New York has a tradition of larger-than-life mayors who've become characters to conjure with in the national political imagination. Governing a center of money, media, and social movements gives Gotham's chief executives a disproportionate role in defining the country's assumptions about big cities.

The modern era in New York politics is usually associated with such theatrical figures as the dapper songwriter and Broadway Boulevardier, "Gentleman" Jimmy Walker, who symbolized the Jazz Age of the 1920s until he was driven from office by a corruption scandal. Subsequent mayors included the five-foot-two-inch titan Fiorello La Guardia, "the little Franklin Roosevelt," a raging reformer who could campaign (and curse) in five languages. Later there was 1960s matinee idol John Lindsay who made liberal hearts go atwitter even as his local version of the Great Society sent the city onto greased skids. In the 1980s there was Ed Koch, a Borscht-belt comedian who rescued the city from bankruptcy while playing the role of mayor. And of course there's America's mayor, 9/11 hero Rudy Giuliani, who saved the city from crime by playing the role of a Republican playing a Democrat playing a Republican.

As a state senator in the 1920s, Jimmy Walker's approach to the city's tensions was to bring people together by legalizing Sunday baseball, boxing and movies. Walker, put in office by Tammany Hall, the city's legendary Irish Catholic political machine, would have liked to legalize Sunday drinking too, but in the Prohibition era it was outlawed for the entire week. As mayor, Walker rarely allowed his job to interfere with his social life. He paid his personal bills with contributions from people who did business with the city and he paid the city's bills by borrowing. By 1932, explains historian Martin Shefter, "one third of the entire city budget was devoted to debt service" and its total debt, conveniently financed by Wall Street just a few blocks from City Hall, "nearly equaled that of all the 48 states combined."

The city, which had to borrow from the banks to meet its payroll, had been reduced to a ward of financier J.P. Morgan. When Walker and his gorgeous mistress left for Europe, walking away from the bribery and shakedown scandals he'd help create, his temporary successor as mayor was John P. O'Brien, a loyal Tammany guy. Asked who his police commissioner would be, O'Brien famously replied, "I don't know, they haven't told me yet."

With the city suffering from a 25 percent unemployment rate, Fiorello La Guardia, who despised the bosses of both Tammany and big business, came in to clean up the mess. Elected in 1933 as a fusion candidate backed by both the Republicans and anti-Tammany reformers, he won with only 40 percent of the vote in a nasty three-way race by somewhat unfairly accusing an opponent of being an anti-Semite. "In exploiting racial and ethnic prejudice," wrote Robert Moses, "La Guardia could run circles around the bosses he despised and derided. When it came to raking ashes of Old World hates, warming ancient grudges, waving the bloody shirt, turning the ear to ancestral voices, he could easily out-demagogue the demagogues."

La Guardia, a tough campaigner who bragged, "I invented the low blow," carried the day with an unlikely coalition of Italian plebeians, WASP patricians and Jewish socialists, in the patronage-driven government he inherited, the surgeons hired for city hospitals by Tammany Hall had to be tipped if you expected them to operate.

La Guardia was revered by left-wing New Dealers. They saw him as moving New York toward European style social democracy, if not outright socialism. But La Guardia was more paternalist than socialist. Tammany Hall served as a just-off-the-boat employment agency for new arrivals. La Guardia saw himself as a benign padrone who would similarly look after a population just a half-generation removed from peasantry by providing the same services honestly and efficiently.

In 1935 he issued an emergency proclamation temporarily banning the sale of baby artichokes in the city's public markets. The target was the Harlem racketeers shaking down grocers "who purchased, under force, this delicacy especially valued by the Italian community." Accompanied by bugle-blowing police officers, La Guardia shouted out the proclamation from a flatbed truck outside a wholesale market in the Bronx. "I want it clearly understood," La Guardia said in his ringing falsetto, "that no bunch of racketeers, thugs, and punks is going to intimidate you as long as I am mayor of the city of New York."

In the early 1940s, while the U.S. and USSR were allies of convenience in the war against Hitler, a trade delegation from the Soviet Union dressed in its diplomatic finery came to visit La Guardia. La Guardia, the man of the people, looked at the Soviet diplomats and then at his own baggy paints and frayed shirt: "Gentleman," he said, "I represent the proletariat."

He was beloved, explained Supreme Court Justice Felix Frankfurter, because he "translated the complicated conduct of the City's vast government into warm significance for every man, woman and child." But by transferring patron/client relationships from the immigrant neighborhoods to City Hall, La Guardia turned New York into an administered city of clients rather than citizens.

In the short term, La Guardia screamed and bullied his way to better government. La Guardia, said New Dealer Rexford Tugwell, treated his own staff like "dogs." In one famed incident he called in a stenographer in order to humiliate a commissioner who was present. He shouted at her, "If you were any dumber, I'd make you a commissioner." La Guardia who rarely took a vacation, employed the technique of his hero, former New York City Police Commissioner Theodore Roosevelt, popping in to city offices unannounced to catch people goofing off. A mayor who gave a "prize" he called the "Order of the Shankbone" to the official who had made the biggest mistake since he last met with them was not to be trifled with. "It would be almost but not quite fair," wrote Tugwell, "to say that he was an instructive dictator."

La Guardia paid off the banks, promoted honest and efficient government by expanding civil service appointments and allied himself with Franklin Roosevelt, making New York into "the New Deal City." La Guardia, writes historian Thomas Kessner, became a master at milking money from the federal government. He was in Washington twice a week where he enjoyed extraordinary access to the president. Half joking, FDR said of La Guardia, "Our Mayor is probably the most appealing person I know. He comes to Washington and tells me a sad story. The tears run down my cheeks and the first thing I know, he has wangled another $50 million."

La Guardia made good use of the money. He hated lawyers, calling them the "semi-colon boys." He loved architects and engineers who, with the help of federal grants, built the East River (now FDR) Drive, the Triboro Bridge, the Lincoln Tunnel, and the Queens Midtown Tunnel during his tenure as mayor. But not even the vast flow of federal money could keep up with the city's spending. La Guardia added an array of new taxes and his comptroller, who dismissed deficits as "entirely a bookkeeping transaction," adopted the old Tammany policy of rolling one year's expenses over into the next year's budget."

The mayor didn't help matters with his relentless hostility to business. He pledged to make New York a "100 per cent union city," and when businesses threatened to leave, he threatened to blacklist them. "The forces of organized money," he argued, "are unanimous in their hate for me." When a 1944 report spoke of "the alarming flight of industry to younger cities," creating "ghost neighborhoods," he responded with plans for even more public works. Without massive city spending to absorb the returning veterans, he feared that, as in the worst days of 1930s, labor violence "hell will break loose."

The glory years were indelible but brief. By the late 1930s, not even La Guardia's special relationship with FDR could keep the city on an even keel fiscally. When he came into office La Guardia used federal money to pay off the city's debts to J.P. Morgan and other banks. By the end of his three terms, the city was once again in hock to the bankers. New York, explained the Citizens Budget Commission, "faces a crisis in its fiscal affairs" because spending independent of relief was growing three times faster and debt five and a half times faster than the population. The mayor's ally, Comptroller Joseph McGoldrick, adopted the Tammany practice that La Guardia had once denounced of financing current expenditures with debt imposed on future generations. World War II temporarily rescued the city from its fiscal fate and the return of machine politics in the 1950s temporarily slowed the rate of increase of city spending, but except for boom times New York would never again be able to afford its government.

La Guardia kept the budget in tenuous balance in part through substantial tax hikes. Levies such as the rent occupancy tax and the sales tax passed as 1930s emergency measures became permanent. The mayor added a utilities tax and raised the property tax to record levels. "High taxes and declining terminals and docks," writes Kessner, "were helping to drive the garment and printing industries out of the city." But when the New York Board of Trade told the mayor about the exodus be attacked them as "cowardly and despicable" for spreading "cheap propaganda" and a "deliberate lie."

While Tammany's patronage hires could be fired, the vast civil service La Guardia created was expensive, untouchable and, after La Guardia left office, unaccountable. Every subsequent mayor would have to figure out how to work his way around them. Surveying the city's finances in 1944, Tugwell warned presciently that La Guardia's policies in buying off class strife had "made municipal bankruptcy inevitable."

The passing glory of the Fiorello and Franklin friendship fueled an illusion that lives to this very day. Rudolph Giuliani notwithstanding, La Guardia remains in both persona and policy the standard against which all mayors are judged. The Tammany profligacy preceding La Guardia forced the city to beg the bankers for aid. The machine's excesses could be, as La Guardia showed, quickly cut by efficient administration. But while the Tammany hacks he displaced could be fired, the civil servants he put in their place were headless nails. Protected by civil service rules, they were insulated from the consequences of their own actions, let alone the actions of a future mayor trying to call them to account. "The Little Flower" left the city with uncontrollable costs. His heirs would end up begging both the bankers and the federal government for aid even as they taxed their own constituents to the hilt in order to support La Guardia's "reforms."

By the war's end, Tammany, despite the protests of some Catholics like former presidential candidate Al Smith, who had grown increasingly conservative, embraced the New Deal wholeheartedly. It regained City Hall by choosing the charming World War II veteran William O'Dwyer as its candidate. The eleventh consecutive Irishman to receive Tammany's nod for mayor, O'Dwyer led the city through a wave of post-war strikes at a time when both leftwing politics and mob influence were at their peak. Like the New Dealers who were both loyal Americans and sympathetic to the Soviet Union, O'Dwyer was a good leftist supporter of civil rights and deeply entangled with the mob. And often there was little contradiction between the two.

In his classic essay "Crime as an American Way of Life," Daniel Bell notes that one reason that urban machines could take left-wing stances is that they sometimes allowed the mob to finance their campaigns rather than becoming beholden to "moneyed interests." Both the mobs and the unions took advantage of New York's geography. A fast-moving but congested city built on an island of narrow streets and tall buildings, each of Gotham's innumerable bottlenecks presented an opportunity for the unions to apply economic pressure and for the mob to engage in shakedowns. At the time it seemed not to matter all that much. New York with one million people employed in industry was the greatest manufacturing city in the world. The city barely shrugged when O'Dwyer's connections with Albert Anastasia of Murder Inc. forced him from office in 1951. Like Walker, O'Dwyer went off into political exile with a beautiful young actress on his arm.

Unfazed by O'Dwyer's disgrace, the city accepted mob-tainted Tammany's Robert Wagner, Jr., the cautious son of the New Deal senator famed for his pro-labor legislation. Wagner, who went on to serve three terms from 1953 to 1965, was as upright as O'Dwyer was crooked, but their New Deal liberalism was largely indistinguishable. Both men built hundreds of new schools, playgrounds, public housing projects and hospitals. The 1950s were the heyday of working-class politics. The achievements were impressive. New York pioneered the development of co-operative housing, group health coverage, and pre-paid medical plans. But the city also took the lead in policies that would prove problematic.

In most of the U.S. rent-control laws were a temporary response to World War II. In New York rent control became permanent and consequently so did the city's housing shortages. Tenant politics in New York, the big city with the lowest homeownership rate, became the new class struggle, in Gotham, candidates accused their opponents of being soft on landlords or weak on rent control with the same fervor and intelligence that accompanied accusations of Communism elsewhere.

La Guardia had tried to draw a sharp distinction between public- and private-sector workers, explaining that "I do not want any of the pinochle club atmosphere to take hold among city workers." But it was an untenable distinction. In 1958 Wagner brought labor struggles into the halls of city government when he signed what was known as "the little Wagner act," which made New York the first city to give its municipal workers the right to unionize. The rise of public-sector workers as a political force entailed the decline of parties. City workers had been Tammany's key constituency; after Wagner they would become a powerful force in their own right. But where Tammany was always forced to consider a wide range of interests, public-sector unions were relentless advocates for their own narrow advantage.

Between a unionized work force, rapidly expanding social services and the need for public works projects, the city was forced repeatedly to raise taxes and borrow. Wagner claimed that he had no choice since "human needs are greater than budgetary needs." It was a logic that would come back to haunt New York during the days of John Lindsay's mayoralty.

Lindsay, a handsome man who cut a dashing political figure, was celebrated by the national press as the second coming of JFK. He ran for mayor in 1965 not only as a Republican but also, like La Guardia, as the fusion candidate of G.O.P. mavericks, the Democratic Party's upper-middle-class reform clubs, and the left-liberals of New York City's Liberal Party. In a Kennedyesque campaign, he promised to get the city moving again after the supposed stagnation of the Wagner mayoralty. In fact the city was in the midst of an economic boom.

The 1965 mayoral race was a three-way contest between Lindsay, Abe Beame, the Brooklyn candidate of the Democratic regulars who was almost as liberal as Lindsay but as short and drab as Lindsay was glamorous, and the conservative William F. Buckley, Jr.. Much of what Buckley campaigned on, such as workfare for welfare recipients and enterprise zones for poor neighborhoods, is now mainstream. But Lindsay and Beame took advantage of Buckley's rhetorical excesses and opposition to the 1964 civil rights act to paint him as a dangerous fascist who planned to set up concentration camps in New York. Asked what he would do if elected, Buckley quipped, "Demand a recount." He didn't need to; Lindsay won with 43 percent of the vote.

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