As mayor he was noted as a reformer who broke ranks and refused to take orders from the Tammany boss Charles Francis Murphy.

The Gaynor family were Irish and devout Catholics, thus, when weather permitted, on Sundays they would head to the nearby city of Utica to attend Mass at St. John's Church on Bleecker Street.

As William entered his teenage years, he began to show a religious fervor that led his parents to think that he might have a vocation to the Church.

As a result, however, by the time the small group of Brothers had arrived at their destination, Gaynor had lost his belief in organized Christianity and had decided to leave the institute.

This was to be the start of his entry into the political arena, as Horatio Seymour had recently served as Governor of New York, and had just run as the Democratic Party's candidate for president against Ulysses S.

Elected to the New York State Supreme Court in 1893, and appointed to the Appellate Division, Second Department in 1905, Gaynor's rulings were often cited around the country.

Gaynor's marriage with Tammany Hall was short-lived; soon after taking office, he filled high level government posts with experts and city employees were chosen from civil service lists in the order they appeared, effectively curbing patronage and nepotism.

"[11] H. L. Mencken, who covered the police beat and City Hall of Baltimore in his early days as a reporter, and so learned to know the good, the bad and the ugly of the species, had great respect for Gaynor both as a judge and as mayor.

He turned loose hundreds of prisoners, raged and roared from the bench, and wrote thousands of letters on the subject, many of them magnificent expositions of Jeffersonian doctrine.

When Tammany, with sardonic humor, made him mayor, he began an heroic but vain effort to give New York decent government....In the end, worn out and embittered by the struggle, he died unlamented, and today political historians scarcely mention him.

"[12].Gaynor read the first edition of Henry George's famous treatise Progress and Poverty said that Georgism was the "perfect" and "optimal" system ("admitted by philosophers and economists the world over").

[13] Early in his term, Gaynor was shot in the throat by James J. Gallagher,[15] a discharged city employee who had been a New York dock Night Watchman from April 7, 1903, to July 19, 1910.

The violent incident happened on board the Europe-bound SS Kaiser Wilhelm der Grosse, which was docked at Hoboken, New Jersey.

[18] Observing Gaynor in conversation, New York World photographer William Warnecke snapped what he thought would be a typical, if uneventful, photo of the new Mayor.