Around midnight on November 4, 1928, a nattily dressed man sidled up to Jimmy Walker’s table at Joe Pani’s Woodmansten Inn, on Williamsbridge Road in the Bronx, and whispered a message in the mayor’s ear. Walker cradled his paramour, the actress Betty Compton, and hurriedly exited the roadhouse, stopping only to apologize privately for his abrupt departure to the bandleader Vincent Lopez. “Arnold Rothstein has just been shot, Vincent,” the mayor said. “That means trouble from here on.”

Exactly one year later, James J. Walker was re-elected as New York City’s 97th chief executive by a wider margin than any of his six predecessors were and by a bigger plurality than any of his successors would receive for 50 years. In a city where mayors, such as the incumbent, Eric Adams, are barely tolerated, Jimmy Walker was idolized.

Walker and his second wife, actress Betty Compton, aboard the S.S. Manhattan in 1935.

A song-and-dance man at heart, he had written the lyrics to “Will You Love Me in December as You Did in May?” and as of December 1929, even after the stock market had crashed and Walker was poised to begin a second term with the trouble he had predicted reverberating daily, his adoring public would answer the song’s title query with a resounding yes.

The indictment last month of New York’s Eric Adams, the city’s 110th mayor, on public-corruption charges has conjured up the scandalous Roaring 20s that Walker embodied. But in 2024, with both an overwhelming migrant influx and the after-effects of a pandemic under a mayor who, like his predecessor, Bill de Blasio, lacks the muscle and vision of their predecessors, Mike Bloomberg and Rudy Giuliani, New Yorkers are doing more deploring than roaring.

Adams, a fellow bon vivant (but who, unlike Walker, invokes God as his chaperone), lacks the reservoir of goodwill that could easily have gotten Walker re-elected after he was finally forced to resign, in 1932, in the middle of his second term.

“Arnold Rothstein has just been shot, Vincent,” the mayor said. “That means trouble from here on.”

Mayor La Guardia exuded empathy. Lindsay defined charisma. Koch’s candor could elicit a guffaw. But New York loved Walker, a charming hellion, a witty, self-effacing, glib humanist, far more flawed, too, and compassionate than pictured previously, a man elevated and condemned by his own character, created and ultimately consumed by his times. He conjures up the anti-Trump—a dodgy philanderer who governed by making people feel good rather than angry.

“The crowd was in the Long Island Bowl for the second Sharkey-Stribling fight and the preliminaries were stumbling to a close and there came the rising whine of sirens from outside,” Red Smith remembered. “A stir and a babble ran through the crowd and heads turned away from the ring and it seemed everyone was standing and craning. Down an aisle swept Jimmy with his retinue, with a hand uplifted in jaunty response to the shouts that greeted him. And that entrance was more exciting than any of the 15 rounds of brawling that followed.”

One night, he arrived at a fundraising dinner for a Jewish organization after the last guest had finished dessert. Nobody was angry. He strode into the ballroom wearing a yarmulke, and when one woman shouted, “Jimmy, circumcision next?,” the mayor replied, “Madam, I prefer to wear it off.”

Then New York governor Franklin D. Roosevelt and Walker, 1928.

Contrary to conventional wisdom, Walker’s first term was, by many measures, a success. Thanks to the grooming of Tammany’s honest grafter, Charles F. Murphy, Walker had been elected mayor in 1925 after compiling an impressive record in the state legislature, joining Al Smith and Robert F. Wagner (as, you should forgive the expression, one of the Young Turks)—outlawing the Ku Klux Klan, licensing Sunday boxing and baseball, opposing censorship (declaring cunningly, “I have never heard of a girl being ruined by a book”), and leery of intrusions on personal liberties offered in the guise of protecting civic virtue (famously defining a reformer as “a guy who rides through the sewer in a glass-bottom boat”).

As mayor, he consolidated the hospital system, expanded the parks and bus service (benefiting a few friends who happened to own bus companies), began the demolition of the New York Central’s “Death Avenue” street-level railroad tracks on Manhattan’s West Side, and, with the help of the United States Supreme Court, froze the subway fare at a nickel. By the end of Walker’s first term, The New Yorker had concluded that, apart from his “freedom from any trace of meanness or bunk,” the mayor could “point to a fairly impressive list of achievements.”

Instead, Fortune’s Wheel would spin uncontrollably, its centrifugal force hurling the mayor himself into trouble of his own making. He was the guest of honor at a party conspicuously attended by a mobster known as the “Artichoke King” and organized on behalf of a Bronx judge who, it had just been revealed, had borrowed $19,500 from Arnold Rothstein, the notorious gambler.

When one woman shouted, “Jimmy, circumcision next?,” the mayor replied, “Madam, I prefer to wear it off.”

On the last day of his first term, Walker signed legislation that granted raises to the highest-ranking municipal worthies. When his own 40 percent pay hike—to $40,000, which he would donate to charity—was challenged, Walker was ready with a rejoinder that rang true to his constituents: “Imagine what they’d have to pay me if I worked full-time!”

If his work ethic seemed wanting, critics were unwise to underestimate Walker’s mental agility. His Torquemada, Samuel Seabury, the waspish legislative counsel who hounded him from office, was so convinced of Walker’s hypnotic gaze that he warned his assistants who were interrogating the mayor never to look him in the eye.

Walker never offered satisfying explanations for why he accepted what he described as “beneficences”—including the proceeds of a joint Wall Street investment account opened by a friendly publisher (whose son had wondered how the mayor could survive on his paltry salary) and that earned him $246,692.72, which he stuffed into a safe in his Manhattan apartment. Seabury uncovered several dodgy quids but no verifiable quos. As one newspaper editorial put it, “Judge Seabury did not prove Walker took crooked money. He did prove Walker took easy money.”

Still, Seabury recommended to Governor Franklin Roosevelt that the mayor be removed. Roosevelt, running for president, couldn’t afford the scandal. F.D.R.’s predecessor, Al Smith, conveyed the ultimatum to Walker, who would later write his former benefactor in an unmailed letter: “It did not take many years for you to repay me in the coin of Brutus.”

Thousands of well-wishers besieged the courthouse where Walker was testifying. When one asked if Walker could wangle an extra ticket to the proceedings, the mayor replied cheerfully, “You can have mine.” “Everyone is for you, Jim,” a supportive reporter told the former mayor. “All the world loves a lover.” “You are mistaken,” Walker corrected him. “What the world loves is a winner.” So, what does that make Eric Adams?

Walker leaves for lunch after a court hearing in 1932.

Like Eric Adams, whose grasp and greed never seems to have gotten beyond the provincial reach of the anachronistic office of borough president, Walker had no one to blame but himself for what was, at the least, his naïveté (a characteristic that, according to the scheming detailed in the federal indictment, was one thing that Adams seems innocent of). “No one can buy or sell me, but friends sometimes have made a fool of me,” Walker said.

Walker wanted to retire after one term, but hubris and the quest for vindication blinded him. In the fishbowl of City Hall, the scandals and the Depression stripped the dapper emperor of his new clothes. “If I had to sum up my feelings as mayor of the world’s largest city, I should say, ‘It’s great to have four million voters call you ‘Jimmy’ on Election Day, but it’s hell to have them living in your house for the next four years.’ In a nutshell, that’s why I couldn’t have been a better mayor, nor can anyone else.”

Sam Roberts writes obituaries for The New York Times and is writing a biography of Mayor Walker