HISTORICAL CONTEXT
EPISODE ONE: TEN PERFECT STRANGERS
“BOSS” TWEED & THE FIRST MACHINE
To understand what Alexandria Ocasio-Cortez was fighting against when she took on Joe Crowley & the Queens Democratic Machine, you have to go back. Way back. All the way back to 1852, to a young man who had just been appointed to the new, politically powerful New York County Board of Supervisors. From that office, young William Meager “Boss” Tweed would begin a decades-long career of large-scale graft and backroom politics. His first racket was simple: the Board was split by Democrats and Republicans, 50/50. Bribe one Republican and make every city contract pay an extra 15% to the Board of Supervisors — which really meant Tweed. And though he was a master political manipulator, his real power came via appointment to powerful boards and commissions where he could extract patronage and favors.
Much of his legacy would become famous via the fictionalized Martin Scorcese film “Gangs of New York” — rigging elections, importing out-of-towners to vote, bribing allies to vote multiple times at different locations, or even just literally stuffing ballot boxes with fraudulent votes. But his real skill was behind the scenes, in the smoke-filled-rooms of political deal-making.
By 1867, fifteen years later, Tweed’s power had grown — and his ambitions alongside it. He’d started using his political positions to enrich himself — he bought a printing press, and then used his influence to arrange so that it was the only press the city used. Bought a stationary company, and ran the same racket. His corruption was growing so intricate, he had to bring friends in to help manage it.
The “Tweed Ring,” as it became known, was composed of people who would become the city’s comptroller, the county district attorney, the “recorder,” along with a handful of active judges. Together, they could exert enormous power over the local bureaucracy.
But then he had his most audacious idea yet: reform the city charter completely. Tweed cozied up with good government groups to propose a new city charter, quickly passed, which would bring power to the Democratic-controlled City Hall, where Tweed’s allies had control. The Boss was shameless in his approach, paying $25,000 in bribes to Republic politicians to buy their votes in favor of passing the new charter— more than $600,000 in 2025 dollars.
Even at the time, local reporters were suspicious. According to one article from April 13th, 1871 in the New York Times, “this bill of Mr. Tweed’s destroys all publicity, all discussions, put the whole gigantic subject [of taxation] into the hands of four men who act upon it in [a] secret conclave, and practically tax us without limit, and then spend the money in any way they please and publish no accounts.”
And that’s exactly what happened.
The new charter gave Tweed enormous control over the city’s budget. He & his allies are said to have stolen between $2-$10 million dollars — what would be $50 to $200 million in 2025. At one point, he was the third largest landowner in the whole city.
Over the years, Tweed’s power and influence would only grow, even as he rarely held prominent offices himself. Elected to the New York State Assembly in Albany in 1868, Boss Tweed would use all the levers of power available to him. At one point, he pushed to get John T. Hoffman, a former protege, elected to the governor’s office.
Tweed became so powerful that he started to gain notoriety, infamy — celebrity. He didn’t care what was written about him. Who read the papers, anyway? But when a cartoonist named Thomas Nast started drawing satirical cartoons mocking the Boss — that’s when Tweed got mad. “I don’t care a straw for your newspaper articles,” Tweed was quoted as saying in a piece from the time, “my constituents don’t know how to read, but they can’t help seeing them damned pictures.”
Tweed would die just a a decade later — arrested in October 1871 for his voluminous corruption, he was found guilty in 1873 and sentenced to 12 years in prison. But two years later, ever the charming sort, he managed to escape prison by bribing officials. He’d make it all the way to Spain by way of Cuba — before local police happened to recognize & arrest him. He was extradited back to New York City, where he would die of pnuemonia in prison soon thereafter, in 1878.
And the Spanish cops who arrested him? They’d seen the cartoons that Thomas Nast had drawn — so popular, they’d been reprinted all the way in Spain. They recognized the old Boss immediately. (Records don’t state whether or not those Spanish police officers could even read. But as Tweed understood, sometimes a picture’s worth more than a thousand words.)
THE SURROGATE COURT SYSTEM
But none of Tammany Hall’s graft, bribery, or racketeering was as profitable or long-lasting as the system they designed in the Surrogate Courts.
When the poor and middle-class died, they would often leave small estates with no wills to determine how these assets should be distributed. Machines like Tammany had perfected a system of reaping the benefits. Mayor Fiorello La Guardia — who would do more to reform and diminish Tammany Hall’s corruption than any other man in New York City history — called it “the most expensive undertaking establishment in the world.”
Franklin Delano Roosevelt was elected president of the United States in 1932, at the height of the Great Depression. A longtime opponent of Tammany politics, FDR immediately used his executive power to eliminate federal money funneling into their patronage operation. When Fiorella La Guardia was elected to the mayor’s office the following year, 1933, Tammany Hall would finally see its fifty-year dominance of New York politics begin to come to a close.
La Guardia would pass a new city charter that would drastically decrease the power Tammany Hall exerted over local politics and businesses. It would create the powerful Board of Estimate, wresting control from a City Council dominated by Tammany cronies. La Guardia created new tests for many civil service jobs to ensure basic competency and eliminate patronage positions, and filled the city’s appointed offices with new civil servants outside the control of the old power structure. In just a few short years, Tammany’s power in the city had been massively curtailed.
But they still had control of the Surrogate Courts.
By 1938, the corruption had started to gain attention from the city’s good government proponents. The New York Bar Association called for a merger of the Surrogate Court and the Supreme Court to eliminate the inherent corruption — history would repeat itself often in the coming decades, as attempts to eliminate this nakedly corrupt and politicized system failed time and again.
The Americans for Democratic Action made an attempt in 1948; a commission focused on the Tammany Hall corruption suggested eliminating the courts entirely in the 1950s. In the 1960s, it looked like something might finally get done: A group called “Citizens Union” wanted to abolish the most obvious place for fraud or exploitation to occur: when minors, widows, or the intellectually disabled were the claimants. New York’s new Senator, Bobby Kennedy, got behind it, calling the Surrogate Courts “a political toll booth exacting tribute from widows and orphans.” Kennedy would go onto argue that replacing the current system with salaried public bureaucrats would “eliminate patronage from the Surrogate Courts and dry up a major source of sustenance from the worst elements in our political parties.” But the local machine fought back — hard — and nothing ever came of these efforts. (Read more about this whole system, in this excellent piece from the Gotham Gazette by Gary Tilzer, “Surrogate Court and Why It Should Go.”)
How little has this whole system changed? That article by Gary Tilzer? It’s more than twenty years old.
The Manhattan Surrogate Court system was integral into the financial health and longevity of the Tammany Hall political machine — and a hundred years later, history would repeat itself once again when the power brokers of the Queens Democratic Party constructed a similar system.
THE QUEENS MACHINE
By the end of the 20th century, the machines had transformed. The city’s ethnic character had shifted profoundly throughout the century, and with it, new ethnic enclaves had sprung up, with their own mutual support networks and political centers of gravity. Some would merge with existing machines — others would supplant them entirely. In places like Astoria, Queens, where the ethnic character was still largely intact, the machine had gotten old, and weak — and a corruption scandal provided a new generation of power brokers with a unique opportunity.
Tom Manton became the Queens County Democratic Party chairman in 1986. When the previous regime got caught in a scandal involving the Bureau of Parking Violations, the whole operation came apart, ending tragically in the suicide of former Borough President Donald Manes. Manton was a former U.S. Congressman and NYPD Officer, also spending time in City Council.
Soon, he was making moves straight out of the old Boss Tweed’s playbook.
When Surrogate Judge Louis Laurino was set to retire, Manton timed the resignation to one week after the deadline to deliver petitions for candidates to get on the ballot. Manton handpicked the judge’s successor, and soon his law firm, Manton, Sweeney, Gallo, Reich & Bolz were being assigned cases in the Surrogate Court.
But they didn’t stop there. Soon, Gerard Sweeny — Manton’s partner — was named counsel to the Queens Public Administrator, a position he still holds to this day. Reporting from Chris Bragg in New York Focus estimates he’s earned upwards of $30 million to date from this position.
To maintain control, the law firm keeps a close connection with the Queens Democratic Party. They offer free, pro bono legal service to all party-endorsed candidates. They’re well known for being experts at challenging petitions to keep primary challengers off ballots. And while representing poor New Yorkers in Surrogate Court, they’ve built a parallel business representing banks in foreclosure cases against working class homeowners.
Manton could not maintain control forever, though. So in 1998, he ensured that his handpicked successor would take over his Congressional seat, and — eventually — his role as leader of the Queens Democratic machine.
He used an old trick he’d used with Surrogate Judge Louis Laurino, waiting until after the petitioning deadline to announce, allowing him to hand pick his own successor. As Ross Barkan would contextualize a decade later for the Village Voice, “By waiting so late to make his announcement, Manton ensured only one elected official could compete in the Democratic primary to replace him. Since petitions had already been circulated, a candidate needed to be picked by a committee within the Queens Democratic Party that, of course, Manton exercised absolute control over. The committee met secretly, not allowing other elected officials to submit their names for consideration.
The person Manton had hand-picked? A 35-year-old State Assemblyman named Joe Crowley.
The system that Manton and Crowley created is alive & well today, with figures like Judge Peter Kelly — who is the subject of the long, well-reported New York Focus piece “In Fight Over Fortune, a Young Man Takes on the Kingmakers of Queens,” — perfectly exemplifying it in practice. Raised by a mother who was a Democratic Party district leader and a father who served as president of the party’s clubhouse in Astoria, in many ways Judge Kelly is a product of the machine politics of yore. Kelly’s sister, Ann Anzalone, was Crowley’s district chief of staff starting in 2001, where she served for almost two decades. Kelly got hired as a law clerk to a Queens Supreme Court Judge, where he would meet Gerard Sweeney.
According to Bragg’s reporting, “When Queens Democrats held their judicial nominating convention in August, the party’s seven selections for vacant state supreme court posts rose for acceptance speeches. One by one, each of the seven jurists singled out three men to thank by name: Gerard Sweeney, Michael Reich, and Frank Bolz.”
To this day, two-thirds of the panel who interviews judges seeking party endorsements in Queens — Michael Reich and Frank Bolz.
“Boss” Tweed was actively hostile to democracy — distrustful of the electorate, obsessed with maintaining power at all cost. In that way, his legacy is alive and well in Queens. “I don’t care who does the electing,” Tweed once famously said, “as long as I do the nominating.”
It’s a legacy no one should want to imitate.