The not-so-brief history of scandal among New York City mayors

As federal agents conducted an early morning search of Gracie Mansion on Thursday, the name “Elegant Oakey” was probably not foremost in their minds. It sounds like a hot tip running the third race at Aqueduct Racetrack, or a retro speakeasy feigning authenticity on the Lower East Side.

But that search of the New York City mayor’s official residence, part of a large-scale corruption investigation, has resurrected the curious name of A. Oakey Hall from Gotham’s distant past. For the last 150 years, Hall, a mayor from the Boss Tweed era whose style earned him the sobriquet of Elegant Oakey, held distinction as the only New York City mayor to face criminal charges while in office.

He now has company.

Mayor Eric Adams has become the second sitting mayor of this city to be indicted, and the first since the consolidation of the five boroughs in 1898 made New York City what it is today. He is also the first to face federal charges. The indictment Thursday charged that over the last decade, including during his years as Brooklyn borough president, Adams “sought and accepted improper, valuable benefits.”

This is the latest in a series of troubling developments that secure the Adams administration’s place in the annals of New York municipal scandal.

The mayor and his administration join Mayor James. J. Walker, who, like Adams, enjoyed the nightlife. And Mayor William O’Dwyer, who, like Adams, was a former police officer. And Mayor Ed Koch, who, like Adams, was said to have placed too much trust in others. And of course, A. Oakey Hall, who, like Adams, was known for his fashion sense.

“There’s barely a mayor in history who didn’t have a scandal at one time or another,” said Chris McNickle, the author of several books about New York City mayors. “Sometimes the scandals overwhelm and swallow the mayors. And sometimes they’re able to skate around it successfully.”

Whether Adams will skate or be swallowed remains to be seen. But the breadth of the investigations — there are four separate federal inquiries alone — cannot be good for his legacy or, more important, for the psyche and operations of the city.

“Over the next year we’re not going to be talking about housing or education or the migrant crisis,” said Terry Golway, a professor of history and political science at the College of Staten Island. “We’re going to be talking about what did the mayor know, and when did he know it. And that will cast a shadow over the city.”

The federal indictment charges Adams with bribery, fraud and soliciting illegal foreign campaign donations. The benefits he is said to have received are valued at more than $100,000 and include free and discounted Turkish Airlines tickets, meals and hotel rooms. In return, prosecutors said, the mayor compelled the Fire Department to tiptoe around safety concerns to approve a new high-rise Turkish consulate in midtown Manhattan.

Adams has been defiant in asserting his innocence. He has called for a quick trial and a resistance to rushed judgment. “I ask New Yorkers to wait to hear our defense,” he said Thursday.

But the other inquiries, so numerous and so intertwined, have led investigators to the doorsteps of those who preside at the top of city leadership: close friends and associates handpicked by Adams to help him run this complex metropolis. The police commissioner has resigned. The schools chancellor has announced he’ll do the same, while his partner — the first deputy mayor — and his brother — the deputy mayor for public safety — have both had their phones seized. So has another old friend and top aide.

Whether the mayor’s actions are rooted in a sense of loyalty or of entitlement, they have placed him in a dubious wing in the echoing halls of posterity, alongside tainted mayors who came before him.

Koch, a Democrat who served from 1978 to 1989, was an unabashed reformer who struck pacts with several political bosses to secure his first election. He seemed to personify the city’s charisma and chutzpah; that is, until 1986, when a suicide attempt by a political ally led to revelations of corruption in the Transportation Department and the Parking Violations Bureau, among other city agencies.

Dozens were convicted. While Koch was never accused of financially benefiting from the graft, he was criticized for allowing cronyism to taint city operations. Knowing that his legacy had been compromised, he became deeply depressed, at one point even considering suicide.

Timing in politics, as in life, matters. Just as Adams is grappling with formidable challenges — an influx of asylum-seekers, a lack of affordable housing and a struggling school system, among others — so too was Koch dealing with rises in crime rates and racial tensions.

“The corruption fed into a broader sense that things were out of hand,” said Mason B. Williams, a professor of leadership studies and political science at Williams College. “It’s fair to say that New Yorkers become less tolerant of misgovernment when there are pressing social and economic issues to deal with.”

Maintaining that the charges against him are rooted in lies, Adams pleaded not guilty Friday. He has refused calls for his resignation that began even before his indictment. But if he were to resign, he would join an exclusive club: Only two New York mayors have resigned in the midst of allegations of corruption — and both seemed to have had little choice.

Walker, the dapper, witty mayor who presided over New York City from the mid-1920s and into the Great Depression, often ran the city from a women’s refreshment station in Central Park that had been converted into a chic nightclub. There he could meet chorus girls and hobnob with Tammany Hall cronies.

But the graft was so rampant “that you were almost required to be corrupt,” said historian and novelist Kevin Baker. “The systemic corruption was amazing, yet routine.”

A legislative investigation into the corruption came at an inopportune time for the governor, Franklin D. Roosevelt, who was running for president. Walker, who admitted to receiving what he called “beneficences,” resigned under pressure in September 1932 and promptly left for Europe. He was never indicted.

Less than 20 years later, yet another mayor left the country. William O’Dwyer, who served from 1946 to 1950, was an Irish immigrant who, as a police officer and then as Brooklyn district attorney, built a reputation as a crime fighter. But he also had associations with organized crime figures.

And, like Adams, he maintained close ties with some of his law-enforcement colleagues, which proved damaging when a few were implicated in a police corruption scandal involving protection payoffs by a large-scale bookmaking operation.

O’Dwyer had heart problems, and he sometimes complained about the never-ending demands on New York’s mayor. Whether to save his heart or his skin — or the electoral possibilities of the Democratic Party — he abruptly resigned in 1950 to accept President Harry Truman’s surprising offer to become ambassador to Mexico. And off he went.

But there was only one A. Oakey Hall, a slight, fastidious man with a penchant for puns and a taste for trying to “out-Herod Herod,” as one biographer put it, in his sartorial tastes.: pince-nez, custom-made frieze coats with velvet collars, high-quality linen shirts, brightly colored vests and fine silk ties.

A successful lawyer and prosecutor who enjoyed the spotlight, Hall hitched his fortunes to the Tammany Hall of the 1860s, and therefore to its boss, William Marcy Tweed, the undisputed master of enriching himself at the expense of the public.

The costly monument to Tweed corruption is at 52 Chambers St., commonly known as Tweed Courthouse but now the headquarters for the Department of Education. The city spent nearly $13 million — or about $300 million in today’s dollars — on a building that should have cost considerably less. But fraudulent bills submitted for work never done, by people who sometimes didn’t exist, provided a fire hose of money for Tweed and his gang, with Hall signing the necessary paperwork without pausing to consider the discrepancies and cost overruns.

Detailed revelations in The New York Times exposed the Tweed Ring, prompting national outrage. “It will all blow over,” Hall told a reporter. “These gusts of reform are wind and clatter.”

But the winds of reform kept blowing. In early 1872, after weeks of whispers about impending criminal charges, Hall was indicted — charged, effectively, with willfully neglecting his official duties.

Like his distant successor, Adams, Hall adamantly maintained his innocence. And, like Adams, he insisted that a trial be held immediately.

The illness of a juror led to a mistrial. Eager to be vindicated before the end of his term, Hall continued to advocate for speed, only to have his second trial end in a hung jury.

Convicted and defeated, Tweed died in prison in 1878. Hall was acquitted after a third trial. He then took to the stage, spent years in London and resumed his New York law practice before dying at the age of 72 in 1898.

On the day his mayoralty ended, at the dawn of 1873, Hall welcomed his successor to City Hall and shook his hand. At that moment an aide brought in a pile of mail concerning the affairs of New York City.

Seeing that the letter on top was from the city coroner’s office, Elegant Oakey said the truest of words: “I think that letter should have been addressed to me, for I am the dead mayor.”

This article originally appeared in The New York Times.