“Why was I an only child in a vast family of brothers and sisters and untrackable cousins? . . . Why did my uncles marry so late or not at all? Was there such a thing as culture in Albany? Could you get rich without being in politics? Who was this Van Rensselaer fellow? Why was Eddie Carey called the Squire of North Albany and what precisely was a squire in Albany’s lexicon and why did Eddie live at the top of Van Rensselaer Boulevard and why had I always lived at the bottom in one of his houses? Why was the North End, my neighborhood, almost exclusively Catholic, and Irish, and Democratic?”

Kennedy’s intention was to answer a few of those questions—to learn more about “the city’s ethnic blueprints, its political history and the nature of its peculiar people”—but probably not to be consumed by them. Fate, and Albany, had other plans.

O Albany! is divided not chronologically but into six sections of loosely associated essays. The first and last, “The Magical Places” and “Closing Time,” are the loosest in this regard. The former serves to familiarize the reader with Kennedy’s avowed Albany boosterism; the latter consists of acknowledgments and parting reminiscences. The middle sections get right to the point. “The Neighborhoods” is a thorough guided tour. “Nighttown” is a trio of essays about the fine distinctions between a “sport” and a “swell”; how Albany negotiated Prohibition; and the murder of Jack “Legs” Diamond, Albany’s favorite gangster. The “fearless ethnics” who appear in Part Four, “Some of the People,” are Jews, Italians, Germans, and Blacks—the Irish being segregated in Part Five, “Long-Run Politics: Wizardry Unbound.”

This patchwork is a vastly more interesting way to learn about a city than the traditional chronological history, but it presents two difficulties. One is that the individual essays tend to jump around in time, and not just because Kennedy is writing about neighborhoods and institutions down through the decades. Almost as often, it is a function of his style, which is pleasingly torn between the journalistic and the literary, the present-day and the poetically historical. This tension of styles and techniques means that everything in O Albany! happens out of anything like order, and however vivid a sense of Albany the reader walks away with, he will never have a prayer of explaining the city’s chaotic progression from a “primeval and savage wilderness” opened up by “those agents of the first Patroon, and the Dutch West India company pioneers” to whatever shape Kennedy found it in in 1983.

The second difficulty is related, and similarly forgivable on the grounds that a great book is preferable to a merely educational one. As Kennedy has eschewed a chronological trudge, he is free to allow his own preoccupations, literary and personal, to guide his investigations. His account leans heavily on three famous Albanians: Erastus Corning 2nd, Daniel Peter O’Connell, and Jack Diamond. To know these names and what they mean is to know, perhaps, enough about Albany—and certainly enough about Kennedy’s Albany—even if they belong to just one century of its long history.

It is not unusual to hear in 2012 about machine politics, though the preferred phrase, for obvious reasons, is “Chicago-style politics.” Whether the latter term endures because Albany has been overlooked or because it has been let off the hook is a matter of speculation. The fact is that Chicago’s Mayor Richard J. Daley served from 1955 to 1976, and Albany’s Mayor Erastus Corning 2nd was first elected in 1941 and made it to 1983, the auspicious year of O Albany!’s publication. That’s eleven terms. Though the record never made it into Guinness, it did wind up in Ripley’s, in July 1982, alongside “nineteen wingwalkers and a chicken that laid eggs for 448 straight days, believe it or not.”

The boss of Albany’s Irish-Democratic political machine was Dan O’Connell, who had grown up with Mayor Erastus’s father, Edwin, making Dan and Erastus’s “eventual union in politics . . . really the extension of a long friendship”—a family friendship, in any case, or even an existing alliance. Kennedy’s essays “The Democrats Convene” and “They Bury the Boss: Dan Ex-Machina” form an operating manual for machine politics. What did the machine provide? “[T]he job, the perpetuation of the job, the dole when there was no job, the loan when there was no dole.”

Stefan Beck is a contributor to CJR.