On January 16, 1928, William Joseph Kennedy suffered a misfortune of birth only slightly preferable to bastardy. Having drawn his first breath, he studied his surroundings and found himself a newly minted Son of Albany. The gravity of his situation may have been lost on him, but not for long. By the age of reason, in the Catholic sense, he must have accepted the sordid truth of his paternity. Albany was a bookie and a gambler, a bootlegger and a dipso, a pimp and a john, a boss and a stooge. “Of all the miserable, wretched, second-class, one-horse towns,” wrote the architect Henry Hobson Richardson, “this is the most miserable.”

Albany was far from the action, halfway between Manhattan and the Canadian border. Where its political climate was strictly smoke-filled backroom, its actual one, much of the year, was walk-in meat locker. A youngster like Kennedy might don a cassock and surplice in the morning, quaking for his soul as an altar boy; survive a pointless fistfight at midday; bring his robes to the “Chinaman” for laundering in the afternoon; and at night hang around street corners or grocery stores, looking for a good chance to sin. It would have been a decent enough life, growing up in the shadow of Irish Catholicism and political corruption—but for a kid with ambition, who needed it?

In 1956 Kennedy lit out for San Juan, Puerto Rico, taking a position as assistant managing editor of the Puerto Rico World Journal. In 1959 he became a founding managing editor of the San Juan Star, where he was Hunter S. Thompson’s boss, and one can see Kennedy portrayed by Richard Jenkins, as “Lotterman,” in Bruce Robinson’s 2011 adaptation of The Rum Diary. In Puerto Rico, Kennedy found himself engrossed in a picture book of 19th-century Albany. He had to face it: “[San Juan] was not engaging my soul, and that Albany picture book was.” In 1963, he went back to Albany for good.

Ironweed, the 1983 novel that made Kennedy’s name—it won the Pulitzer Prize the next year—is about a man returning to Great Depression-era Albany at Halloween. Though he bears no resemblance to Kennedy, Francis Phelan, a guilt-wracked, alcoholic hobo, illustrates how a man becomes magnetized to home, despite the compelling reasons to get lost. As the story begins, Francis, “[r]iding up the winding road of Saint Agnes Cemetery in the back of the rattling old truck . . . became aware that the dead, even more than the living, settled down in neighborhoods.” The neighborhoods of men and memory, the ever-changing anima of a city, are Kennedy’s perennial subjects, and never more explicitly than in the other book he published in 1983, the essay collection O Albany! Improbable City of Political Wizards, Fearless Ethnics, Spectacular Aristocrats, Splendid Nobodies, and Underrated Scoundrels.

Kennedy’s remarkable project began in 1963, when an Albany Times-Union editor, Walter Hawver, asked Kennedy for a series showcasing the city’s neighborhoods. This Kennedy completed between 1963 and 1964. Later, revisiting those pieces at the request of Albany’s Washington Park Press, he “found them all misshapen by time and their prose as flat as Mesopotamian root beer.” Thanks to his insistence on revising them, what might have been a very minor, parochial pamphlet—the sort of thing you fan yourself with at the Historical Society—became a detailed portrait of America in microcosm, and proof that a penetrating eye can turn a one-horse town into a metropolis deserving of its place in posterity.

In his overture, “Albany as a State of Mind,” Kennedy calls his project “an attempt to strike a balance as to Albany’s legend. Even iniquity has its charms: consider what Milton did with Satan.” Nothing in Kennedy’s Albany is sentimentalized, trivialized, romanticized, or demonized. He confers dignity on vagrants and prostitutes without turning them into glowing unfortunates. He can mull the causes and effects of political corruption without assuming the mantle of a thundering reformer. He was, after all, a reporter before he was a novelist, and the essays in O Albany! are products of a fact-finding mission that transformed into a newspaper position and in turn into a life’s work. Here, then, are some of the things he demanded to know:

Stefan Beck is a contributor to CJR.