In the fascinating world of big city politics, there have always been interesting mayors. Fiorello LaGuardia in New York identified as a Republican but usually received support from opposition parties. He cozied up to Franklin Roosevelt in the 1930s, and in a historical poll taken in the 1990s, most observers ranked him as the greatest mayor in American history. Richard Daley of Chicago ran such a powerful machine in the Windy City that many believe he swung the 1960 election in Cook County to JFK, assuring the Democratic nominee of his victory in the presidential election.
There have been other colourful mayors remembered for good or ill. Taking the first-worst prize among scoundrel mayors is Chicago’s William H. “Big Bill” Thompson (1915–1923, 1927–1931), one of the most colourful mayors in the city’s history, if not the most corrupt. Big Bill, also known as “Kaiser Bill,” for his pro-German stand during World War I, accepted campaign funds from gangsters, including Al Capone. The leadership of New York City has seen a range of effectiveness from mayors like Jimmy Walker and John Lindsay to Ed Koch, Rudy Giuliani, and Eric Adams. And Buffalo, New York, once produced the only mayor to win the presidency, Grover Cleveland. Excluding Canada from this overview would be a mistake.
Several Canadian mayors stand out for their interesting or impactful tenures. Barbara Hanley (Webbwood, Ontario), the first woman elected as a mayor in a general election, and Hazel McCallion, known as “Hurricane Hazel,” for her long and forceful leadership in Mississauga, are prominent figures. Besides, Rob Ford’s controversial tenure and Naheed Nenshi’s progressive leadership both had lasting effects on Toronto and Calgary, respectively. Some might nominate Niagara Falls’s own Jim Diodati, often referred to as “Hollywood Jim,” for his relentless efforts to increase the Honeymoon City’s profile and bring big audience venues to town. Regardless, the upcoming mayoral elections in New York City and Toronto will soon challenge the patience, wisdom, and resilience of their residents.
In the Big Apple, the Democratic Party recently held a primary to select who would represent the party in this fall’s election. The sitting mayor, Eric Adams, chose not to run in the Democratic primary. Andrew Cuomo, the ex-governor who stepped down amid scandal, seemed poised to win before the election. Also on the ballot was Zohran Mamdani, a self-proclaimed Muslim socialist who has been sharply critical of the government of Israel and has promised to enforce the International Criminal Court’s arrest warrants for Benjamin Netanyahu if he visits New York. To the surprise of many, Mamdani toppled the political giant, defeating Cuomo in the June 24 election to become the first Muslim nominee of a major party in New York’s mayoral history.
Mamdani has also pledged to lower costs for the city’s impoverished and low-income residents by eliminating bus fares, providing public childcare, establishing city-owned non-profit grocery stores, creating rent-free zones, expanding affordable housing, and implementing a $30 minimum wage by 2030. He stands a splendid chance to win in November, but who is paying for this? His platform includes defunding the police in favour of social workers, who he believes can resolve conflicts peacefully and build lasting reconciliation. Stay tuned to find out if this works electorally in the financial capital of the Western World. As Nicolas Cage’s character Jack Campbell observes in Family Man, a 2000 movie also starring Tea Leoni, “No, this is the center of the universe. If I were living in Roman times, I would live in Rome, where else? Today, America is the Roman Empire and New York is Rome itself. John Lennon.” If Mamdani pulls this off, he will have turned the political world upside down and taken on what many call the second hardest job in American politics (after the presidency).
As for Toronto, in the 2022 municipal elections, city voters returned their incumbent mayor, John Tory, to office with a significant show of support (62 per cent of the vote). Tory, first elected in 2014, won his third term, to no one’s surprise. He had led the city sensibly and represented its interests in all ways with moderation and competency, if not flair. In 2023, however, it became public that Tory had been involved in a relationship with a member of his staff. Tory resigned, and a special election held in June 2023 resulted in Olivia Chow’s ascendancy to the mayor’s office.
Tory’s potential 2026 return is being discussed; although initially reluctant following his resignation, he’s expressed a renewed interest in his previous role. Considering the odd manner in which Chow has led the city (ignoring gang-style crime, telling people not to shop at Home Depot because it chose not to sponsor Toronto’s Pride Parade, allowing encampments of homeless people all over the city), the possibility of a scandal-stained candidate like Tory may not be as far-fetched as it sounds. Chow not only dissed Home Depot, but she also told people to shop at Rona because it was Canadian owned. Unfortunately, Chow was misinformed. Beyond that Home Depot is a top purchaser of Canadian lumber, meaning thousands of jobs are affected when she speaks off the cuff and has no command of the facts. Compounding the problem, Home Depot requires a new Canadian headquarters; when a mayor acts against a business as Chow did, how does that aid the city in creating jobs?
New York and Toronto represent the financial interests of their nations. A city’s economic activity, street safety, and quality of life hinge on who is mayor. In the next six to 18 months, these and other cities will be choosing their next leader. New York’s upcoming elections, and the citizens’ choices therein, may sway national politics, especially given the 2026 state and congressional elections. It will be worth keeping an eye on these developing stories. They might reflect our times as much as they reflect the cities themselves.
Dave Redekop is a retired elementary resource teacher who worked part-time at the St. Catharines Courthouse as a Registrar until being appointed Executive Director at Redeemer Bible Church in October 2023. He has worked on political campaigns since high school and attended university in South Carolina for five years, earning a Master’s in American History with a specialization in Civil Rights. Dave loves reading biographies.
