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Tammany’s Boss

Monday, August 1, 2005

Kenneth D. Ackerman.
Boss Tweed.
Carroll & Graf. 437 pages. $27.00

Tammany Hall, the popular name of Manhattan’s now-defunct Democratic machine, exerts an enduring fascination on the American imagination. From G.W. Plunkitt of the Very Plain Talks to Carmine de Sapio, the “Last Boss,” Tammany has achieved a sure place in America’s mythology. This appears puzzling at first glance. Why should a citizenry so devoted to republican principles, to the sanctity of the vote, and to the belief that moral and political leadership are very nearly identical be intrigued by any organization that flouted electoral law so openly and with such verve, did its will so fearlessly through bribery and intimidation, and generally made such a mockery of our revered political processes? And one that, moreover, prospered and thrived in spite of its bad behavior, enjoying great popular support and exerting for a time almost imperial power? Don’t we, as a country, value and reward probity, enterprise, and disciplined risk-taking? Don’t we expect to see virtue rewarded and vice punished, preferably in a humiliating and public manner?

Though the lore of Tammany Hall may provide both the vicarious thrills derived from reading of brazen wrongdoing and the satisfying spectacle of thwarted justice eventually taking its course, it seems undeniable that accounts of the Tammany years excite and hold the attention of modern Americans for the same reason that accounts of the reigns of Caligula, Nero, and Elagabalus do: The events they describe are offenses against every political piety that clouds our atmosphere, offenses thoroughly, wickedly enjoyable to read of at our sufficient distance. And no name from those years carries with it more infamy or more excitement than that of William Magear Tweed, Tammany’s most famous boss. Even the image of Tweed that comes reflexively to mind — Thomas Nast’s indelible caricature, a bloated, buzzard-like figure with hooded eyes and a beaked nose — belongs with the likes of Long John Silver and the various other pillagers who enliven the pages of boy’s-adventure books.

Kenneth D. Ackerman, in Boss Tweed, has produced a history not only of Tweed, but of the decades of his greatest prominence and greatest ignominy, a history of his partners in crime and his most implacable enemies. In the midst of all this it is often difficult to discern the figure of Tweed himself and what, if anything, he means or meant to and for America. It is lucky, then, for Ackerman that Tweed and his times hold our interest so effortlessly and lastingly.


William m. tweed commenced life as the much-loved son of a furniture maker. The beginnings of his path to political prominence were fairly common: He began as a volunteer fireman and ward politician in lower Manhattan. He had already been elected chief of Tammany Hall when, in 1863, the Draft Riots plunged Manhattan into social and political turbulence. Through involved and astute political maneuvering, Tweed managed to have Tammany Hall designated as the main administrative apparatus of President Lincoln’s draft in the city. This was Tweed’s first real grab at the kind of power he would later come to wield with such assurance. His masterstroke, at once a public-relations coup and a sound political entrenching tactic, laid the groundwork for Tweed’s next major move: the simultaneous election, in 1868, of Tammany men, his hand-picked slate, to the governorship of the state of New York and the mayoralty of New York City. It is here that Tweed, chief of Tammany and later state senator and commissioner of public works, began in earnest his true career as an eminence grise: dispenser of huge largesse and electoral favors, receiver of equally huge kickbacks from city contractors, plunderer of tax and treasury monies.

He was assisted in this by four cronies: Governor John Hoffman, City Chamberlain Peter Barr Sweeney, Comptroller Daniel Connolly, and Mayor A. Oakey Hall. These are the figures flanking Tweed in the vitriolic stream of political cartoons that issued against him from the pen of Harper’s Weekly’s Thomas Nast. Together, these four put into place the elaborate financial machinery that allowed them to rob New York of more than $120 million (in today’s dollars) by 1870, with more than $20 million of that fattening Tweed’s own purse. As if in perverse proof of Max Weber’s theory of the Protestant ethic, this was the year that Tweed received the public approval of Peter Cooper, one of the pillars of legitimate New York society. And while It is true that in 1871 a few details of the scheme leaked out in the New York Times, these revelations remained largely without effect: “a solid punch, but not more,” in Kenneth Ackerman’s phrase.

But a bloody riot on Orange Day, July 12, 1871, proved to be the crack in the dike. The first real public outcry arose against Tammany in the wake of this riot, and when, ten days later, the New York Times went public with the actual figures, copied from city ledgers, that proved Tweed’s fraud beyond a shadow of a doubt, the blow that had failed to land some months earlier finally struck its mark. By the end of the year, Tweed was a doomed man: He had been arrested and released on bail, resigned his post as the commissioner of public works, and been voted out of his post as chairman of Tammany’s general committee (though he had, miraculously, won re-election to his seat in the state senate while all this was happening).

He was tried and acquitted by hung jury in 1872, but in 1873 he was convicted after a shockingly brief four-day trial presided over by Judge Noah David, a clean-cut upstate Republican. Imprisoned first on Blackwell’s Island, then in the Ludlow Street jail (not far from his old ward), Tweed enjoyed all the benefits proper to a man of his stature — including hiring a fellow inmate to act as his valet. But his story changes here from tragedy to farce: Near the end of 1874, Tweed made an ill-considered escape attempt. He got as far as Spain, where he was arrested for lacking papers and summarily returned to Ludlow Street. Cornered at last, Tweed wrote up a full confession in the hopes of garnering an early release, and the state began its clumsy criminal and civil prosecutions of the other members of his ring. Finally, in 1878, still in prison notwithstanding his efforts to help convict his former cronies, and suffering from diabetes and heart disease, Tweed died, leaving a ruined family, a severely damaged party machine, a city with skyrocketing debt and credit problems, and an ineffaceable mark on American political history.


Given tweed’s energy and ingenuity, not to mention his ability to turn a phrase, his penchant for extravagance, his meteoric rise and abrupt downfall, and the Neronian scale of his corruption, any book on him ought to be welcome. Kenneth Ackerman’s Boss Tweed reads more like a civics textbook than the rich biography it should be. This is not for lack of skill, or of an eye for illuminating detail, or any gap in Ackerman’s knowledge of his subject, or any lapse of taste or psychological obtuseness on his part. If anything, he includes too much, even of the telling and relevant. As a result, possibly, of this ecumenism, Boss Tweed lacks a center. This is a serious flaw in a book that purports to detail the life and adventures of the “corrupt pol who conceived the soul of modern New York” — in the words of the subtitle — and at whose heart we naturally expect to find the man himself.

Tweed’s astonishingly quick ascent within Tammany to the position of chairman of its general committee flashes before the reader’s eyes in three tantalizing paragraphs, and we are left hungering for stories of the backroom deals and political infighting that Tweed must have prosecuted in order to attain the chair. Also conspicuously absent are Tweed’s youth and young manhood, which Ackerman dispatches in a few cursory pages, leaving unanswered a troubling question: How does the cherished son of a respectable middle-class artisan go on to become a political bogeyman like Boss Tweed? How did he develop and hone the instincts that were to carry him so far and eventually ruin him?

This might, indeed, be the most fascinating question raised and left unanswered in Ackerman’s book. Tweed could just as easily have finished as a member of New York’s striving class. He was a child of America’s burgeoning middle class; he had a loving, hardworking father who saw enough talent in him to justify the expense of a year of boarding school; he had a head for figures and, as his later exploits showed, no lack of good business sense. His father was a furniture maker; given Tweed’s proclivities and the unabashedly capitalist taste of the times, it is not hard to imagine Tweed presiding over a booming expansion of his father’s business, and ending his life as a celebrated, harmless merchant prince, an endower of philanthropic institutions, another Peter Cooper.

Why are the stories of men and women who succeed fantastically, aided in no small part by their sheer indifference to and contempt for the mores of business, politics, or social traffic, so enduringly fascinating? To judge from the number of cultural artifacts we have produced that take as their theme the adventures of gunslingers and Mafiosi, one might think that, underneath our dreary republican colors, beat the impassioned hearts of anarchists. Yet this fascination makes perverse sense without even having to imagine some thwarted antinomian impulse on our part: Tweed succeeded in politics and in crime by means of qualities — resolution, intellectual agility, and an eye ruthlessly directed toward the main chance — that would have stood him in excellent stead in almost any approved walk of life, where they would have been chalked up to his entrepreneurial spirit. And though he may have committed great frauds and done near-irreparable economic damage to the city and citizens of New York, his story reminds us of every tale of men of humble origin who ascended to great wealth and power through energy and will, and his fall resembles suspiciously the fall of any other reckless titan of business. Despite his criminality, Tweed’s virtues and vices are uniquely American — or, at least, they play a prominent part in our mythological, self-invented national character. Horatio Alger wrote two novels whose titles, Adrift In New York and The World Before Him, bring to our mind’s eye figures like Tweed far more clearly than the forgettable, industrious moppets who actually grace their pages.

We expect a certain depth of insight — or, at the very least, an illuminating picture of American decadence at the dawn of the Gilded Age — from a book like Ackerman’s, so emphatically titled, so rife with concentrated detail, and so meticulously researched. But despite the book’s close observation of Tweed’s every move, the closest Ackerman comes to offering us such an insight is in his judicious selection of Tweed’s words to serve as epigraphs: We feel closest at these moments to understanding Tweed’s doubtlessly powerful and subtle mind. Yet while Ackerman has obvious talent for vividly animating scenes from history, even incidental ones — Governor Horatio Seymour rushing home from Long Branch to deal with the Draft Riots; Tweed in the course of his crack-brained escape to Spain — he is not able to draw from them much in the way of psychological understanding. This is a particularly serious failure in the case of a subject like Tweed, whose main interest to the reader is as a character in the literary sense of the word.

Still, Ackerman happily touches on  — though it is literally in the book’s last moments — one of the most important aspects of this character: the inextricable connection between Tweed and his city. Where else but in the most ungovernable metropolis yet to have arisen in human history could we hope to find William Magear Tweed? It’s true that, in our sanitized times, men like Tweed and the qualities they embody have come in for a good deal of opprobrium. Is it possible to imagine any public figure more antithetical to Tweed than a purse-lipped, supercilious drinkwater like Eliot Spitzer? And if we criticize the times as decadent and avaricious on the grounds of their having produced men like Tweed, don’t we also have to laud them, on these same points, for producing men like August Belmont, father of the New York subway? Or for the feats — among them the Brooklyn Bridge — of unfathomable knowledge and skill they witnessed? Ackerman concludes his book with the following: “[Tweed’s] swagger is as much a part of modern New York City as the steel, the concrete, the noise, and the traffic. That’s a good enough monument for him.” He is right, of course: The quality he describes, “swagger” (a word evocative also of cowboys and Mafia gunmen), is a defining characteristic of Manhattan even now, both in its reality and in its mythic existence in America’s imagination. It is unfortunate that Ackerman leaves these depths unplumbed. America’s character remains a subject of intense argument in every age, and the more light shed onto the personalities, vicious or virtuous, who have left their mark on that character, the more vivid and illuminating this argument will be.