A Chelsea block lined with brothels in the 1870s

Today, 27th Street between Sixth and Seventh Avenues is kind of a mishmash of wholesale business and small shops anchored on the western end by the Fashion Institute of Technology.

It was a different world in the 1870s, when the block ground zero for prostitution, with 22 houses of ill repute lining both sides of the street.

That’s in addition to dozens of other brothels on nearby blocks. This was the city’s post–Civil War neighborhood of vice, called the Tenderloin, a sinful stretch of 23rd to 42nd Streets between Sixth and Eighth Avenues.

The brothels of 27th Street were so notorious, they scored a mention in The Gentleman’s Companion, a guide to prostitution published in the 1870s, reports Andrew Roth in his book Infamous Manhattan.

Among the proprietors listed in the guide are “Mrs. Disbrow, 101; Mrs. Emma Brown, 103; Miss Maggie Pierce, 104; Joe Fisher, 105; Miss Dow, 106; Mrs. Standly, 107,” writes Roth.

Number 107, in the photo, is noteworthy because it’s the only original building left.

“Evidently the author of The Gentleman’s Companion didn’t think too much of the place, since his only comment is ‘the Ladies boarding-house at 107 West 27th St. is kept by Mrs. Standly and is very quiet.'”

“Not much of an endorsement, but better than the review received by her next-door neighbor . . . of which he warns that ‘the landlady and her servants are as sour as her wine,'” adds Roth.

Chatham Square: home to the city’s whorearchy

In the 1820s, it was an open-air market for horses and dry goods bordering a genteel neighborhood of row houses (as seen here, in an illustration looking back on 1812).

By the 1850s, Chatham Square was kind of the Times Square of its day, a seedy district of flophouses, taverns, cheap merchants, and the city’s first tattoo parlors on the outskirts of the East Side’s notorious Five Points slum.

How seedy was it? Describing the prostitution rampant there in his book City of Eros, Timothy J. Gilfoyle writes:

“Along its western edge, the Bowery and Chatham Square were a bourse of sex. The patrician George Templeton Strong claimed that after nightfall, amid the theaters, saloons, dance halls, and cheap lodging houses, the thoroughfare overflowed with ‘members of the whorearchy in most slatternly deshabille.’

“Once elegant eighteenth-century residences like that of the merchant Edward Mooney at 18 Bowery now served as brothels.”

Like everything in New York, the red-light districts change as well. Prohibition, the Depression, a growing Chinatown, and slum clearance all remade Chatham Square into a messy but not sleazy intersection off the Bowery.

It’s now known as Kimlau Square, which honors American servicemen of Chinese ancestry who died for their country.

[Above photo: an 1853 Daguerreotype of Chatham Street, now Park Row, looking toward the Square]

The thieving street walkers of 1870s Soho

“Strangers visiting the city are struck by the number of women who are to be found on Broadway and the streets running parallel to it, without male escorts, after dark,” wrote James D. McCabe in his 1872 guidebook Lights and Shadows of New York Life.

“They are known as Street Walkers, and constitute one of the lowest orders of prostitutes to be found in New York.”

“They are nearly all thieves, and a very large proportion of them are but the decoys of the most desperate male garroters and thieves.”

One common scam, McCabe explains, was for a street walker to lure a tourist to her room in one of the subdivided “bed houses” in today’s Soho.

There, the street walker and a male confederate would rob the tourist while threatening his life.

Another trick was what McCabe called “panel thieving”:

“She takes her victim to her room, and directs him to deposit his clothing on a chair, which is placed but a few inches from the wall at the end of the room. This wall is false, and generally of wood.”

While the street walker and customer do their thing, a male thief will quietly slide out from behind the fake wall and lift the customer’s wallet.

The sucker won’t realize what has happened until he is out on the street, the street walker and her co-conspirator long-gone.

A New York street helps coin the term “hooker”

Corlears Hook was named in the 17th century for the Van Corlears family, early Dutch settlers who had a farm near this spit of land jutting into into the East River.

In the 18th century, the British renamed it Crown Point (on the 1776 map below), and in the 19th century it reverted back to its New Amsterdam moniker.

But it wasn’t farmland anymore. By the 1830s it became the city’s most notorious red-light district, attracting sailors and the women who serviced them.

The women of Corlears Hook
“. . . where the lowest and most debased of their class. They were flashy, untidy, and covered with tinsel and brass jewelry,” states Seafaring Women, by David Cordingly. “Their dresses are short, arms and necks bare, and their appearance is as disgusting as can be conceived.”

“The latter area is generally credited with giving rise to the term ‘hooker’ and certainly had its fair share of rough characters, male and female,” adds Cordingly.

By the 20th century, Corlears Hook had become a lovely park, which today offers views of the Brooklyn and Manhattan Bridges—and no hint of its importance in creating a popular term for ladies of the night.

A 1970s proposal to legalize prostitution

You know the story: After Times Square’s heyday through the 1950s, it slid into seediness and decay.

By the early 1970s, West 42nd Street was packed with sleazy characters, leaving the people who made their living in the Theater District feeling unsafe.

So a group of 62 performers came up with a radical idea.

They sent a letter to Mayor John Lindsay proposing that the city create a legal red-light district, where the “prostitutes, pimps, perverts, and panhandlers” who made Times Square so dangerous could ply their trade.

Needless to say, Mayor Lindsay vetoed what he called a “drastic suggestion,” according to a New York Times article on August 9, 1972:

“[Lindsay] spoke of the ‘basic moral question’ of legalizing prostitution, the perhaps insoluble task of finding a location for such a district and the additional problems of controlling the influx of prostitutes that would result from legalization.”

Lindsay’s plan was to have law enforcement beef up the arrests of streetwalkers and padlock massage parlors.

But it took another 20 years—and a different mayor—to make a real dent in Times Square’s rep as a hooker haven.

Did Jack the Ripper kill a Bowery prostitute?

On April 23, 1891, Carrie Brown, a 60-year-old prostitute known as “Old Shakespeare” because of her penchant for quoting the Bard after a few drinks, took a customer to the East River Hotel.

The next morning, her body was found on the bed in room 31 of the hotel, on Catherine and Water Streets. She had been strangled and disemboweled. 

Her brutal murder riveted New Yorkers, and newspapers instantly raised the possibility that she could be the first U.S. victim of Jack the Ripper, who was killing prostitutes across the Atlantic in London around the same time.

Because of the fear Jack the Ripper whipped up in the city, New York cops felt a lot of pressure to solve the case.

So they arrested an Algerian, Ameer Ben Ali, who lived in an adjacent room at the East River Hotel.

Though the evidence against Ali was circumstantial, he was convicted of second-degree murder and sentenced to life in prison.

Eleven years later, after police reformers presented the city with evidence that the cops framed Ali, he was set free. 

The real killer, like Jack the Ripper, remains a mystery.