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Hylan was born in 1868 in Hunter, New York. He was the first son and third of five children of Thomas H. and Juliette (Jones) Hylan. His father, a Civil War veteran and a debt-ridden upstate New York farmer, had come to the United States from Ulster, Ireland, at the age of seven. On his mother's side, Hylan's grandfather was of Welsh birth, his grandmother a descendant of Jacob Gadron, a French soldier who came to America with Lafayette during the Revolutionary War.
With his wife's encouragement, Hylan attended Long Island Business College at night to prepare himself for law school. While still a railroad employee he became a clerk in the law office of James T. Olwell and managed to complete the course requirements at the New York Law School, from which he received the LL. B. degree in 1897.
After working for a time on a nearby railroad, he left home at the age of nineteen and arrived in Brooklyn with only a dollar and a half in his pocket. He soon obtained a job as track layer and later as fireman on one of the city's steam-driven elevated railroads. Two years later he was promoted to be engineer.
Hylan began his law practice in partnership with Harry C. Underhill in the Bushwick section of Brooklyn, where he also became a Democratic party worker. In 1905 his party nominated him for justice of the municipal court, but he was defeated. In the following year he called the attention of Mayor George B. McClellan to a forgotten law which required the appointment of two additional magistrates in Brooklyn. With McClellan's approval Hylan brought a successful mandamus proceeding to compel the mayor to fill these posts, receiving one of them himself. In 1914 Gov. Martin H. Glynn appointed him a judge of the Kings County Court, and in 1915 he was elected to a seven-year term on the same bench.
Hylan was still a relatively obscure person when in 1917 he was picked by Tammany Hall as its candidate for mayor. His selection was largely the result of his political association with the newspaper publisher William Randolph Hearst, at that time influential in New York City Democratic politics. Hearst had supported the incumbent reform mayor, John Purroy Mitchel, in 1913 but had broken with him and become his most virulent opponent. As the election of 1917 approached, Alfred E. Smith was the Tammany favorite for the nomination, but Boss Charles F. Murphy, anxious to consolidate the opposition to Mitchel, passed him over for Judge Hylan as a means of conciliating Hearst. Hylan's campaign charged Mitchel with being the tool of the business interests. Under Mitchel the "Gary system, " a plan of school organization developed in Gary, Ind. , by William A. Wirt, had been introduced into some of the New York City schools. This Hylan attacked as a scheme of "the Rockefeller interests" to keep the children of the poor in the working classes by denying them a liberal education. Rockefeller interests were also accused of controlling the transit companies and the gas and electric companies. "My fight, " declared Hylan – in a campaign in which the Socialist candidate, Morris Hillquit, threatened to draw a substantial vote – "is to take from the hands of monopoly the control of our public utilities and to administer them for the profit of all the people". World War I played a part in the confused campaign, for Mitchel's zealous support of preparedness measures, both before and after United States entry into the war, as well as his attacks on his opponent as pro-German, helped to consolidate New York's large Irish and German elements behind the Tammany candidate. Hylan defeated Mitchel by a vote of more than two to one.
In office Hylan was frequently embroiled in controversy. His appointees, often obscure persons who had befriended him during his youth, were not well received by the press. Indeed, his relations with the press (always excepting the Hearst papers) were poor. As mayor, it was said that he gave the patronage to Tammany and the policies to Hearst. For a time, at least, this division achieved its desired result. The Malbone Street subway wreck (1918), in which ninety people were killed, gave Hylan a chance to intensify his attacks on the traction and public utility interests. He was renominated in 1921 and easily reelected.
Hylan's second term was even more replete with controversy than his first. He and Comptroller Charles L. Craig were at swords' points throughout his second term. In 1921 Hylan's grant of a permit for a pro-German meeting to be held in Madison Square Garden brought demands from the American Legion for his removal from office. Perhaps to offset this, perhaps following the lead of the Hearst press, Hylan soon afterwards launched an investigation into allegedly "pro-British" American history textbooks in the city's public schools. More constructively, he pushed through a substantial school-building program.
Hylan's two terms as mayor were principally noteworthy for the city's commitment to municipal operation of the third major division (the Eighth Avenue or Independent line) of the city subway system. He made the five-cent subway fare so potent a political shibboleth that for more than twenty years no mayor dared to change it. With the death of Boss Murphy in 1924 Al Smith became the dominant figure in Tammany Hall. Smith had supported Hylan in 1921, but a subsequent rift between Smith and Hearst left Hylan's position as a Hearst adherent insecure. In 1925 the Tammany leadership announced its refusal to support the renomination of Hylan and its sponsorship instead of James J. Walker. Hylan contested the decision but lost in the primary.
Mayor Walker subsequently (1930) appointed Hylan a justice of the children's court in Jamaica, Long Island, N. Y. , a position he held until his death. In 1934 Hylan ran for governor of New York as a candidate of the Recovery party. He died at his home in Forest Hills, Long Island, of a coronary thrombosis and was buried in St. John's Cemetery, Middle Village, Long Island. He was survived by his only child, Virginia, the wife of John F. Sinnott, son of a prominent Brooklyn Democratic leader.
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Though Hylan's mother was a Methodist before her marriage, the boy was brought up in his father's faith as a Roman Catholic.
Quotations: In the somewhat severe judgment of New York Park Commissioner Robert Moses: "Hylan, self-educated, dull, plodding and transparent, was a decent political hack, picked because he was the most pliable, respectable material that could win without effort. " In the City Hall he "swelled instead of growing . " On the other hand, as James A. Farley remarked, "No one ever questioned his honesty of purpose or his sincerity. "
While most people found Hylan a kindly, modest person in private life, many felt that he lacked the innate ability for high office.
On September 24, 1889, married his childhood sweetheart, Marian O'Hara (who later used the name Miriam Louise Hylan).
