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The corpse lay in a railroad yard in the Bronx, sliced nearly in half by a train. Nobody claimed the remains, and on September 13, 1913, city workers were readying the unknown dead man for burial on Hart Island, New York’s potter’s field. Municipal regulations required a final inspection of each nameless casualty, so a policeman lifted the coffin lid.

“Why, it’s Tim!” the cop said. “Big Tim!”

Timothy “Big Tim” Sullivan had been one of the most powerful, most beloved, and most corrupt politicians in New York City history.

Known as “King of The Bowery,” Sullivan served as a state senator, a congressman, and, most importantly, as boss of the Tammany Hall Democratic machine on Manhattan’s Lower East Side, where his reign combined politics, organized crime, and an emerging entertainment industry.

Timothy Sullivan was born in 1862 to impoverished Irish immigrants in Five Points, a lower Manhattan slum. His father died before the boy started school; his stepfather, a drunk, deserted the family, inspiring Tim to swear off booze for life. At eight, he was hawking newspapers in the street. At 18, he was running an outfit that distributed five newspapers across Manhattan. At 21, young Sullivan bought a saloon that functioned as headquarters for the Whyos, an Irish gang allied with the Tammany machine.

Soon, the youth was marshaling Tammany’s voter-fraud operation around The Bowery, using gang members to bully Republicans out of casting ballots and encourage  “repeaters” to vote often for Democrats. The best repeaters began Election Day full-bearded. “When they vote with their whiskers on, you take ’em to a barber and scrape off the chin fringe. Then you vote ’em again with side lilacs and moustache,” Sullivan said. “Then to the barber again, off comes the sides and you vote ‘em a third time with just a moustache. If that ain’t enough, and the box can stand a few more ballots, clean off the moustache and vote ‘em plain face. That makes every one of them good for four votes.”

Tall, brawny, and handsome, with bright blue eyes and a warm smile, Big Tim won election to the state Assembly in 1886 and in 1894 to the state Senate. His Bowery district was the city’s most crowded, elbow to elbow with Irish, German, Italian, and Jewish immigrants. Big Tim helped constituents get jobs, distributed coal, and bailed their kids out of legal trouble. At Christmas, he fed thousands a turkey dinner washed down with beer. Every February, he gave away shoes by the thousands of pairs. On Labor Day, he packed hundreds of families into riverboats for a free cruise to an amusement park. And all year long, Big Tim was a notoriously soft touch, handing cash to any petitioner with a tale of woe. All he asked in return was that on Election Day his people vote the straight Democratic ticket—twice, if possible. 

Spared a pauper’s grave by chance, Big Tim Sullivan departed via Old St. Patrick’s Cathedral, followed by “a procession of nations.” (Library of Congress)

Big Tim financed his good works Tammany style, through kickbacks and graft. Recipients of city jobs “donated” a tithe to Big Tim’s operation. So did businessmen anxious to avoid problems with city inspectors. City regulations required saloons and theaters to close on Sundays—for many customers, the only day off all week.

Publicans and impresarios could flout that law by splitting the profits with Big Tim’s machine. Pool halls, then illegal, paid $10 a day to stay open. Brothels and gambling dens ante’d far more. Big Tim personally pocketed at least $100,000 in graft a year, plus bribes paid him in Albany as a stalwart of the legislature’s infamous “Black Horse Cavalry,” a bipartisan caucus willing to kill bills for cash.

However, Big Tim did not live by graft alone. A shrewd businessman, he gazed upon The Bowery’s entertainments and saw the future. With one partner, he opened the Dewey Theatre, a Union Square vaudeville house. With another, he built a nationwide chain of vaudeville houses. He owned a piece of Coney Island amusement park Dreamland. He partnered with pioneering movie mogul William Fox in a chain of cinemas. An avid poker player, Big Tim invested in illegal gambling. Spotting a comer and hiring him to run one of his games, he told young Arnold Rothstein, “Gambling takes brains, and you’re one smart Jew-boy.” Sullivan had that right: in 1919 Rothstein made a fortune fixing the World Series.

In 1902, Tammany bosses offered to run Big Tim for Congress. “I’ll think it over,” he said. “If it ain’t a piker’s game, I might take a stack and
sit in.” When he ran, The New York Times denounced him as a “disreputable predatory politician” and “the embodiment of everything that is corrupt and vile.” Sullivan won in a landslide, served two terms, and quit, peeved at the paucity of graft available in the nation’s capital to a minority-party backbencher. “There’s nothin’ to this congressman business,” Big Tim said. “They use `em for hitchin’ posts down there.”

Sullivan happily returned to the New York state Senate, where graft was bounteous, and his Democratic colleagues included neophyte Dutchess County pol Franklin Roosevelt. When Roosevelt spurned an appropriation for his own district, saying it was unnecessary, Big Tim chewed him out. “Frank,” he said. “You ought to have your head examined.”

No statesman, Sullivan occasionally veered within range of the angelic. In 1911, appalled at gun violence in his district, he sponsored the “Sullivan Law,” which required a police permit to carry a concealed weapon. “I want to make it so that the young thugs in my district will get three years for carrying a dangerous weapon instead of a sentence in the electric chair,” Big Tim said. In 1912, he defied Tammany to help reformer Frances Perkins enact a law limiting the workweek for women to 54 hours. “I seen me sister go to work when she was only 14,” he told Perkins. “And I know we ought to help these gals.”

By then, the big fellow was sinking into mental illness. The deaths of his wife and a brother plunged him into depression. Muttering that enemies were doping his food, he lost 60 pounds. He spoke of suicide. Relatives took him to Europe, but a grand tour proved no cure, so his family committed Big Tim to a sanitarium. In April 1913, he moved in with his brother Patrick in the Bronx, becoming so violent caregivers straitjacketed him. In August, he ran off. He had been missing two weeks when a cop peeking into a coffin bound for potter’s field said, “Why, it’s Tim!”

Fame saved Tim Sullivan from a pauper’s grave. At his Bowery clubhouse, 20,000 people—many of them immigrants he’d helped—filed past his casket. “Behind the Irishman walked the Jew, the Italian, the Frenchman, the Scandinavian, the Chinese, the Spaniard,” the Times reported. “It was, in fact, a procession of all nations.”