Incumbent Drew Dilkens holds the strongest position in the October 26 Windsor mayoral race, backed by his twelve years in office, recent pledges to maintain property tax increases at or below inflation, expand council oversight through a permanent finance committee, and pursue provincial responsibility for the E.C. Row Expressway. Main challenger Fred Francis, a longtime Ward 1 councillor, has positioned his campaign around affordability, ending strong mayor powers, and limiting debt, while raising questions over a June city hall security sweep referenced in a police letter noting the election year. The remaining nine candidates, including Aaron Day and Kat Pasquach, register minimal support amid a crowded field where only Dilkens and Francis have prior municipal experience. Trader consensus reflects the incumbent’s structural advantages six weeks before ballots close.