Flatiron’s red-light district past explored in historic walking tour

This building on Sixth Avenue and 24th Street was once home to Koster & Bial, a music hall where scantily clad dancers would spend time with guests in private rooms. (Photos by Sabina Mollot)

By Sabina Mollot

While these days, the neighborhoods of Flatiron and NoMad are known for their newly built, trendy hotels and an increase in families moving into the neighborhood, what few who even live there know is that at one time it was home to numerous houses of ill repute, gambling dens and saloons.

This was during an era that spanned from about 1870 to 1910, with the area then commonly known as the Tenderloin. It was also called Satan’s Circus, or at least it was by the Tenderloin’s most vocal critic, Reverend Charles Parkhurst of the Madison Square Presbyterian Church, while slamming it in a Sunday sermon.

Over a century later, that swath of the city can still be explored — or at least the area that once housed those infernal brothels as well as hotels and dance halls where much of the action took place — through a weekly walking tour.

The tour, coordinated through the Museum of Sex on Fifth Avenue, is led by Robert Brenner, a veteran New York tour giver. He is also an almost 30-year resident of Chelsea, in a section of the neighborhood that was once within the confines of the Tenderloin, the boundaries of which have shifted over the decades.

The district is largely defined as being from 23rd to 42nd Street between Fifth and Seventh Avenues though it has sprawled as far north at Central Park at points and as far south as 14th Street, as far east as Madison Avenue, and as far west as Eighth Avenue.

The participants that gathered for the most recent “Satan’s Circus” historic walk were all local, as they also tend to be on Brenner’s other, sex-themed tours. (He does one of a small, defunct Jewish red-light district on the Lower East Side and one for that one-time mother of all red-light districts, Times Square.) But those who come to Satan’s Circus will get to see very little in terms of real estate. As the tour wove its way through streets clouded in construction dust last weekend, it was clear that little evidence of the Tenderloin, where over 4,000 people were once employed as prostitutes, has remained.

In its heyday, the buildings where cathouses operated weren’t obvious. Customers often would acquire lists with names and addresses at train stations and from concierges, so they would know where to look. Most people who bought such lists would quickly discard them, but a few have survived and are on view at the Museum of Sex.

“That’s how we know where a lot of the brothels were,” said Brenner. “It was the epicenter of New York City vice.”

Many brothels operated out of private residences in three or four-story, residential buildings that had once been lived in by wealthy families. One such former house of ill repute — since torn down — was located next door to where the Museum of Sex stands today. The museum is one of few links to the neighborhood’s naughty past with Le Trapeze, a famous swingers’ club that operated nearby on East 27th Street, having closed last December.

Some of other places of interest are still around, however, such as the Senton Hotel at 39 East 27th Street, once a notorious bachelors’ residence that still operates as a hotel. At one time, men stayed there with the singular purpose of having easy access to all the Tenderloin had to offer. Those venues were able to operate, in large part, because they paid protection money to the longtime local precinct commander, Inspector Alexander “Clubber” Williams. According to local lore, it was Williams who gave the area its nickname, once commenting after being assigned to the command, that he’d eaten chuck long enough and would be switching to tenderloin. Then there were other cops who looked the other way simply because they had an interest in taking part in the festivities, a fact that did not go unnoticed by Reverend Parkhurst.

Other kinds of crime were also rampant in the Tenderloin, which Oscar Wilde, who was in New York City for a book tour, once learned the hard way.

As Brenner tells it, Wilde encountered a handsome, young gentlemen who lured him to a gambling establishment, where the established writer promptly got very drunk and lost all his money. Realizing he’d been had, Wilde later went to the Financial District to cancel the three checks he’d written and to contact police. Later that evening, his checks were returned to him at his hotel room at the Gilsey House by none other than Williams himself, who apologized for the inconvenience.

“He didn’t want him writing about what a rip-off the Tenderloin was,” explained Brenner. As for the handsome, young gentleman who duped Wilde, Brenner suspects he probably met the same fate as most criminals encountered by the area’s top cop, which is to say he was likely beaten within an inch of his life with Clubber’s night stick.

The landmarked Gilsey House was once a hotel in the heart of the Tenderloin.

The Gilsey House, meanwhile, located at 29th Street and Broadway, is still standing. It’s now a pricey condominium building, but is there to stay thanks to being landmarked. It was built in the Second Empire architectural style, but was known better at the time it opened in 1871 for having a telephone in every room. Samuel Clemens stayed there as did Diamond Jim Brady, a wealthy financier and his actress lover Lillian Russell, who were both said to have insatiable appetites for food, drink and women.

Another remaining building at the southwest corner of 24th Street and Sixth Avenue, now home to the Corner Cafe, was once home to Koster & Bial, a music hall that was closed after being raided by police as an orgy was taking place. Koster & Bial was the strip club of its day with scantily clad dancers and private, back rooms to spend time with them in. Ironically, another strip club to operate at this address a full century later, Billy’s Topless, was closed after laws surrounding topless bars were actively enforced during the Giuliani era.

In the days when the el train rumbled overhead, Sixth Avenue was the height of the Tenderloin. Few reminders remain though, especially since the construction boom in the 1990s when the area was rezoned. The construction that’s been happening in the district at such a steady pace is was what prompted Brenner, a preservationist at heart, to start giving the tours in the first place.

The former Everard Bathhouse for men, which was open for nearly 100 years, despite a fatal fire

He would like to see plaques put on certain buildings that once had historical value (or the buildings there previously did). One of them is a former men’s bathhouse located at 28 West 28th Street, where several patrons died in a fire. The Everard Bathhouse, named after its founder, James Everard, who’d made his fortune in the brewery business, had actually become better known as “Ever Hard” due to its reputation as a cruising destination for gay men. It remained open for nearly a century from 1886 to 1984, finally closed by Mayor Ed Koch during the AIDS crisis.

Brenner said he would like to see a plaque that specifically honors the victims.

Then there was a block of brownstones on West 25th Street, that’s now entirely gone except for one and a section of another, that was once known as the home of “the seven sisters.” The sisters were likely not related, but this was the name given to seven neighboring, high-class brothels.

“You couldn’t just show up with a wad of cash,” said Brenner of the seven sisters. “They were by invitation only.”

“Satan’s Circus” tour leader Robert Brenner is also a neighborhood preservationist.

Men who visited were also expected to dress up in black tie and bring a bouquet of flowers for the woman they were there to see. A big event was a Christmas Eve party where all money that was earned went to benefit a local orphanage. The proprietors of these establishments were almost always women, usually former ladies of the night themselves. Men wouldn’t take over the sex industry as pimps until the Prohibition Era.

When the Tenderloin started to go on the decline, it was for a number of reasons, and it transitioned into the Flower District. This is in part because some brothels had been operating florist shops as a front, so when the red-light district shifted north towards Times Square, they went legit.

While some florists have remained, Brenner is certain that the current district identity will also be gone in a few years as smaller buildings get pushed out in favor of much larger, luxury towers and hotels.

Additionally, from 1895-1897, the Tenderloin faced serious opposition from Teddy Roosevelt, then New York City’s police commissioner. But his efforts to crack down on the sale of alcohol at saloons, making it legal only at restaurant hotels when the Raines Law was passed in 1896, was seen as being discriminatory to men who couldn’t afford to go to hotels. Roosevelt was let go from his post by the mayor, eventually moving on to become president of the United States.

The final nail in the coffin for the local sex industry, however, was the fatal shooting of famous architect Stanford White, a Tenderloin resident, in 1904 by Harry Thaw. Thaw was the unhinged and jealous husband of showgirl Evelyn Nesbit with whom White had an affair when she was just 16. After his death and the massive tabloid coverage that followed, rich men like White became wary of the red-light district.

More on the Tenderloin’s history and numerous other venues that once stood within its boundaries can be learned about on the “Satan’s Circus” tours that take place on Saturdays at noon. For tickets, $20, visit the Museum of Sex’s website.

For information on Brenner’s Manhattan neighborhood tours, visit his website.

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3 thoughts on “Flatiron’s red-light district past explored in historic walking tour

  1. Why does T&V constantly publish “news” concerning neighborhoods that are (at best) peripheral to Peter Cooper Village/Stuyvesant Town? Isn’t there enough going on here to fill the pages of this tenth-rate “newspaper?”

    Any update on the suicides earlier this year? Any more buckets of sulfuric acid on the property? What happened with that situation? Was it a meth factory, as many (if not most) of us suspect? T&V has to be the most inconsequential and non-newspaper in existence. There was a time when it actually reported news that was pertinent to the property, but that was way back. Who buys and reads this “newspaper” outside of PCVTA tenants? I’m pretty sure that the number of actual subscribers is down to the bone.

  2. Pingback: Highlights From Mayor de Blasio's Released Emails - The Briefly

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