Law career Hylan learned that law practices required startup cash, so he mortgaged the farm again to raise $500. With that sum, he set up an office on the corner of Gates Avenue and
Broadway in Bushwick. He made $24 his first month, but gradually built up a good civil litigation practice. He soon formed a partnership with Harry C. Underhill, an attorney who had written a treatise on evidence and would go on to write on other practice topics. Underhill did the office work, while Hylan was the trial lawyer. The firm occasionally received positive local publicity, such as the time when they obtained a ruling that the
Brooklyn Heights Railroad Company had to offer free transfers at all junctions. Hylan litigated small civil cases and family law matters. He had little work in the police courts and "never cared for that branch of the law." After eight years in the courts of Brooklyn, he was respected enough to begin getting appointments within the power of local judges. Hylan had higher ambitions, so he began making the kind of connections expected of someone considering a run for higher office. One connection he made, albeit by accident, was
John H. McCooey, the future Brooklyn Democratic Party boss; they met when McCooey was a postal clerk and Hylan was sending money orders to his parents for interest payments on the family farm's mortgage. Hylan would remain grateful for the kindness McCooey showed him, and they remained friends thereafter. Other contacts were made by constant attendance at local organizations, political and otherwise. In addition to his union membership, which he kept up even when he was mayor, he was a member of the Foresters of America, the Broadway Board of Trade, the Twenty-eighth Ward Taxpayer Association, and he began working his way up the local Democratic club.
Politics and judgeships Hylan emerged from obscurity in Brooklyn Democratic politics during the citywide elections of 1903, a campaign during which several internal Democratic power struggles worked themselves out. In Manhattan
Charles Francis Murphy had recently replaced
Richard Croker as head of the Tammany machine. Murphy, who had become independently wealthy from a trucking company which leased docks from the city and rented them to shipping companies, fixed his goal as Tammany chief to extend Tammany influence to all the boroughs and then beyond. He decided to dislodge Fusionist mayor
Seth Low by running
George B. McClellan Jr., son of the
Civil War general who had run against
Lincoln in 1864. The move was unpopular in Brooklyn, whose leaders believed that McClellan would hurt down-ticket Brooklyn candidates; they concluded that running McClellan likely would cost them the district attorney and sheriff's offices, not to mention borough and judicial races. Murphy's highhandedness rankled others as well. At the City Committee meeting on September 18, party leaders from Queens, the Bronx and Richmond joined Brooklyn in expressing their concern. Independent Manhattan Democrats also objected to Murphy's action, including the Greater New York Democracy, which decided for the Fusion ticket, and former Tammany police chief
Bill Devery, who decided to run for Mayor himself. Even several Tammany chiefs questioned the wisdom of the McClellan choice. Brooklyn party leader
Hugh McLaughlin decided to test Murphy's hold over the outer boroughs and gave an interview promising to oppose Murphy's nominee at the city convention. With a view to sowing confusion among the Fusionists, Murphy without consultation outside of Tammany proposed adding two Fusion candidates to the ticket—Edward M. Grout for Controller and Charles V. Fornes for President of the Board of Aldermen. The proposed nomination of two Fusion candidates by Tammany so disturbed the non-Tammany Democrats that, after much behind-the-scenes scheming, McLaughlin announced a complex plan the day before the convention to either dislodge McClellan from the ticket and Murphy from Tammany in the process or provide an anti-Tammany Democratic ticket that would run against Tammany's ticket. The convention took place on October 1, 1903 at Carnegie Hall. At the beginning it looked as if the Kings County delegation could engineer a stampede against the Tammany ticket. Brooklyn Assistant District Attorney
Martin W. Littleton led the charge, looking directly at Murphy in front of him and delivering a blistering speech scoring Tammany "treachery" for selecting Democratic "traitor" Grout. Robert H. Elder followed him, placing in nomination Julian D. Fairchild in Grout's place and reminded the convention that Grout had been a Republican and left the Brooklyn Democrats because of their association with Tammany. Littleton rose again to remind the delegates that Grout once called Tammany a "stench in his nostrils." The "excitement reached a climax" when one Tammany leader broke with Murphy against Grout causing "wild applause." The next day at the Brooklyn Democratic headquarters in the auction room on Willoughby Street, all talk of McLaughlin's plan for an opposition ticket to Tammany's had ceased. If McClellan won the mayoralty, all Brooklyn patronage would go through him and Tammany. While Brooklyn maintained its objection to Grout and Fornes, that did little good for the Brooklyn party unless McClellan lost, but McCarren and the rest at the Convention eventually endorsed McClellan. As one Democrat put it: "Tammany's coming to Brooklyn sure and the Old Man [McLaughlin] will take his medicine." For McLaughlin whether he would remain in charge of the Brooklyn Democrats now depended on his former subordinate McCarren. McCarren, however, used the occasion to take over the Brooklyn organization, and in the turmoil Hylan made his first move for party advancement.
Mayor of New York City at
Ebbets Field. Hylan defeated the reformer
John Purroy Mitchel in the four-sided 1917 mayoral election, restoring the power of Tammany at City Hall. Hylan was the first Democratic candidate to obtain a significant portion of the
African American voter base. He easily won re-election in 1921 but was defeated for re-nomination in 1925 by State Senator
James J. "Jimmy" Walker. Walker later appointed Hylan to the municipal judiciary. The
Hylan Boulevard in
Staten Island was renamed for him in 1923 over the protests of his political opponents. Hylan developed a reputation for not being exceptionally intelligent or well-spoken. According to
Robert Moses, Hylan went through most of a mayoral campaign using just one stump speech: a call to keep the five-cent
subway fare in place. He asked for Moses' help in preparing another, and Moses obliged. The first time Hylan tried to deliver the new speech, he reached the climax—a
Revolutionary War-inspired "I call for the spirit of 1776"—but rather than closing out on a high note, Hylan missed the context and read out the number's digits, saying, "I call for the spirit of one-seven-seven-six." In another story recounted about Hylan's supposed lack of intelligence and articulateness, his successor
Jimmy Walker appointed Hylan as judge of the Queens Children's Court. When journalist
Alva Johnston asked Walker why he would appoint a rival to a judgeship, Walker quipped, "The children now can be tried by their peer."
Famous speech Hylan's most famous statement against "the interests" was the following speech, made in 1922, while he was the sitting Mayor of New York City: ==Death==