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 on Thursday charged that over the last decade, including during his years as Brooklyn borough president, Mr. 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 Mr. Adams, enjoyed the nightlife. And Mayor William O’Dwyer, who, like Mr. Adams, was a former police officer. And Mayor Edward I. Koch, who, like Mr. Adams, was said to have placed too much trust in others. And of course, A. Oakey Hall, who, like Mr. 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.”