The Boss, and How He Came to Rule New York by Alfred Henry Lewis

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By Charlotte Girard Posted on Jan 2, 2026
In Category - Adventure
Lewis, Alfred Henry, 1857-1914 Lewis, Alfred Henry, 1857-1914
English
Ever wonder how the political machines of old New York really worked? This book pulls back the curtain on the rise of a fictional boss named Richard B. Croker—though you’ll swear you’ve met his real-life counterparts. It’s not just about backroom deals and cigar smoke; it’s a story about how power is built, one favor, one threat, and one neighborhood at a time. If you like stories about ambition, corruption, and the messy truth behind city politics, this one will grab you. It feels less like a dusty history lesson and more like a guided tour through the city's shadowy corridors.
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whether I hope for good or ill therefrom, I am not able to set forth. There is that within my bosom to urge me to this work, that much I know; the thing uncertain being--is it vanity, or is it remorse or a hunger for sympathy to so ride me and force my frankness to top-speed? There comes one thought: however black that robe of reputation which the truth weaves for me, it will seem milk-white when laid side by side with what Mendacity has invented and Malice sworn to as the story of my career. Before I lift the latch of narration, I would have you pardon me a first defensive word. Conceiving that, in the theory of politics, whatever the practice may discover, there is such a commodity as morals and such a ware as truth, and, remembering how much as the Chief of Tammany Hall I have been condemned by purists and folk voluble for reform as a fashion of City Satan, striving for all that was ebon in local conditions and control, I would remind the reader--hoping his mind to be unbiased and that he will hold fairly the scales for me--that both morals and truth as questions will ever depend for their answer on environment and point of view. The morality of one man is the sin of another, and the truth in this mouth is the serpent lie in that. Having said this much, let me now go forward without more of flourish or time to be eaten up with words. THE BOSS CHAPTER I--HOW THE BOSS CAME TO NEW YORK MY father was a blacksmith, and he and my mother came out of Clonmel, where I myself was born. There were four to our family, for besides my father and mother, I owned a sister named Anne, she being my better in age by a couple of years. Anne is dead now, with all those others I have loved, and under the grass roots; but while she lived--and she did not pass until after I had reached the size and manners of a man--she abode a sort of second mother to me, and the littlest of my interests was her chief concern. That Anne was thus tenderly about my destinies, worked doubtless a deal of fortunate good to me. By nature, while nothing vicious, I was as lawless as a savage; and being resentful of boundaries and as set for liberty as water down hill, I needed her influence to hold me in some quiet order. That I have the least of letters is due wholly to Anne, for school stood to me, child and boy, as hateful as a rainy day, and it was only by her going with me to sit by my side and show me my blurred way across the page that I would mind my book at all. It was upon a day rearward more than fifty years when my father, gathering together our slight belongings, took us aboard ship for America. We were six weeks between Queenstown and New York; the ship my father chose used sails, and there arose unfriendly seas and winds to baffle us and set us back. For myself, I hold no clear memory of that voyage, since I was but seven at the time. Nor could I have been called good company; I wept every foot of the way, being sick from shore to shore, having no more stomach to put to sea with then than I have now. It was eight of the clock on a certain July night that my...

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The Story

This book follows the rise of a man named Richard B. Croker from his early days as a street tough to his reign as the undisputed political boss of New York City. It’s a fictionalized account, but it’s packed with the real grit of Tammany Hall politics. We see how he builds his empire not with grand speeches, but by understanding what people need—a job, protection, help with the law—and making sure he’s the one to provide it. Every handshake is an investment, and every favor is a chain. The story shows the slow, deliberate construction of a system where loyalty is the only currency that matters.

Why You Should Read It

What struck me was how familiar it all feels. The mechanisms of power Lewis describes—patronage, controlling nominations, rewarding friends—aren’t locked in the past. You can see their echoes today. Croker is a fascinating character because he’s not a cartoon villain. He’s shrewd, pragmatic, and understands the city’s heartbeat better than any reformer. The book doesn’t just judge him; it shows you exactly how and why his world works. It’s a masterclass in practical politics, for better and much worse.

Final Verdict

Perfect for anyone who loves political dramas like Boss Tweed or The Power Broker. It’s also a great pick if you enjoy character-driven stories about ambition and the price of power. The writing is straightforward and pulls you right into the smoky rooms and crowded streets. Just be prepared: after reading this, you’ll look at every local election a little differently.



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