ended up happening, "In January 2011, the city filed a complaint with the United States District Court, Northern District of California, San Jose Division, for fraud, conspiracy to commit fraud, negligent misrepresentation and rescission (rescinding) of a contract against Katrina Berg Sussmeier and Starlink Productions Inc." At the
2014 Summerside mayoral election, Bill Martin, a Summerside businessman, was elected mayor with a vote of 4614 compared to Stewart's 2092, thus ending Stewart's 29-year run as mayor of Summerside. ==Goals and objectives==