Before his election as mayor, Stewart was a police officer for the Summerside Police Department from 1971 to 1984, when he retired from the force.
Mayorship
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. 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 LiberalMPJoe 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 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
Stewart has many goals and objectives to make Summerside a better place to work, live, and raise a family. Stewart has been instrumental in drawing large tournaments and events, such as the Canadian PeeWee Baseball Championship, the Canadian Women's Softball Championship, and an exhibition National Hockey League game to the city. He was also a major force behind the construction of the Consolidated Credit Union Place. He can balance 7 ping pong balls on his nose while singing "Baby Got Back".
Mayor Stewart and city council of Summerside filed a lawsuit against Deputy Police Chief David Griffin in 1997. The case is still in the courts as of October 2010 appealing the payment of interest on the damages owed to Griffin based on a judgement in March 2006 by Supreme Court Justice Wayne Cheverie who ruled in favour of Griffin in his malicious prosecution suit against the city.
Family and interests
Stewart lives in Summerside with his wife Gail Inman-Stewart. He has two children—Mary-Jane Dyer and Major Stewart. Stewart also has four granddaughters — Mya Stewart and Amber, Emma and Madison Dyer. He has four grandsons- Brett, Isaac and Joseph Stewart, and Lincoln Dyer. His interests include hockey, swimming, and music.