‘Boss Tweed’ Attacked the NYTimes Exactly the Way Trump Might

The Times’s publisher issues a warning about Trump. Eerily same tactics were used 150 years ago — against his own paper.

Donald G. McNeil Jr.
12 min readJan 20, 2025

A.G. Sulzberger, the publisher of The New York Times, gave a talk last week to the Silurians, a club for superannuated journalists of which I am a member.

A.G. Sulzberger at a Silurians lunch on January 15, 2025
A.G. Sulzberger at a Silurians Club lunch, January 16, 2025

His topic was “Why Press Freedom Is in Danger.” and he expounded on an op-ed he wrote last September in The Washington Post predicting how Donald J. Trump, if elected, might attack the press.

His opening paragraph was this:

After several years out of power, the former leader is returned to office on a populist platform. He blames the news media’s coverage of his previous government for costing him reelection. As he sees it, tolerating the independent press, with its focus on truth-telling and accountability, weakened his ability to steer public opinion. This time, he resolves not to make the same mistake.

Sound familiar? Mr. Sulzberger was actually describing Viktor Orbán of Hungary, but his point was that, in democracies, authoritarian leaders can’t just resort to crude brutality. Unlike Vladimir Putin, they don’t have reporters shot or beaten to death in their apartment buildings. Unlike Xi Jinping, they don’t jail them for years on inane charges like “picking quarrels.”

Instead, leaders like Orbán, India’s Narendra Modi and Brazil’s Jair Bolsonaro use the state itself to intimidate and bankrupt journalists who question their actions.

First they stoke hatred, calling reporters “fake news,” the “lamestream media” or “enemies of the people.”

Second, they sue over every investigative article and encourage their deep-pocketed supporters to do the same. Even if the suits ultimately fail, they cost millions in legal fees, which many small papers can’t afford.

Third, they buy or seek control over critical media outlets, or help their rich supporters do so.

Fourth, they weaponize the state’s powers: they threaten to cancel broadcast licenses, for example, or to bring anti-trust charges against media companies or to subpoena reporters’ phone and computer records in a hunt for their sources.

For example, Mr. Sulzberger said, in 2023, shortly after the BBC aired a documentary accusing Prime Minister Modi of having encouraged Hindu extremists during 2002 ethnic riots, the network’s offices in Delhi were raided. The pretext was a hunt for violations of India’s notoriously complex tax code, but the police locked out the staff and seized their phones and computers, presumably searching for the BBC’s sources.

Mr. Sulzberger didn’t mention it, but it all sounded vaguely familiar. An eerily similar bureaucratic, legal and populist assault on a newspaper by an angry and powerful politician is described in Chapter III of History of The New York Times, 1851–1921 by Elmer Davis. (The in-house history was commissioned by Adolph Ochs, Mr. Sulzberger’s great-great-grandfather, for the 25th anniversary of his purchase of the paper. Mr. Davis was a Times staffer, but it’s still quite a lively book.)

The chapter is titled “The Times and the Tweed Ring” and it contains such weird echoes of the battle that would take place 150 years later between The Times and Donald J. Trump that it feels as if it was penned by Nostradamus or an author of dystopian science fiction. Some disturbing tactics it describes, like posting the home addresses of publishers and editors and mildly suggesting that supporters “visit” them, have been re-used very recently.

William M. “Boss” Tweed in a photograph by Matthew Brady

From 1858 to 1871, William M. “Boss” Tweed, Grand Sachem of the Tammany Hall Democratic machine, was the dominant power broker in New York city and state politics. He was also arguably the most corrupt politician in the history of America.

He rose from the ranks of volunteer fire companies and violent street fights through ward politics to the board of aldermen. By 1870, through bribes, patronage appointments and a new city charter he had pushed through Albany, he controlled both the mayor and governor, the city aldermen and the state legislature, most judges and virtually every city inspector and auditor. The kickbacks he and his cronies demanded were almost unimaginably outrageous; by some estimates they made off with the equivalent of $8 billion today. The construction of a new county courthouse, for example, cost four times what Britain spent building Westminster Palace; Tweed bought quarries to provide the marble and slate at high markups and every laborer on site kicked back 50 to 85 percent of his salary. One carpenter, a Times investigation eventually revealed, received $360,000 for a month’s work.

In return for forcing through bills that helped 19th century corporate raiders like Jay Gould, Tweed became a part owner of the Erie Railroad, a gas company, two banks, and the printing firm that did all the city’s business. He was the proprietor of the Metropolitan Hotel, which accommodated 600 guests, and controlled the company that built the Brooklyn Bridge. He was the city’s third largest landowner, buying vast tracts in Yorkville and Harlem, having the city pave streets and run water lines, and then reselling at huge profits. When his thieving drove taxes up — the city’s budget was then on a pay-as-you-go basis — he had the legislature permit the sale of 30-year bonds, and a grateful populace saw its taxes go back down.

Republican business leaders saw through his plundering but stayed silent because Tweed also controlled the assessment board that set the property taxes on their mansions and factories. Most of the city’s newspapers also kept quiet for fear of losing the lucrative official advertising that, in those pre-internet days, government entities were required to publish.

Only The New York Times and Thomas Nast, the acid-penned political cartoonist at Harper’s Weekly, dared to publicly oppose the machine.

Nast got his material from Times articles. Tweed was quoted as saying he didn’t care what was written about him because his Irish immigrant constituents couldn’t read, “but let’s stop those damned pictures.”

Thomas Nast cartoon from Harper’s Weekly

When the Times investigation started in 1870, it had no hard evidence and merely asked repeatedly how a former fireman, the son of a Scottish chair-maker, had built such enormous wealth, and called for the city’s account books to be opened. The comptroller, Richard “Slippery Dick” Connolly, simply refused to do so, despite laws saying they were public property. “They were locked away,” Mr. Davis wrote, “as carefully as the golden plates of Mormon.”

Later that year, Tammany Hall easily beat a reform ticket made up of Republicans and independent Democrats. Accusations that Republican election monitors had been bought off by Tweed were never proven.

Rival papers attacked the Times, implying that it was driven by partisan malice, by Republican bribes or by its interest in a lawsuit against the city. The basis for the last accusation was this: in the 1860’s the Times had stopped taking municipal ads because they came with demands for silence. Tweed switched the account to the paper’s chief rival, Horace Greeley’s New York Tribune, but The Times sued for back payment for ads it had already run. (Tweed was notorious for not paying his bills.)

Tweed’s boosters argued that, by disparaging city officials, The Times was being unpatriotic. Criticism, they said, hurt New York’s good name and its credit with banks.

Just before the election, Comptroller Connolly allowed an inspection of the books by a committee of six respected business leaders, including John Jacob Astor. They certified them “faithfully kept.” (Bizarrely, they did not question the fantastical wages paid to laborers or the fact that checks for millions of dollars were cashed by just a few signers.)

After the election, Tweed began a multi-pronged attack on The Times. He tried to amend the criminal code to give judges greater latitude to hold defendants in contempt of court. (In an earlier case involving the Erie Railroad, a Tweed-appointed judge had tried to get a grand jury to indict the Times’s owners.). His men falsely told other papers that the Times building on Park Row, erected on the former site of the Brick Presbyterian Church, had a deed restriction saying it could be used only for church purposes.

Then he actually tried to buy the paper. The Times had been founded in 1851 by Henry Jarvis Raymond and George Jones, both of whom had been protégés of Greeley when he founded the Tribune in 1841, although Mr. Jones later left to become a banker. Mr. Raymond, the Times’s crusading editor for its first 18 years, had died suddenly in 1869, at age 49. (His Times obituary said he died at home of “an attack of apoplexy.” There were other rumors, including one that he had collapsed while out with friends who assumed he was just drunk, and another that he had actually died in the apartment of the actress Rose Eytinge. But there was never any suggestion of Putinesque foul play.)

In those days, only 100 shares of New York Times stock existed. Mr. Raymond had owned 34 and Mr. Jones, 30. Mr. Raymond’s heirs wanted to sell. Tweed formed a company that included members of his ring, the Wall Street raiders Jay Gould and Jay Fisk, plus a couple of well-known reformers, including Peter Cooper, to act as cover. They promulgated rumors that the paper was losing advertising and nearly bankrupt. Mr. Jones published a statement denying that, saying “No money that could be offered me should induce me to dispose of a single share of my property to the Tammany faction, or to any man associated with it, or indeed to any person or party whatever until this struggle is fought out. I have the same confidence in the integrity and firmness of my fellow proprietors.”

Then The Times had a stroke of luck. In December 1870, the County Auditor, a central figure in the Tweed ring, had been killed in a sleigh accident. His place was taken by the County Bookkeeper, who was affiliated with James O’Brien, leader of a Democratic faction on bad terms with Tweed. Mr. O’Brien eventually leaked to the Times records showing that 90 percent of the money spent on the county courthouse had been stolen, and that similar frauds had taken place in renting and furnishing armories.

(That too had an historical echo: in 2018 and again in 2020, the internal records of the Trump family empire were leaked to the Times.)

By the summer of 1871, when Tweed realized what evidence the Times had, he tried a new approach: bribery. A lawyer friendly to Mr. Jones invited him to his office. On arrival, he found waiting Comptroller Connolly, who offered him $5 million to suppress the news. (That’s the equivalent of $130 million today. The after-tax profit of The New York Times company in its last annual report was $233 million, so it was quite a sum.)

Mr. Nast, the Harper’s cartoonist, later told a biographer he was offered $500,000 to stop drawing and take a grand tour of Europe.

According to Mr. Davis, Mr. Jones’ first response was “I don’t think the devil will ever bid higher for me than that.” Then he said no.

On July 8, the Times began printing stories about the armories. Before it began its major exposés on the courthouse, however, it made a self-protective move. To keep control out of Tweed’s hands, Mr. Jones announced in the paper, Colonel Edwin B. Morgan, a former upstate Congressman who previously owned just two shares of Times stock but was also an early investor in both the American Express and Wells Fargo companies, had just purchased the 36 shares held by Raymond’s heirs for $375,000. (That per-share price of $11,000 was almost double what had ever previously been paid for a Times share.)

On July 22, the Times began its big exposé under what Mr. Davis said was its first three-column front page headline. The “deck heads” below it used words previously employed only on the editorial page: SCOUNDRELS, SWINDLERS and THIEVES.

The Comptroller’s records were reprinted in minute detail, showing, for example, checks paid to “Philip F. Dummey” and cashed by firms that Tweed was known to own. It took several days to unload it all, and it was reprinted in a four-page Sunday supplement in two languages to also reach the city’s large German-speaking population. It sold so well that the press run was repeated until half a million copies were run off.

The Times’s stories were major news across the country and in London and Paris, but the other New York papers ignored them, other than Greeley suggesting that Tweed might sue for libel. Threats were made to arrest the accountant who had brought the books to Mr. O’Brien.

Tweed’s downfall began there, but it took years and had several causes. The Times’s revelations scared bankers away from lending to the city or buying its bonds, so funds to pay city workers dried up, and angry crowds of them formed daily in City Hall Park.

(Tweed retaliated: The Star, a minor paper in his pocket, published Mr. Jones’ home address and that of his editor Louis J. Jennings, “with a hardly veiled suggestion to city employees whose families were starving,” Mr. Davis wrote, “that these men were responsible for the stoppage of wages.”)

Separately, Tweed was further discredited by that summer’s “Orange Riot” in which Irish Protestants, with more than 5,000 police and National Guardsmen protecting them, marched provocatively through Irish Catholic neighborhoods celebrating the Protestant victory at the 1690 Battle of the Boyne. In the riot that erupted, 60 civilians were killed, 150 were wounded and Eighth Avenue was bathed in gore. Tweed was blamed because he had permitted the march and the use of troops who had shot and bayonetted dozens of participants in the melee.

In September, after a committee of 70 leading citizens was formed to investigate municipal graft, the Comptroller’s office reported that it had been robbed of all its records. It was later discovered that a Tweed man had burned them.

Then members of Tweed’s ring began turning on each other. Comptroller Connolly, realizing he was about to be made the scapegoat, cooperated with the investigators by appointing a reform lawyer as his deputy and then resigning. Tweed was arrested but made $1 million in bail. Some of his ring fled to Europe, and all those who stood for re-election that November were defeated. Tweed himself was re-elected to the State Senate but was stripped of his city posts and ousted as Tammany’s chairman. His first trial ended in a hung jury, his second convicted him on 204 counts and he served a year in jail. He then faced civil suits and was jailed when he could not post bond. During a home visit, he fled to Cuba and sailed as a common seaman on a ship bound for Spain. On arrival, he was recognized from one of Nast’s cartoons, sent back on an American warship and imprisoned in the Ludlow Street Jail. He died there of pneumonia in 1878 — and the mayor refused a request to fly City Hall flags at half-staff for him.

During the Q&A session at the end of Mr. Sulzberger’s presentation, I suggested that The Times might face major legal bills over the next four years and asked whether anyone was envisioning creating a fund for the defense of the First Amendment that wealthy, democratically-inclined Americans could contribute to.

He replied that small papers definitely needed help, and cited the case of Mississippi Today, which is being sued by a former governor for its Pulitzer-winning series accusing him of benefitting from a $77 million welfare scandal. For such outlets, he said, the Reporters Committee for Freedom of the Press is a resource that deserves support.

Some papers, including The Washington Post and The Los Angeles Times have billionaire owners.

As for The Times, he said it has been hoarding cash against a legal assault. (As of September 2024, according to its latest 10-Q, the company had $920 million in cash and marketable securities on hand, so he’s correct, although the Times has historically kept a big cash cushion on hand since it nearly went bankrupt during the 2008–9 recession.)

As an aside, a colleague at my Silurians table told me she had heard that the check for $392,638 that Mr. Trump was recently ordered to pay to The Times to reimburse it for legal fees in relation to articles alleging that he had evaded taxes would be displayed in the Museum at The Times. Following the old journalistic maxim “Never check out a great anecdote,” I didn’t.

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Donald G. McNeil Jr.
Donald G. McNeil Jr.

Written by Donald G. McNeil Jr.

New York Times, 1976–2021. Last beat: lead Covid reporter. 2020 Chancellor Award; 2021 NYT team Pulitzer donaldgmcneiljr1954@gmail.com

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