City of Ambition: Why New York’s Mayoral Contests Still Shape the American Century

Every fight for City Hall has prefigured the battles to come in Washington.

Tammany Hall, New York City’s powerful and infamous political machine, controlled it in the 1800s.

Fiorello LaGuardia, one of NYC’s greatest mayors, was elected in 1933.

From the 18th-century lodges of Tammany Hall to Zohran Mamdani’s street rallies, the battle for New York’s City Hall has always held up a mirror to America. The city’s mayoral elections have been a barometer of national change, where anxieties over class, race and power have played out in miniature before echoing across the republic.

Well before the glitter of glass towers and the grime of subway tunnels, the script for the struggle of mastery of NYC has been a familiar one: reformers versus bosses, immigrants versus elites, dreamers versus dealmakers.

Though he never held any public office, urban planner Robert Moses cast a long shadow over NYC.

Tammany Hall, founded in 1789 as a patriotic club, was reborn in the 19th century as America’s most famous political machine. For generations, its leaders - often Irish Catholic ward bosses - offered jobs, welfare and citizenship papers to new immigrants in exchange for loyalty at the ballot box.

Machine politics

Reformers such as Fiorello La Guardia, elected as New York City’s mayor in 1933, rose to dismantle Tammany’s grip and professionalise city government, only for power to pass to new kinds of machines. The most famous among these was the unelected bureaucratic empire of Robert Moses, immortalised in Robert Caro’s non-fiction masterpiece ‘The Power Broker’ (1974), and later, the corporate managerialism of Michael Bloomberg, who recast the mayoralty as the city’s chief executive.

Now, as Mamdani, the Ugandan-born, Queens-raised democratic socialist, ascends to City Hall, the mirror once again reflects a city wrestling with what it wishes to become.

That said, Mamdani’s victory over Andrew Cuomo was less about charisma than fatigue, almost a revolt against the transactional centrism and real-estate dominance that long defined New York politics.

The millennial progressive had made his Muslim faith a visible and unapologetic part of public life, something that would once have been politically unthinkable in post-9/11 New York.

The race for mayor of New York has always mattered because it has never been merely municipal. Governing this city is akin to governing a world within a republic – a world with a 100-billion-dollar economy, eight million tempers and countless contradictions.

In the late nineteenth century, Tammany Hall was a veritable red-brick cathedral of corruption that traded jobs for votes and loyalty for liquor. Its infamous bosses like John Kelly, Richard Croker and Charles Murphy governed through favours and fear. Immigrants arrived, swore allegiance and received contracts (or clemency) in return. It was government by the handshake, and for half a century, it worked until Fiorello La Guardia stormed in. A half-Italian, half-Jewish reformer with the righteous impatience of a street preacher, La Guardia, backed by Roosevelt’s ‘New Deal,’ broke Tammany’s grip and married municipal reform with federal muscle.

Then came Robert Moses, who never held any public office but who proved an unstoppable force of nature. Moses paved his own republic of concrete. He built bridges, tunnels, and parks, bulldozing neighbourhoods and mayors alike. The men elected to City Hall merely fought for relevance in his shadow.

Urban decay

By the 1970s, this empire of asphalt was cracking as the city’s finances collapsed, crime soared and despair set in. The 1977 blackout - an eerie, almost Biblical night when looters rampaged through Brooklyn and the Bronx while the skyline flickered dark - seemed to confirm New York’s descent. The city that never slept had turned into one that could no longer pay its bills.

When Ed Koch, a former congressman from Greenwich Village emerged from that darkness to win the mayoralty in 1977, he promised not hope but competence. “How’m I doing?” he would ask passersby, half self-deprecating, half self-assured. And for a time, New Yorkers, weary of their city’s decline, seem to approve.

But familiarity bred scandal. By Koch’s third term in the mid-1980s, corruption had seeped through City Hall as investigations into the Parking Violations Bureau uncovered a web of kickbacks, patronage and contracts-for-favours that sent several of Koch’s aides to prison. The mayor himself escaped formal blame but not moral culpability.

When David Dinkins succeeded him in 1989 to become the city’s first Black mayor, his victory seemed to herald a gentler New York. For a brief moment, the city exhaled. But the idyll soon ruptured with the Crown Heights riots of 1991, that sparked by a car accident and that killed an African-American child while heightening tensions between Black and Jewish residents. Dinkins’s measured instincts, once praised as humane, were now recast as ‘weakness.’

Two years later, Rudy Giuliani, a former federal prosecutor who had built his career locking up mobsters, rode into City Hall promising order. The mafia, long entwined with the city’s underbelly in construction, sanitation and even the police unions that quietly financed campaigns, began to crumble under federal indictments. Giuliani’s triumph lay in taming it.

Under Guiliani’s tenure, crime plummeted and property values soared. Wall Street once again strutted with swagger. And yet, civility declined. Policing became aggressive, even brutal.

This was followed by Michael Bloomberg’s technocratic reign, which was a three-term era of metrics and mayors as managers. He made the trains run and the parks bloom, but he also turned vast swathes of the city into playgrounds for global capital. By the time Bill de Blasio campaigned in 2013 on “a tale of two cities,” inequality had become New York’s defining condition. Eric Adams, who succeeded him in 2021, promised to be tough on crime, friendly to business and empathetic to workers. However, his administration soon floundered under federal probes and fiscal strain.

Now comes Mamdani, whose rise marks the pendulum’s swing back to ‘idealism,’ such as it is. Young, South Asian, socialist - Mamdani has certainly upended the city’s political grammar in the age of Trump and MAGA.

Every NYC mayoral race in every era has mirrored a deeper fear. In the 1930s it was corruption; in the 1970s bankruptcy; in the 1990s crime; in the 2000s terrorism and inequality; now it is the cost of living and the slow strangulation of the working poor.

The mayoral contest also exposes the city’s moral oscillation between order and freedom, wealth and fairness. Beneath the slogans lies the enduring question of who owns New York? The financiers who light up its skyline or the millions who clean, drive, cook and teach within it?

New York’s mayor wields more influence than many heads of state, shaping national policy on policing, housing, education and climate. Each election therefore becomes a referendum on the American city itself.

La Guardia’s liberal reformism prefigured Roosevelt’s New Deal. Lindsay’s patrician progressivism reflected the optimism and unrest of the 1960s. Giuliani’s law-and-order crusade foreshadowed post-9/11 conservatism. Bloomberg’s managerial modernism anticipated the technocratic centrism of the Obama era. Mamdani’s ascent will signal another turn in the days to come.

In his magisterial book, ‘The Power Broker’, Robert Caro observed that “power doesn’t always corrupt; it reveals.” So too with New York’s mayoral elections. They reveal the city’s moral pulse and its political restlessness, its unending appetite for reinvention. From the gaslit corridors of Tammany to the LED glare of Times Square, every race for City Hall has been a fight for the soul of modern urban life.

And in that bruising fight, New York remains what it has always been: the ultimate city of ambition.