All week, we’re bringing you a series of deep dives into the surprising histories of storied addresses. Back to our usual after the New Year.

The exterior of the Ludlow Street Jail in 1895. (Source: Museum of the City of New York)

The exterior of the Ludlow Street Jail in 1895. (Source: Museum of the City of New York)

Christmas Day dinner at the Ludlow Street Jail in 1911 was outrageous. The Warden Thomas J. Rock served a lavish spread (turkey, sweet potatoes, celery, fruits, plum pudding, coffee, and even a Union-made cigar) and his prisoners, moved by their keeper’s kindness, presented Rock with something unexpected — a sixteen-inch silver loving cup, which they had managed to smuggle into the jail undetected. One prisoner, a lawyer locked up for failing to make alimony payments to his wife, stood to toast the Warden and gushed with sentiment.

“Our dear Warden,” the lawyer began, “while we are filled with good cheer and gratitude for all the comforts that have been showered upon us, a feeling of sadness comes over us, because we are approaching the day when we must say ‘Godspeed’ to you, through whose indefatigable efforts we have received so much consideration.”

Such was life for those behind bars at 70 Ludlow Street, which once stood at the corner of Ludlow Street and the now-vanished Essex Market Place. Today that address is no more. Seward Park High School, a city block-sized building at 350 Grand Street that’s now called Seward Park Campus, replaced the Ludlow Street Jail in 1928, as well as a row of tenement houses, a city courthouse and second jail, an open air market, and older public school. For 65 years before that, the Ludlow Street Jail, which was otherwise known as the New York County Jail, remained a salacious hotbed of government corruption and strangely placed opulence, whose prisoners — at various times people accused in either civil cases or federal criminal cases — are thought to still haunt the halls of one of New York City’s finer public educational institutions.

It’s a story best told through two jailbreaks, 20 years apart — one by a group known as the Post Office Burglars; the other by the infamous William M. Tweed, who ran the city’s Democratic political machine at Tammany Hall.

When Boss Tweed broke out of the Ludlow Street Jail on December 4, 1875, he was facing charges of embezzling $6 million from the State of New York. To escape, he had neither of his cell, nor swiped a set of keys off an unsuspecting guard, and he certainly hadn’t from an abutting tenement house (each being various methods of escape over the years). Tweed had instead, with express permission from the Warden, simply walked out the front door.

Taken from an 1897 Sanborn Map Fire Insurance Map. (Source: New York Public Library)

Taken from an 1897 Sanborn Map Fire Insurance Map. (Source: New York Public Library)

Directly behind Tweed, the jail’s red Philadelphia-brick walls rose 60 feet above Ludlow Street and continued around the southeast corner of the block to face the open-air Essex Market. The L-shaped building’s facade, the New York Times wrote in 1868, “was not unlike those of our plain church edifices.” And if it weren’t for the iron-barred windows, the passerby, shopping for dinner across the street, might mistake the building for “a Friend’s Meeting House, or an old-fashioned Methodist Church.” Ludlow Street, however, was no house of God.

A sketch of the Ludlow Street Jail from 1885. (Source: New York Public Library)

A sketch of the Ludlow Street Jail from 1885. (Source: New York Public Library)

Embedded into its red brick, beside the jail’s “ponderous” iron front door, was a white marble plaque into which Tweed’s name, along with the names of several other city officials, had been carved. Tweed was a member of the Board of Alderman (a predecessor to the New York City Council) that had in 1859 on a vacant, city-owned lot. Designed by , an architect for the Building Department, the jail opened on July 22, 1862, and replaced the ill-conceived Eldridge Street Jail as the county’s main facility. The Times called it a “model building.” What went on inside was another story.

The New York Tribune would expose the absurdities of the Ludlow Street Jail in an undercover report in 1871. The reporter, who signed his May 30 article with the pen name Poor Prisoner, quotes a then-editor of the Tribune, Johnny Weinheimer, proposing the piece to him. “I have reason to suspect that there is something rotten in Mr. Warden Tracey’s state of Denmark, and I want you to go to Ludlow-st. and find out for me whether such be really the case. I think arrangements can be quietly effected which will make you temporarily an inmate of the prison. Have you any objections…?” Poor Prisoner had none.

His article was the first of numerous pieces published by both the Tribune and Times in the following months and years that revealed the sheriff and his warden were running a less-than-reputable operation. Most prisoners locked up at Ludlow Street were delinquent debtors. Their creditors had complained to judges, and in turn those judges had granted warrants that were then executed by the sheriff. Many people criticized the process, arguing that it gave “greedy creditors” the power to unfairly punish people for being unable to pay negligible sums. But the sheriff and warden were just following the rules when they arrested and detained people, respectively. At Ludlow Street, their misdeeds became more apparent.

The warden’s job was unsalaried, and he made his living by charging prisoners anywhere from $10 to $30 a week to “board” at his jail. Already in debt, most incoming prisoners couldn’t cough up the cash. The warden declared them destitute and marched them up to the jail’s poorly kept top floors, where, as the Times described in 1878, “the atmosphere increase[d] in density and foulness and the cells [became] more and more uncomfortable.” If the jail’s 87 cells were already full, an incoming prisoner would be forced to share a cell with two others. And the three would need to decide who would sleep in the cell’s two iron beds, with their filthy blankets and pillows, and who would get the insect- and vermin-infested floor.

Those who could afford the boarder’s fee enjoyed a drastically different experience. A prisoner could, the Times wrote in 1873, “have all the delicacies of the season if he [paid] the Warden’s price.” He could play billiards all day (yes, there was a pool table inside the jail) or chess or backgammon or card games. He could read the day’s paper in the jail’s library or “smoke cigars, crack jokes with the keepers, lounge in the lower day-room, and at the appointed hour dine in a nicely furnished apartment,” all for “C.O.D. (cash on demand).” And if none of this suited the paying prisoner, he could spend his days drinking lager beer or whiskey bought at the “Hole in the Wall” — a bar and general store found in one of the jail’s vacant cells. “A fitting sign for the front of this building,” remarked one warden, “would be ‘verily, the way of transgressors is easy.’”

Sketches of life inside the Ludlow Street Jail. (Source: Harper’s Weekly/New York Public Library)

Sketches of life inside the Ludlow Street Jail. (Source: Harper’s Weekly/New York Public Library)

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None, however, had it quite as good as Boss Tweed. He lived in a two-room suite on the building’s first floor — the warden’s sleeping chambers and office, which Tweed used as a private dining room — and paid the warden handsomely for the privilege. For $125 a week, Tweed could also occasionally leave the jail to visit his family at home. Home was where Tweed was headed on that December day in 1875. He disappeared shortly after and didn’t reappear until two years later, when Spanish authorities found him working on a merchant ship in Spain, promptly arrested him, and turned him over to the U.S. government. On April 12, 1878, Tweed would die of pneumonia, back in his suite on Ludlow Street.

Twenty years after Boss Tweed’s escape, on July 4, 1895, Henry Russell, Charles Allen, and Joseph Killoran, a “spectacular and enterprising trio of Post Office burglars,” burst forth from the jail’s front door brandishing what were believed to be pistols (they were actually iron pipes). Following a brief chase by the guards, they disappeared into the surrounding tenements. Their escape was national news, and the investigation and trial that followed would make the New York County Sheriff at the time, Edward J.H. Tamsen, a household name across the country.

Tamsen oversaw a dizzyingly corrupt institution, which had been the target of numerous investigations by various government bodies since the Tribune’s first exposé in 1871. Government investigations in 1871, , , 1883, 1884, and collectively found the Ludlow Street Jail to be structurally insufficient. It was plagued by a perpetual dampness and punctured with easily managed escape routes. The jail’s management was similarly derided, not only for the extortion of its prisoners but for the absence of any proper record keeping whatsoever by the warden or the sheriff’s office. Beyond the filth, graft, and injustices within the jail, investigators also laid bare the further misdeeds of a succession of sheriffs.

The sheriff charged the State anywhere from 50 cents to $1 for every prisoner he kept, which made running the jail a lucrative and easily corruptible business. For example, the 1884 investigation, led by then New York State Assemblyman Theodore Roosevelt and with hearings held in Boss Tweed’s former Ludlow Street quarters, found that the sheriff at the time had illegally taken $75,000 from the State through fraudulent vouchers. Six years later, a grand jury investigation linked the Sheriff’s Office to Tweed’s former dominion, Tammany Hall, and revealed the sheriff was funneling money to Tammany in the form of gifts and kickbacks.

Five years later, in 1895, Tamsen was on the stand, having been indicted following the Post Office Burglar’s escape. And yet Tamsen, despite the bad publicity during his tenure, was perhaps Ludlow Street’s best jailer. He had issued a set of strict rules — what he called his “10 Commandments” — the effects of which were noted by one reporter as producing “a different air around the jail.” During his trial, . James P. Archibald, who was the jail’s new warden (the warden who had allowed the Post Office Burglars to escape had promptly been replaced), would at the same trial illuminate for the court the real problem, beyond all else, that had plagued the institution: its federal prisoners.

A sketch of the Ludlow Street Jail from 1885. (Source: New York Public Library)

Julius Wilcox. Ludlow Street Jail. 1892 (Source: Brooklyn Public Library, Brooklyn Collection)

Along with the civil cases (the prisoners convicted and awaiting court appearances in civil suits, a majority of whom were debtors) were the alleged criminals — the murderers, counterfeiters, embezzlers, mutineers, Civil War deserters and rebel captives (in the jail’s early years), political conspirators, obscene content distributors, insurance fraudsters, and bank robbers. Roughly one in ten of those being held (the ratio varied over the years) at Ludlow Street was a prisoner of the U.S. government, charged with a federal crime.

Victoria Woodhull, the suffragist and first woman candidate for the Presidency of the United States, was one notable federal inmate, arrested for sending a labor reform and women’s suffrage newsletter through the mail. James D. Fish, who embezzled the accounts of his Marine National Bank and famously bankrupted former U.S. President, Ulysses S. Grant, was another. And then there were the Post Office Burglars, arrested in New York after robbing a post office in Springfield, Illinois of $5,000 in postage stamps and an unspecified quantity of wedding silverware belonging to the Postmaster’s daughter.

There was no need, Warden Archibald argued, for civil prisoners, “usually harmless unfortunates,” to be exposed to federal prisoners who were “steeped in vice and poisoned by it.” While Archibald would fall from grace a year later (he would be arrested after being found unconscious on the floor of a bar on 42nd Street following a night of heavy whiskey drinking and fired soon after) his argument held sway. Within two decades, the reform that began with Tamsen (who was eventually acquitted) along with the permanent removal of federal prisoners from the jail in 1904, would render the Ludlow Street almost unrecognizable.

By the time that Christmas dinner rolled around in 1911, the jail had become a home for alimony debtors. Most prisoners were locked up for being deadbeats to their current or former spouses, and they loved it at Ludlow Street. It was home away from home, with comforts so enticing that six of its mere 15 prisoners had decided to stay through Christmas even though their sentences had been served. Two former prisoners, who had “plenty of money and amusement unlimited awaiting them outside,” actually came back to the jail to enjoy that Christmas spread.

(An illustration of the Ludlow Street Jail from 1925. Source: The New York Times)

(An illustration of the Ludlow Street Jail from 1925. Source: The New York Times)

The lawyer-inmate, in offering up the inmates’ gift to the warden, rambled on about the jail’s “utopian conditions” and how far it had come from the days when it was a “hotbed of corruption,” “an institution that was founded by a grafter and in which corruption was reared for many years.” So touched was the warden that he temporarily suspended his strict rules against accepting gifts from prisoners and took the loving cup down to his office to place it on a desk that once belonged to the very grafter to which the lawyer referred. None other than Boss Tweed.

The apparent farce at the Ludlow Street Jail continued. The next warden to preside over what people derisively called the “Alimony Club” or “Hotel de Ludlow” was a fervent musician who brought with him “two violins, a cornet, a French horn . . . a redheaded Brazilian parrot, which he [had] taught to sing several songs, and two warbling canaries, whose high notes [topped] high E.” The guests of Hotel de Ludlow would perform concerts and local theater companies produced jailhouse plays. Such remarkable conditions would lead the sheriff, visiting Ludlow Street in 1912, to be by the absence of the “sunken eyes” and the “wailing or curses” found in the City’s other prisons.

The Ludlow Street Jail’s musical warden. (Source: New York Tribune)

The Ludlow Street Jail’s musical warden. (Source: New York Tribune)

In the end, it was high cost that doomed the Ludlow Street Jail. By 1915, the sheriff had turned against the jail, calling it a “standing joke” — and with a maintenance bill of $50,000 a year, an “expensive joke for the city,” at that. The next sheriff, the jail’s last, wanted to put the place up for auction, exclaiming that the county “could maintain the Ludlow Street prisoners more cheaply at a hotel.” Times that the jail had become “an elephant on the hands of the city, eating bails of the taxpayers’ hay and being altogether the most expensive jail in this or any other city” in the country.

Neither the governor nor a reformed sheriff’s office dealt the jail its final blow –a coterie of school children did. Since the start of the 20th century, there had been mounting pressure from the Board of Education for the City to tear down the jail, as well as the police court, tenement houses, and school, PS 137 (which had been erected at some point on the site of Essex Market) that took up the entire city block. The plan was to replace it with what the Associate Superintendent of Schools in 1904 called a “skyscraper” school. In 1924, a delegation of New York City children met with Mayor John Francis Hylan and handed him a petition signed by 40,000 residents of the Lower East Side requesting the jail be torn down. One member of the delegation, a schoolgirl named Gussie Cohen, told Mayor Hylan that she thought it would be right to “demolish a monument to crime and to erect a monument to learning.”

And so was set in motion the approval of a new public high school (the first building below 14th Street to be used solely as a public high school) by the New York State Board of Estimates on July 3, 1925, a day short of the 30th anniversary of Post Office Burglars’ brazen escape. The Ludlow Street Jail closed down two years later on December 24, 1927. Its prisoners were moved to the old 22nd Precinct Police Station on West 37th Street, whose facilities “were larger, cleaner, roomier, and better generally.”

The City would break ground for Seward Park High School in 1928. A year later, several thousand residents of the Lower East Side would attend a ceremony where Mayor Jimmy Walker laid the new building’s cornerstone, in which a copper box containing copies of the prior day’s newspaper, specifications for the building, a Bible, and an American flag were placed. From that cornerstone would extend a storied institution whose halls would shape the minds of generations of graduates, among which Jerry Stiller, Walter Matthau, four New York Supreme Court Judges, a Nobel Prize winner, and a Harlem Globetrotter are just a notable few. The school continued until 2006, when its last class graduated and the five smaller public high schools that make up Seward Park Campus took over.

A program from the cornerstone laying event.

A program from the cornerstone laying event.

These days, the kids around Seward Park Campus like to share rumors about the jail. Many are convinced the building itself used to be the jail. Others hear that 350 Grand Street was a mental institution, while most agree that parts of its city block-sized basement — particularly the pool and locker rooms — have a suspiciously dungeon-like feel. The kids like to tell one story about a set of stairs in the cellar, where students on their way to detention are liable to get snatched by the ghosts of prisoners, dragged off to a much more permanent incarceration.

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It’s easy to see how imaginations can run wild on a site with such a salacious past. The boys’ locker room, with its wire-mesh walls and group shower, has a seriously jail-like feel.

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The pool, unchanged since the building opened 86 years ago, has that bygone look. The school’s present day custodian, Rick Giuseppe, who affectionately calls the shower “the gang shower,” says a rumor is all it is.

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Sure, there’s plenty of history in the basement: a records room with every student record going back to school’s founding; the length of an old rifle range that was used during World War II; dormant coal-fired, hammerhead boilers painted with colorful faces by their fireman years ago. But all that’s left of the jail is the story the kids tell. And maybe the ghost of a lingering alimony debtor, eating his Christmas pie.

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Correction: Due to an editing error, the original version of this story misstated the date of the photo provided by the Brooklyn Public Library. It depicts the jail in 1892.