O’Connell got his start in politics after being elected tax assessor in 1919, and abuse of the assessor’s office played a major role in the machine’s control: Back a non-Democratic candidate for any office and one might find the assessment on his property higher than expected. Electoral fraud was, naturally, in the natural order of things:

One city water inspector was arrested passing out envelopes to voters at a polling place, and when searched he had 45 envelopes in his pocket, each containing $4. This looked rather like a man purchasing votes. But he said he was contributing to a charity fund to buy food and shoes for needy folks and the polling place was the best spot to find them. He was released, probably because such ingenuity could not go unrewarded.

At Dan O’Connell’s funeral, “only if you were seventy-nine years old . . . could you have voted for a Democratic candidate for mayor of Albany who hadn’t been of Dan’s choosing.” He and his longest-serving mayor had survived Governor Thomas Dewey’s corruption investigations. Corning had survived service in World War II—during a mayoral term. If these men had a lock on Albany politics, it was in part because Albanians encouraged it.

It is easy enough for a journalist to loathe corruption, even corruption that keeps the peace or keeps the people happy. It is harder for a novelist. The journalist Kennedy “[wrote] stories that complicated [the Mayor’s] life.” The novelist Kennedy was delighted when the Mayor approached him to collaborate on a book in which Kennedy would be able to say whatever he liked, as would Corning. The book never came to fruition, but an essay, “Erastus: The Million Dollar Smile,” did. The result is an excellent example of Kennedy’s candid, psychologically astute, and above all sympathetic portraiture. The essay gets to the heart of Kennedy’s essentially novelistic journalism. Whether because he retains some vestigial sense of Original Sin, or simply because he grasps human folly, he is capable of regarding any man as an equal, a potential friend, and certainly a fascinating subject for study—no matter how wicked.

Kennedy never met the gangster Jack Diamond, but one guesses he would have held his own there, too. Diamond, a Prohibition-era rumrunner, hijacker, and bootlegger, was killed under mysterious circumstances inspected carefully by Kennedy in “The Death of Legs Diamond.” Diamond’s criminal career, romantic life, and death are also given a monumental treatment in Kennedy’s novel Legs. The novel, narrated by Diamond’s lawyer, is a valuable study of how seductive a legendary figure can be, even if he is evil. The Diamond of Kennedy’s essay is a much smaller and uglier character, albeit still fascinating. To read the two treatments side by side is a lesson in how facts may undergird a novel, but, more important, in how to take the shine off a legend when dealing in reality.

Nowadays, rare is the work of nonfiction without a subtitle chugging across its jacket as long and noisy as a passenger train. O Albany!’s is as long and noisy as the worst of them, but it may be forgiven—partly because Kennedy was something of a pioneer in this, and partly because nobody would buy a book with “Albany” in its title unless it bore a subtitle promising the sensational. The trouble with Kennedy’s Political Wizards, Fearless Ethnics, Spectacular Aristocrats, Splendid Nobodies, and Underrated Scoundrels is that it omits an important class of characters. Albany’s great buildings, in Kennedy’s telling, have a life of their own.

Take Union Station: In “The Romance of the Oriflamme,” Kennedy writes that it “was magical because it was more than itself, which is how it is with any magical man, woman, or building.” Kennedy ponders it from the vantage of a “child of modest means”: “The child knew only that trains passed over the Van Woert Street trestle and chugged up the Cut to the West, knew railroads had magic all right because in the kitchen there hung a sepia print of a grandfather and two granduncles standing beside Engine 151 on a clear day in the century’s teens.”

Stefan Beck is a contributor to CJR.