New Yorkers have elected few mayors as individualistic as William J. Gaynor, who became the city’s 94th chief executive on January 1, 1910. Prior to becoming mayor, Gaynor practiced law, having been admitted to the bar in 1871. His clients included such characters as “Shifty” Hughie McCarthy who, as Gaynor biographer Lately Thomas wrote, was “always in trouble, suspected of everything, and usually guilty.” Gaynor’s investigation of election frauds led to indictments, convictions, and his 1893 election to the state Supreme Court.

A staunch libertarian, Gaynor was described by the New York Globe as “…a primitive American (who) really believed in the Bill of Rights.” Realizing that men were unlikely to become angels simply due to changes in the rules, he was impatient with those who abused the law to impose their morality on others. He particularly opposed Sunday closing laws, which denied the public entertainment on their day off and discriminated against observant Jewish merchants. Gaynor was often impatient when expressing his views: Longtime City Hall reporters agreed hands-down that his capacity for epic, imaginative profanity, rich with allusion, imagery, and metaphor, made Fiorello La Guardia’s volcanic tantrums look silly.

But if a reporter caught Gaynor on a good day, the judge would grumble, “Well, let’s go to work on it like mechanics,” take out two tumblers, and uncork the Old Senator. With friends he was a conversationalist, and he loved dining with them over champagne, talking about history, literature, the law, or whatever else came to mind. Ira Bamberger, a lawyer and friend, remembered once talking with the judge well into the night, with more than one bottle emptied. He was scheduled to plead a case before Gaynor the following morning and, atrociously hung over, staggered in late. The judge dryly rebuked him from the bench, concluding, “From your appearance, you would seem to have fallen among bad companions.”

In 1909, Tammany boss Charles F. Murphy, hard-pressed to keep City Hall, nominated Gaynor for mayor – somehow believing he could be controlled. Victorious after a rough campaign, his relationship with Tammany soured because Tammanyites believed political support entitled them to all jobs while Gaynor disregarded party ties to appoint qualified officials. “What do we have for Charlie Murphy?” a colleague once asked. “A few kind words,” Gaynor replied.

The mayor’s tart correspondence made him famous: “Dear Sir: I care nothing for common rumor, and I guess you made up the rumor in this case yourself. Very truly yours, W. J. Gaynor, Mayor.” “Dear Sir: Your letter is at hand and I have read enough of it to see that you are a mere scamp. Nonetheless, I sometimes derive profit from the sayings and doings of scamps.” “Dear Madam: I regret to say that I do not know anyone I can recommend to you as a husband. You can doubtless make a better selection than I can, as you know the kind of man you want. Of course, it may be very hard to find him, but no harder for you than for me.” “Dear Sir: No, I do not want a bear.”

In August 1910, Gaynor, about to depart for a European vacation, was chatting dockside when a recently fired city employee, James Gallagher, rushed up shouting, “You have taken away my bread and butter,” and shot him in the back of the neck. A New York World photographer kept snapping pictures, characterized thus by editor Charles Chapin: “Blood all over him, and an exclusive, too!” Gaynor barely survived and never fully recovered.

Unfortunately, Gaynor’s police commissioner Rhinelander Waldo was clueless. Waldo’s chief of staff was on the take from “Big Tim” Sullivan, one of the triumvirate controlling the city’s illegal gambling. Another gambler, Bald Jack Rose, paid vice squad Lieutenant Charles Becker $640,000 within 10 months – about $10 million today. Frustrated small-timer Herman Rosenthal told the New York World about his partnership with Becker in illegal gambling. Two days after the story broke on July 14, 1912, Rosenthal was murdered. Although Becker apparently had known nothing of the hit, he was convicted and executed for Rosenthal’s murder on July 30, 1915.

The established parties rejected Gaynor’s candidacy for re-election in 1913. He ran as an independent, insisting he would “shovel all these grafters into the ground.” He took a brief vacation in early September before launching his campaign. On September 12, 1913, as his liner neared the Irish coast, Gaynor’s son bent down to his father, who was reclining in a deck chair, and found him dead. Eight days later, Gaynor lay in state at City Hall. Five hundred people were waiting when the doors opened, followed throughout the day by tens of thousands of ordinary New Yorkers who paid their respects to honor one who, whether right or wrong, had always been on their side. At midnight, 20,000 were still waiting in line.

His official portrait in City Hall is hidden behind the door to Room 9, the Press Room.