In the early 1990s, when he was running for office and losing just about every year, John O’Hara was known as “Mad Dog” for his quixotic campaigns. Appropriately, his political enemies wanted the young lawyer “leashed, muzzled, and caged, if not shot,” as one of them put it to me. Such was the notoriously vindictive — some would say corrupt — atmosphere of Democratic machine politics in Brooklyn. In the old days, insurgents got their legs broken by plug-uglies, or lost ferociously at the polls by the hands of repeaters. Today, the world being less simple, you go before a winking judge to get thrown off the ballot on a technicality and end up bankrupted from the court costs. The plug-uglies have law degrees.

In O’Hara’s case, he was also charged with a felony for the impudence of his candidacies. He was heavily fined and, in lieu of prison, given five years’ probation and fifteen hundred hours of community service, which consisted of cleaning up garbage in parks. I got to know O’Hara drinking in seedy old bars late at night. One day in 2003, I went to see him working off his garbage detail. The martyrdom of the labor seemed to please him — O’Hara envisioned himself a “political prisoner” — and for that reason he enjoyed visitors. It was April and sunny and strangely hot, and O’Hara was crouched in the grass beer-bellied and sweating as he gathered trash into big black bags. “The chain gang!” he snorted when I walked up. Then he exploded in laughter. Here he was, a felon since 1997, stripped of his law license and his livelihood (he had been a Wall Street attorney), the son of working-class Irish, the first in his family to go to college, and now his supervisor was directing him to swab the feces from the park’s toilets. “Long way from Wall Street,” he said, talking, as usual, out of the side of his mouth in a kind of half-baked James Cagney. Then he burst again into his red-faced, big-shouldered laugh.

The mirth arose, in part, because the corruption that had rendered O’Hara a footnote was now, in April of 2003, exploding across the front pages of New York’s dailies. Most of it centered on the Brooklyn courthouse where O’Hara had been, as he described it, “fucked in the ass by a hack judge.” There were charges of bribery and case-fixing, of judges paying as much as $100,000 to climb the bench, of extortion by Democratic Party bosses. One judge was caught soliciting $115,000 to fix a personal-injury suit. In the surrogate’s court an estimated $8 million had disappeared from Brooklyn estates into the pockets of the party’s crony lawyers. It was an embarrassing year for the borough, a throwback to the old Tammany rottenness, or, rather, evidence that Tammany had never really gone away. To top it off, that summer a Brooklyn councilman was assassinated at gunpoint by a psychotic rival, who himself was shot down in the act. The assassin was an insurgent who had been forced off the ballot one too many times and, apparently, been driv-en nuts by the system. He became a terrorist — the other path O’Hara sometimes pondered after too many beers.

But O’Hara believed too much in the lessons of his civics teachers; he believed in the system as the Founders established it: pluralistic, agonistic, a cacophony of voices, not guns. He wanted to run for office; the machine did what it had to do. Still, if one worked hard enough, the machine could be fought and conquered and eventually dismantled, or so O’Hara believed. Watching him clean toilets, I began to think that here was what happened when a person, alone, tried to shake up a dying democracy. In retrospect, this was naive. I had grown up in Brooklyn, lived in Brooklyn my whole life, never knowing that the machine was all around me — that perhaps Brooklyn was not a failure of democracy but the fate of democracy; not the anachronism but the model, and the future, even, of the nation.

Brooklyn, of course, is a degenerated branch of an old species, big-city bossism, that once covered the American landscape. William Marcy Tweed, porcine inventor of machine politics and archetype of the boss, planted the form into the urban soil in the 1860s. It fed on the peculiar nexus of mass immigration and municipal expansion that arguably defined American life in the half century after the Civil War. Immigrants packed the hostile cities, bereft and beaten-up, and the bosses, often their countrymen (Irish, immigrant, working class), met them with the offer of a simple graft that was the essential component of all machines. The newcomer was quickly naturalized and registered to vote and was given a job or shelter, or, later, turkeys at Easter or hods of coal in winter. The boss, in return, got the vote of a desperately thankful man, a vote that was obedient and reliable. The boss purchased the votes of the neediest with the same aplomb that he sold off city contracts to the greediest. This was no new phenomenon: politics as business, the politician as power broker. But before the advent of the boss, American politicians were understood, conceptually, as gentry, a disinterested class of the educated “best men.” Now the politico rose from the tenement.

By 1890, half of America’s twenty largest municipalities were run by machines, and the other half were heading that way. Some, like Tammany under Tweed, stretched their power into the legislatures; some “made” presidents. Most were Democratic, like Boston and Kansas City and San Francisco; a few were Republican, such as Philadelphia and Pittsburgh; and some, like Albany, regularly switched camps. All at one time or another were fantastically corrupt, profiteering on the staggering urban growth of the Gilded Age (New York’s Tenth Ward, on the Lower East Side, was calculated in the 1890s to be the densest human habitation on earth). Bonds, rent, tax assessments, utilities, docks, streets, sewers, public transit — everything was for sale. In New York, the Tweed courthouse eventually cost four times the Houses of Parliament. A Tweed contractor charged $2,870,464.06 for a plastering job that should have cost $20,000. Padding every account, the Tweed Ring in a mere decade bilked taxpayers of at least $100 million (more than $1.3 billion in today’s money). In Philadelphia, “the city of Brotherly Loot,” grafters joked that they counted the take to the chimes of Independence Hall. Courts were stacked, elections stolen. In New York, Hell-Cat Maggie, a “shoulder-hitter,” filed her front teeth and wore brass claws on her fingers as she tore into Republicans on Election Day. The brutality reached a high point of sorts in March 1934, when the Tom Pendergast machine in Kansas City (which pushed Truman into national politics) murdered four people and assaulted more than 200 more to secure a plurality of 59,000 votes. “The spirit of graft and of lawlessness is the American spirit,” lamented Lincoln Steffens, the muckraker, in a moment of tragic pique. In Minneapolis, he reported in 1904, “thieves and swindlers” had even been invited “to go to work” by the police department: “The government of a city asked criminals to rob the people.”

Steffens was journalism’s answer to the new politics — he was one of the first investigative reporters — and he tabulated for history, in the collection of magazine pieces that he called “The Shame of the Cities,” the price of the machines’ widening greed. In bossism and bribery and corruption Steffens saw “no ordinary felony, but treason” against the hopes of the republic. “The effect of it,” he wrote, “is literally to change the form of our government from one that is representative of the people to an oligarchy.” As for the vaunted boss, he was “the product of a freed people that have not the spirit to be free.” Steffens soon found, to his dismay, that the outcry made no appreciable difference in the public mind. The people were not ashamed, so long as they got theirs.

Steffens died just shy of the reforms of the 1940s that undercut the machines after almost a century of sway. Civil-service merit testing, non-partisan elections, the secret ballot, and the rise of the welfare state stripped the bosses of purpose and resources — the federal handout usurped the ward handout — and by the end of the New Deal era, the big-city machines had disappeared or had been balkanized into county operations. The holdouts in New York City — the Bronx, Queens, and Brooklyn machines — pivoted and adapted, consolidating federal and state entitlements into the “honest graft” of patronage for a rising middle class, with blacks and Hispanics now the recipients of the handout that once drew the Irish vote. This was the model of the Daley machine in Chicago (and persists today under Richard Daley Jr.), as it was also the model, tweaked to fit the suburban homeowner, in Nassau County on Long Island, where, as recently as the 1980s, a Republican machine controlled 20,000 jobs. The objective was always the same: monopolization of public money, the starvation of opponents, a total dominion of the ballot box through favor — honest graft that Brooklyn by the 1970s, when John O’Hara was running his first petitions, had raised to the level of art.

At the age of seven, John O’Hara was writing letters to his congressman, complaining that he paid sales tax on toys but didn’t have the right to vote. Four years later, he worked his first campaign, McGovern for president, handing out flyers, and was devastated when McGovern lost in a landslide. By the age of sixteen, he was investigating malfeasance for the high school newspaper and caused a minor storm when he got the school principal fired for not having a principal’s license. The story made the Daily News.

To O’Hara, muckraking and reform — cleaning up Brooklyn, changing the world — were the only legitimate reasons to get into politics. The reform movement of 1974 gave him the chance. The boss of Brooklyn then was the legendary Meade Esposito, who, like the bosses before him, became rich fleecing the system. Like them, he was fat, jolly, profane, mob-connected, vengeful as an emperor, kind to his neighborhood, and frank about his larceny. Like them, he was at one point “boss of the fucking state,” as he himself said; Governor Nelson Rockefeller sent him a Picasso for his favors. “Don’t say I was honest,” Esposito told reporters, “just say I never got caught.”

His preferred medium of graft was the justice system itself, the lawyers and the made judges who gave the lawyers business or found favorably in their cases. It was also the local newspapers that advertised courthouse auctions. It was the landlords and developers who contributed to the party and got the zoning or tax breaks they wanted; the printers who got the palm card and petition contracts; the civil-service unions whose “merit” employment was rarely enforced. No-bid, backroom dealing sealed these relationships, all of them vaguely legal and perfectly corrupt.

The 1974 reform that hoped to clean all this up was, like most municipal revolts, messianic, middle class, sincere, and righteous. It rose out of the run-down Irish enclave of row houses and walk-ups of central Brooklyn, the neighborhoods of Park Slope and Sunset Park, where O’Hara grew up. The rebels met in an old smoky storefront that had three folding chairs, a folding table, and one phone; they traveled in a rusty van, throwing buttons from a big white bag while people threw eggs at their heads. They ran candidates for district leader, state senate, state assembly, and for governor they backed Sunset Park’s congressman, Hugh Carey, whom Esposito strongly opposed. The slate swept to victory; O’Hara got his first taste of drunkenness in celebration.

By the 1980s, however, the movement had dwindled to a few recognizable figures, chief among them a Yale graduate and Manhattan lawyer named Jim Brennan, who, as the state assemblyman from Park Slope, would become known for his integrity and shrewdness. And yet, as so often happens, Brennan’s reform soon became a machine of its own. This wasn’t in keeping with the world-shattering revolt young O’Hara had envisioned, and in its own way was an even more threatening repudiation of everything O’Hara had hoped for.

A machine exists to produce money for the people who operate it, yes, but what a machine does in fact is even simpler: it wins elections, and it wins them repeatedly, by whatever means. By definition, then, a machine is a creature of democracy, arising only where universal franchise and electoral competition meet and particularly where rapid urbanization couples with rising need and a systemic failure to meet the need — where social change threatens a descent into chaos and collapse.¹ This was the challenge that the American machines met and conquered at the end of the nineteenth century, and it can be argued that machine governance, under the masterful guidance of the boss, forged the modern American city.

Facing a gigantically fragmented field of ethnicities and parochial interests, the bosses saw with no little prescience that eighteenth-century charters written for the village and the town could no longer juggle the conflicts of a metropolis. Only by what one Tweed biographer called the “big pay-off” — mass corruption — could he mollify all parties to draw them to a common effort. Democracy, in short, demanded graft. And so there was built a shadow government, extra-legal but functional, and that was the key: pragmatic, opportunistic, flexible, the bosses got things done. Even Lincoln Steffens in his moral fervor recognized the complexity of the solution to the problem of the city that the bosses represented. Martin Lomasney of Boston was perhaps the most eloquent in explaining bossism to the young reporter: “There’s got to be in every ward somebody that any bloke can come to — no matter what he’s done — and get help. Help, you understand; none of your law and justice, but help.” The bosses, with their wards and clubhouses, saloon meetings and torchlight parades and street parties, humanized politics; they gave the underdog a chance at survival. (Explicit losers in a Protestant world, the Irish turned to the machine; the Italians, traveling the same shadow road, turned to the mob. Thus were the two peoples stirred into the melting pot.²) Daniel Patrick Moynihan wrote that the machines were the first example in history of sustained governance of a city “by men of the people,” though perhaps one could find antecedents in the reign of the Gracchi in Rome or the Commune in Paris. Models of upward mobility, the bosses created a welfare state before there was such a thing, before government was equipped, or cared, to deal with the ills of the typhus ward and the suicide ward, with its epidemics of crime, alcoholism, hopelessness. Unlike the bureaucrats who replaced him, the boss answered need with no questions, no “damn fool investigations,” as Tom Pendergast explained. “No, by God, we fill his belly and warm his back and vote him our way.”
The boss’s ultimate goal, however, was order, not progress, so he was violently anti-labor, crushing radicalism wherever it appeared, and never sought to institutionalize his services. And yet, paradoxically, the boss embraced a kind of progressivism, if only because bettering the city bought him votes, kept him in power, and filled his pockets. Brokering huge franchises and monopolies, he improved roads, sewers, lighting, built libraries and parks and museums and hospitals, extended subways and trolleys and docks. Tammany at its height produced the Brooklyn Bridge and the Museum of Natural History.

But the secret labor of the machine, as one historian wrote, was “to watch over and manage the disappearance of real power from public view,” the end of which was a kind of soft despotism. Controlling the courts, the police, the legislature, the ballot box, and the nominating conventions, and abetted in all this by the wealthiest elites, machine bosses drove the people into the agora merely to receive the imprimatur that continued rule required. Love and fear were the goads, not the ideal of self-government. “The American citizen does not understand self- or representative government, and does not demand it,” wrote Steffens in an open letter to Czar Nicholas II. “The American people are asking for ‘good government.’ All they mean by this is clean streets, well lighted and honestly policed by a police force which, if it must blackmail vice and protect crime, shall do so quietly.” Steffens assured the czar that even under the bother of the franchise and a constitution, Russia’s autocracy might continue unmolested.

By 1984, at the age of twenty-three, O’Hara had made bitter enemies of just about every one of his mentors in the Brooklyn reform movement. Naturally, they had handed out patronage, stacked legislative committees, created “no-show” and “seldom-show” jobs (as the New York Times observed). The reform machine under Brennan followed the same ethos as every machine: loyalty was sainthood; betrayal, apostasy. This was an Irish ethos. O’Hara’s defection was also an Irish habit, the periodic rebellion against the crown that usually ended badly for the rebel. O’Hara wanted “purity,” a cleansing of the municipal ground, the same “self-government” Steffens sought but didn’t know how to deliver. And purity was a state achieved only by never getting elected.

Still, O’Hara the maverick set out to reform the reformers. In 1990 he finally passed the New York bar; it was his sixth try. He’d paid for CUNY law school by driving taxis on the night shift; he kept a poster from the movie Taxi Driver on his wall. In the 1990s he ran for office against Brennan or Brennan’s cronies six times in almost as many years, for state assembly and for city council. In 1992, at age thirty-one, he lost against Brennan’s handpicked candidate by just a few hundred votes. He was emboldened. He became known across Brooklyn as “the gadfly,” the “perennial candidate.” The Times called him a “political brawler.” The Brennanites never tired of painting O’Hara as a criminal for this enthusiasm. Brennan denounced him to the public as a “psychopath,” and legends arose that O’Hara’s mayhem was not limited to electoral challenge. The allegations were always unproven, and there was never a police report or complaint or investigation, but the legends, repeated enough, stuck, and among the Brennanites they became a kind of contagious delusion. There was the vision of a crazed O’Hara swinging a bat in front of a Brennan crony’s house; there was O’Hara dressed in a clown suit terrorizing Jim Brennan’s neighbors. O’Hara could be crude and growling and arrogant — a friend once called him “King of the Ballbusters” — and when he thought you disagreed with him he pushed and cajoled and poked you on the shoulder and asked, “Whattaya, got two sticks rubbing together for a brain? Of course I’m right!” His mouth once landed him in a wheelchair in the emergency room. But his ball-busting, it seemed to me, was simple Brooklyn frankness, not pathology. Indeed, the lack of artifice reminded me most of the old Tammany bosses.

In any case, his public record spoke louder than the rumors of blood. The Citizens Union, New York’s oldest good-government group, concluded that O’Hara was “a man of considerable charm” and “an outstanding civic activist in his home district.” In 1992 the Times endorsed him for state assembly among five contenders, praising his “feel for the district.” Joyce Purnick, who wrote the endorsement, told me the editorial board “felt O’Hara would shake things up a bit in Albany.”

His campaign head-quarters was over a cop bar where the drunks, off-duty, discharged their pistols into the ceiling for kicks. He ran his campaigns on pennies, raising money “on the streets,” trawling the lower reaches of Broadway, among the law firms of the financial district. He did well with old-timers, though, who grew up poor in Brooklyn and had made a name for themselves and moved out to mansions on Long Island — “old Jewish guys, old hustlers, they had it tough, they got where they were ’cause they had balls.” An executive once gave O’Hara $1,500 after he’d elbowed his way into the office, sat down, and told him his vision of state government. “Blow it up. Burn it to the ground,” O’Hara said. “Real reform means the system as it stands has to be annihilated, because right now it’s failing by design. Millions of dollars are wasted every time the legislature fails to pass the budget. And that’s the only thing it does consistently.³ What I’d like to do is get a popular referendum to abolish the legislature and start over. You never see politicians getting laid off. I say lay ’em all off!”

“Okay, you seem like you’re into it,” the executive said, wishing he hadn’t let O’Hara in. But he gave him the money.

Boss Tweed near the height of his plundering was cornered by reporters and accused of defrauding the public. “What are you going to do about it?” he said. Lincoln Steffens called this “the most humiliating challenge ever issued by the One Man to the Many,” which was arguable, but it colored everything that urban scholars later wrote about civic reform. Steffens was characteristically gloomy about what, exactly, would be done: “Reform with us,” he observed, “is usually revolt, not government, and is soon over.” In 1871 a reform revolt toppled the boss of bosses from power; similar spasms toppled his Tammany heirs four times between 1894 and 1933. Yet Tammany always emerged stronger, better managed, because nothing much seemed to get done under reform administrations. Tweed and the boss crowd were portrayed as frothing monkeys and birds of prey, but the worst of the reformers were effete, priggish, Protestant, patrician, reaching backward to an edenic state of governance — pre-immigrant, Yankee-pure — that probably never existed and could not exist. The bosses called them “Goo-Goos,” “YMCA types,” “silk hats and silk socks and nothing in between.” The masses wanted tangibles; the reformers gave them ideology. The reformers often were more interested in legislating morality — shutting saloons, jailing prostitutes — than in improving conditions, though the message was couched in high concern. Put “good men” in place of the monkeys and vultures, the theory went, and presto, you’d have a new age in governance. Sincerity, of course, did not translate to intelligent action.

Still, cycles of reform and reaction were as regular as the seasons, a law of political life. Nationally, the Populist Party, born in 1892 of agrarian unrest, decried the “vast conspiracy against mankind” represented by “capitalists, corporations, national banks, rings, trusts,” and the “millionaire’s club” that was the U.S. Senate in the Gilded Age (and still is). The “people’s party” demanded fair wages, government ownership of utilities, corporate regulation — the first national progressive platform. Four years later, the people got William McKinley, the robber baron’s president. McKinley’s manager, the Ohio senator and boss Mark Hanna, pioneered the modern campaign of the mass corporate shakedown, raising an unprecedented $7 million (some $150 million today). En revanche, there was Theodore Roosevelt, whose “Square Deal” balanced business and regulation, and, as a result, set the federal government on course to its modern shape.

Roosevelt’s playbook in this uphill fight was written in the cities, where by 1900 the most effective reformers, not surprisingly, had harnessed bossism to the cause. The so-called reform bosses, notably in Cleveland and Detroit, used the powers of the machine to regulate or purchase outright the franchises and utilities and public transit that had produced such lucrative graft. They established unemployment relief, workplace safety, the eight-hour day, fair taxation. The convictions embodied in the Square Deal, the New Deal, Truman’s Fair Deal, the Great Society — the structures that made the bosses irrelevant — were all born, to some degree, out of the Democratic rank-and-file of the urban machines. The reform bosses had reformed themselves out of existence.

The reform machine in Brooklyn made no such error, positing itself as the honest alternative to the “regular” machine that chugged on even after Meade Esposito died in 1993 (eighty-six years old and $6 million richer). The reformers thrived as a result — won elections, got posts, drew state money — but to an outsider they looked more like a toothless minority party that, true to reform’s finest tradition, never got much done.

Such was the relative value of honesty. As for John O’Hara, he had a premium on the stuff; by the mid-1990s he was considered a failure in politics, a perennial loser. His base, the elderly Irish and Italians of Sunset Park, had died off or evaporated to the suburbs, replaced by Hispanic power that the reform machine had channeled to its own ends.

Somehow, though, he managed to get on the ballot year after year. In the demented labyrinths of New York state election law, this can amount to an epic act, for New York allows nominating petitions to be challenged by one’s opponent on the most picayune grounds (a bungled address, a typo, an unsigned cover sheet). Each year, vast sums are spent on eagle-eyed election lawyers, who at $400 an hour invalidate one by one the signatures on the green sheets, nullifying entire candidacies under the pall of court-clogging “petition fraud” lawsuits. The result of this often inane rite is that the state of New York for years produced over 50 percent of all election litigation in the United States. Ironically, these traps and pitfalls, designed to prevent the wholesale election frauds perfected by the old machine, are now the chief machine weapon to quell insurgency.

In election year 1996, the year of his arrest, John O’Hara had fought from under a particularly long and brutal petition challenge by Jim Brennan. He was also under investigation by the Brooklyn district attorney. Men from the D.A.’s office had shown up at his mother’s house, banging on the door, asking for her, for him, but his mother was too frightened to answer. The detectives visited his campaign headquarters and his apartment, where they’d rifled his garbage, tossing it in the street. O’Hara kept on the move, staying with friends, living on couches, convinced that his phone was tapped.

The election itself, on September 10, was “the worst electoral debacle in modern city history,” according to the Village Voice. By midday, polling places had collapsed into chaos, following the late arrival of some 1,700 voting booths that were expected to be delivered overnight from the city Board of Elections. Crowds of angry voters queued in the unseasonable heat and were finally sent home, and investigators later concluded that at least 10,000 Brooklynites, and possibly many more, were disenfranchised, victims of an internecine war over control of the patronage-rich surrogate’s court. Fittingly, a local newspaper soon ran a cartoon showing U.N. blue helmets marching into Brooklyn with guns drawn.

O’Hara’s own paranoia proved prescient that day as well, when his girlfriend was attacked on the street as she handed out flyers for his campaign. Court records identified the assailant as John Keefe, the chief of staff to Assemblyman Brennan. According to O’Hara’s girlfriend, it was Brennan himself who piloted the car in which Keefe fled after tearing up her posters and knocking her to the ground. Brennan would not talk to me about this incident, nor would Keefe. Standing amid the police officers and flashing lights and watching his weeping girlfriend give a statement, O’Hara for a brief moment wanted to get in a car and find Brennan and his maniac staffer. But that wasn’t his way. The courts, he vowed, would settle things.

Keefe was soon the beneficiary of an oddly lax justice, courtesy of the Brooklyn district attorney. Indeed, charged with assault and sex abuse in the third degree, Keefe failed to appear at the many hearings, in contravention of basic procedure (criminal defendants are normally always required to appear in person). After a year of adjournments, the main witness for the girlfriend moved to Florida, Keefe copped to a minor harassment plea, and the D.A.’s assistants would not be further distracted. They were apparently busy on a more pressing matter.

Six weeks after the events of September 10, John O’Hara received word from the Brooklyn D.A. that he was a wanted man, for charges unknown. O’Hara surrendered in a kind of fugue shock, riding the subway to the Court Street station, to the D.A.’s office tower, where an aide brought him to a room of peeling plaster and sat him down and handed him the indictment, which told an odd story. From October 1992 to October 1993, O’Hara lived in two apartments in Brooklyn; O’Hara had registered to vote from the second of these two apartments. This second apartment, unfortunately, appeared not to fit the parameters of what the law defines as a “fixed permanent and principal home.” In the ridiculous language of New York state election law, a “fixed” home derives its legitimacy by being the place “to which [the voter] wherever temporarily located always intends to return.” In essence, the law states that a citizen with no fixed location — say, someone living in a hotel, or a transient in a shelter, or studying in a dormitory, or someone with two homes (since only one of these can be “principal and permanent”) — forfeits the right to vote. Like much of New York state election law, the statute is absurd and imbecilic, and has long been determined unconstitutional under federal law. For this reason, no one in the annals of the state had ever been successfully prosecuted under its rubric — until People v. O’Hara. (Incidentally, John O’Hara is the only New Yorker to be convicted of illegal voting since 1873, when suffragette Susan B. Anthony was tried and convicted.) And if voting was the crime, O’Hara was a model recidivist. He had voted in every election for which he was eligible from age eighteen on — scores of ballots over a lifetime. But now a detective fingerprinted him with a worn-out ink pad, flashbulbed him for a mug shot, cuffed him, and took him to a holding cell. The prisoners, three black men, laughed when they heard the charge, and someone muttered, “Glad I don’t vote.”
Thus began a legal odyssey that has lasted eight years. The case originated in the office of O’Hara’s nemesis, Brennan. It was pursued as a favor and then as part of an ultimate calculus by another Irishman, Brooklyn District Attorney Charles “Joe” Hynes, who today remains a pure creature of the Brooklyn machine. D.A. Hynes would regret having ever touched it; he himself turned out to be guilty of almost the very same crime, having once registered to vote from his Brooklyn office (most certainly not a legitimate residence, since he never lived at the location).⁴ Hynes expected O’Hara to plead out to a misdemeanor. But O’Hara was belligerent, and when the case went to trial O’Hara openly mocked his prosecutor. The judge offered him a second plea deal, a variant of a no contest, but this, again, meant standing down, admitting guilt. “Fuck that,” O’Hara said. When he was finally convicted in July of 1999, after a mistrial and a reversal on appeal, the court in its ire fined him $20,000, gave him probation, and told him to clean the borough’s garbage. Certain of vindication, O’Hara appealed the decision a total of ten times, through three state courts and two U.S. appellates, until at last the U.S. Supreme Court, in January 2004, declined to hear his motion to dismiss.

Since the election of George W. Bush, a G.O.P. machine has arisen that, in the intricacy and efficiency of its parts and in the scope of its ambition, would evoke the envy of even Tweed himself. If Brooklyn is the final perfect expression of machine politics at the local level, the national Republican Party seems to have taken corruption to another, more perfect place, for it has managed at last to disconnect the machine from the democracy. No longer need there be a trade-off between the desirable suspension of justice and law and the expansive fact of helping constituents. Tweed would nod knowingly at the corruption and waste of Iraqi reconstruction contracts, the commissioning of the regulatory function to industry lobbyists, the spoils dispensed among Bush’s Pioneers following the victory of 2000. But he would be awed by the concomitant destruction of federal programs designed to help working people. Bossism, in a sense, has come full circle. The G.O.P. machine seeks the destruction of the very welfare state that the old municipal bosses jerry-built for the masses who delivered the vote.

As with the old bosses, though, permanent reign is the overarching purpose, and it is no surprise that the architect and enabler of this venture, Karl Rove, should envision himself as the Mark Hanna of our time. After all, Hanna’s big-money win of 1896 ushered in a thirty-six-year period of six Republican presidencies (interrupted only by the Wilsonian interregnum). Rove’s point man in Congress is House Majority Leader Tom DeLay, enforcer in an unprecedented power grab that seeks, as the key to success, to pauperize and disenfranchise the Democratic Party and render it a permanent minority. DeLay appears to understand that if all politics is machine politics, then the game will be won or lost on a field far removed from either ideology or ethics.

On K Street, for example, Republicans under DeLay increasingly pressure the trade associations and lobbyists to hire only party stalwarts. As an arm of the so-called K Street Project, launched in 1995 in collusion with longtime anti-tax crank Grover Norquist, this effort is catalyzing a major shift in fund-raising, as industry recognizes the obvious advantage of one-party government.

DeLay has also attempted to orchestrate historic mid-decade redistricting in state legislatures, snatching new congressional seats in Texas and attempting to do the same in Colorado and Ohio, shattering the long-standing bipartisan agreement of decennial remapping. Tort reform will neutralize the Democrats’ trial lawyers (as it enriches insurance firms); a fulsome embrace of Israel siphons Jewish money. Privatize Medicare, give the ill health of the nation as spoils to Republican friends and donors. Privatize Social Security, collect on the hundreds of trillions of dollars annually that mutual funds make managing the accounts.

All very honest machinations, and all aimed, as Grover Norquist explains, at realizing the radical right-wing project of reducing the federal government to the size at which government, like an infant in the hands of a mad mother, can “be drowned in a bathtub.” That the government continues to grow at a record rate proves only that ideology is not the friend of the machinist.

It appears that the one pressure this new machine will likely not face is sustained suffrage. In 2002, 98 percent of those seeking reelection to the House of Representatives won, which beats the Politburo for stability. Redistricting ensures this, in tandem with a lax electorate. Fewer than one fifth of eligible Americans vote in primaries, little more than half in presidential elections. (The United States ranks 139th worldwide in national voter turnout since 1945.) Business PAC money goes twenty to one into the incumbent’s pocket. The old machines at least faced the voters with something in their hands, dealing the goods appropriately — spreading the wealth. The new Republican machine has no such need or interest; it benefits only itself, and as such, it is perhaps the purest of machines.

Broke, jobless, drinking too much, John O’Hara opened a copy of the Daily News on April 18, 2001, and saw a story about a poker-faced forty-six-year-old civil-rights lawyer named Sandra Roper, who had been fighting predatory lenders in Brooklyn and once worked for the NAACP; the plates on her purple Chrysler said ms law 1. O’Hara telephoned Roper that evening and was at her storefront office an hour later, pitching a novel concept: he wanted to run her for district attorney of Brooklyn, against the man who had prosecuted him.

“I didn’t know this guy from Adam,” Roper told me. “Then he starts telling me about his arrest. ‘I am a felon,’ he says. ‘Just want to clear that up.’” Roper was gracious and shook his hand, and when he walked out the door, she turned to her associates and said, “Is this guy nuts or what?” Then she booted up her computer, dialed the Internet, and read his story, which struck a nerve. “I was born in Panama, under dictatorship,” Roper told me. “There was a time in that country when you could be at breakfast with your family and by dinnertime they’d been disappeared and were never coming back.” The machine had tried to disappear O’Hara. Roper didn’t like that.

O’Hara wanted to widen the ticket: Roper for D.A., plus at least one other black insurgent to weaken control of the locked judiciary, in which judges serve for decades unopposed. Together, the D.A. and the courts were the keys to power: the former controlled who went to trial and, more importantly, who didn’t; a judge bought was justice compromised. Sandra Roper put out the call to her colleagues to join the ticket, but, fearing disbarment or worse, all of them declined. Desperate, John O’Hara appealed instead for the help of two outsiders who knew nothing about politics, who, like Roper, had never run for office and didn’t know what they had to fear. Eileen Nadelson had been a schoolteacher, an entrepreneur, a journalist, had gone to law school at age forty, and at sixty-two was the long-time president of the New York League of Women Voters, which in 2001 filed an amicus brief in O’Hara’s defense. That brief was written by a pot-bellied, bespectacled trial lawyer named Peter Sweeney, O’Hara’s second judicial pick, who was a chef before he took up the law.

There wasn’t a single paid operative on the Roper campaign. It felt, O’Hara thought, like his youth — like the race that got him into politics, George McGovern’s doomed run of ’72 — except now the foot soldiers were black and Latino, old ladies in senior centers and new immigrants from violent regimes in Haiti, the Dominican Republic, Central America: the future of the Brooklyn vote. Two hundred people petitioned for five weeks and got 12,839 signatures. In late July, Roper filed the big bound petition tomes at seven minutes to midnight on the day of the close of the petition season, arriving at the city Board of Elections in Manhattan in a caravan of ten vehicles packed with her followers, who hooted and cheered. Two blocks away, John O’Hara drank dollar drafts in a foul-smelling bar called the Blarney Stone.

The petitions were immediately challenged in court, and, as it unfolded over a month of vitriol and wrangling, the Roper trial was said to be the largest election-law matter in county history, with more than 10,000 signatures scrutinized. Anyone who had participated was brought in for questioning. There was a heat wave those long weeks, and the courtroom took on the hothouse rock-concert climate that breeds bad nerves and nausea: 300 people corralled, fifteen hours a day, past midnight, in a space not meant for a hundred. “These were ninety-two-year-old ladies brought in,” Sandra Roper told me. “Treated like criminals. This was my neighbor across the street who was dying of cancer. They served my mother with a subpoena, and they served my father, who has been dead since 1989.” Later, Roper was approached in a courthouse bathroom by a well-dressed woman, a stranger, who smiled and said, “Hear they’re gonna disbar you, Sandra.” Roper looked her in the eyes and said nothing.

The judge, Lewis Douglass, seemed to favor the prosecution, which was natural; Douglass was a heavy cash contributor to the Brooklyn Dem-ocratic Party. Peter Sweeney, who led the defense, told me that “Douglass’s attitude was, ‘Don’t say anything that’ll change my mind.’ Then we started cross-examining and scoring points and everyone’s throwing their fists in the air. I wasn’t even an election lawyer — I was flying blind. And I looked over at this wall of lawyers — ten of them — and for each of the lawyers, there were ten more people in the crowd from the D.A.’s office. They put everything they had into that case.”

The month-long marathon ended on a Friday afternoon in late August, and Douglass’s decision came out an hour later; of course he had ruled against the Roper slate. Now O’Hara and Sweeney had two days, the weekend, to summarize the monster of a transcript — 1,600 pages, which cost $8,000 to purchase — and defend their ticket. They sweated like pigs, slept not at all, got so tired they were hearing voices. At 5:00 a.m. on Monday morning, they were at Kinko’s binding briefs, each a hundred pages long, to be filed with the four justices of the New York State Appellate Division, who took three hours to come to a decision, the longest three hours of John O’Hara’s life. Douglass had named him as the source and linchpin of the Roper “frauds,” and as such O’Hara had committed a crime, violating his probation. If the appellate affirmed the Douglass court, O’Hara would have to be re-sentenced, and all expectations pointed to prison. In the most visceral sense, the life of the Roper campaign had become his own. O’Hara heard the news as he stood outside Sweeney’s office in lower Manhattan; Sweeney walked out with his jacket off and shoulders slumped and with a sudden smile said, “Unanimous decision — case reversed. We won.” The two big-bellied men yelled and jumped up and down in circles, “like twelve-year-old girls.”

The celebration did not last long. When the votes were finally counted in late September, Roper lost the 2001 race for D.A., but for Hynes it was a classically Pyrrhic victory. An unknown, unfunded female had taken 37 percent of the vote, and voters don’t trust women as prosecutors. The take-home message was that close to half the electorate would choose anybody other than Joe Hynes. Like O’Hara, Roper is being punished for her audacity. In June 2003 she was indicted in Brooklyn Supreme Court on what most observers agree is an unfounded charge of grand larceny. If convicted, she faces twelve years in prison. John O’Hara felt like it was his fault; he begged her forgiveness. “Hey,” she said, “they warned me.”

Vastly more important — though at the time few predicted it, least of all John O’Hara — was the impact of the Roper race on the shape of the Brooklyn judiciary, for Peter Sweeney and Eileen Nadelson had captured their judgeships against overwhelming odds (Sweeney by less than one half of a percent). Their collective victory was a seismic event. No one in living memory could testify to the last time a countywide judgeship had been won outside the ranks of the Democratic regular machine (and certainly no one in the reform machine had ever really tried). A year later, in 2002, a second wave of judicial insurgents swept Brooklyn; the O’Hara rebellion had raised the suggestion of vulnerability. By 2003 people were openly questioning the pay-to-play scam in the judiciary, the selling of judgeships that lay at the heart of the machine since the days of Meade Esposito. The noise wasn’t the result of sudden ethical enlightenment but a rude calculation of interests. When prospective judges paid their tithe of $50,000 and $100,000, and the machine failed to deliver, they wondered what exactly they were paying for. Then the question became, Why pay at all? One observer told me, “When you factor over time the patronage lost with each lost judgeship” — the law secretaries, the fees to consultants and attorneys — “John O’Hara cost the machine millions of dollars.”

John O’Hara is still picking up garbage and looking for the loophole that will unravel his conviction.⁵ Legal scholars believe that People v. O’Hara, as affirmed in the highest courts, sets a dangerous precedent: New Yorkers now can be prosecuted as criminals for wrongly registering to vote. O’Hara still has no job; his girlfriend supports him; he hopes to be a lawyer again. Jim Brennan is in his twentieth year as a state assemblyman, plodding on with good intentions. John O’Hara has left him behind; he wants to take over the D.A.’s office. We drink in a crappy little bar. He counts the days and hours to 2005, when Joe Hynes is up for reelection. Sandra Roper, he predicts, will beat her case and then beat Hynes. He recalls what Hynes’s election attorney had said of him in 2001, when his rebellion seemed such a terrific threat. “John O’Hara,” he said, “has built his own little machine here, hasn’t he?” If it was a revelation then, it’s a lesson plan now.