William Kennedy was born in Albany, New York, in 1928. He began a career in journalism working as a sports reporter in Glen Falls at the Post Star. He was drafted in 1950 and began working for an army newspaper in Europe. After being discharged, he worked for the Times-Union in Albany until 1956, when he moved to Puerto Rico, where he studied under the writer Saul Bellow. In 1959, he became the managing editor of the San Juan Star, but quit two and a half years later to write fiction full time. He moved back to Albany in 1963, and wrote a series of articles about the city that garnered him a nomination for the Pulitzer Prize. These articles formed the foundation for his nonfiction book, O Albany!. Kennedy went on to write three novels about Albany, the first of which is Legs.Billy Phelan's Greatest Game and Ironweed, which won the Pulitzer Prize in 1983, followed. Kennedy's "Albany cycle" has been lauded as a singular literary achievement of twentieth- century America.

Legs tells a fictionalized version of the story of Jack "Legs" Diamond, was a real gangster who deserted the army, bootlegged liquor, and survived four shootings. During prohibition, Jack moved to Greene County, New York with his wife, his mistress, his gang, and his bodyguard. For a time he was adored by both the press and the public. A newspaper article announcing his death suggested that the killers found the elusive Legs by trailing his mistress, Kiki Roberts.

In one sense, Legs is the story of an infamous criminal who has spent most of his life cheating people, stealing, seducing women, laundering money, and dealing drugs. Legs is also a tale chronicling the fall of the storybook underworld scene of Prohibition America, a time when a puritanical law banning alcohol incited a great social revolution. Americans imagine the time detailed in Legs as an idyllic period of speakeasies on every street corner ruled by mobsters with charming nicknames and intimidating submachine guns, a period when Bonny and Clyde, Al Capone, and hardened private eyes thrived. Jack was in the newspaper headlines almost every day during this period. Despite his reputation for heartless violence, Jack was revered by the people of upstate New York, and, indeed, by the whole country. Prohibition made it cool to be bad, like Jack was.

By the time Marcus Gorman, the novel's narrator, became Jack's lawyer, the era of romanticized gangsters had begun to fade. The repeal of prohibition was just around the corner, as was the Great Depression, a time that made the lavish excesses of the previous decade seem like a mistake. Jack still held sway over the local imagination in upstate New York, which allowed him to win his two trials there. But he did not have a chance against the federal agents. The official rhetoric of the state turned against the gangsters and against Jack in particular. Marcus had a difficult time trying to muster political support for Jack. Marcus's Republican connection, Van Deusen, warned him that the political tide was turning against Jack's kind. The end of the novel sees the end of the prohibition rebellion.