How a Home For the Homeless Became a Celebrity Crash Pad

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.

An ad for apartment 2W, at 295 East 8th Street, calls it “the most WOW loft you’ll ever see, fit for anyone with a flair for the spectacular.” Matt Dillon once lived in the massive brick building at the corner of Avenue B, across from Tompkins Square Park.

These days, you’ll need to plunk down $8,500 a month for the privilege of living in one of the Gothic building’s eight lofts. But it hasn’t always been this exclusive. All the opposite: at the turn of the 19th century, it helped to keep thousands of young boys off of New York’s overpopulated, dangerous city streets.

Jerry Senter, a broker at Corcoran Real Estate who represents apartment 2W, says “the history is sadly of little interest” to his clients, so he doesn’t discuss how the Tompkins Square Lodging House for Boys was the place where homeless youth went to be fed, washed, and transformed into well-rounded citizens.

The building itself was built in 1887, but the reason it exists dates back 34 years earlier, to 1853, with Charles Loring Brace—one of the fathers of modern philanthropy. On graduating from Yale in 1846, with degrees in divinity and theology, Brace began work as a minister on notorious Blackwell’s Island — the present day Roosevelt Island. In Emma Brace’s biography of her father, she describes his fascination with helping others: she said that his visits to Blackwell’s Island were the beginning of a “life for which his longing has been growing increasingly strong.”

One day, he decided that he needed to extend his calling to more directly addressing the needs of the many New York City children living in poverty at the time. In 1852, Charles wrote in a letter to his father — collected by his daughter, Emma, and included in his biography — that being a city pastor wouldn’t be enough: “I don’t care a straw for a city pastor’s place,” he wrote. “I want to raise up the outcast and homeless, to go down among those who have no friend or helper, and do for them what Christ has done for me.” In other words, Brace wanted to do something that had an immediate impact.

Tompkins Square, in the words of the Landmarks Preservation Commission, was a “nexus of civil disobedience” at the time (in that sense, the area hasn’t changed much). It was the site of the Astor Place Opera House Riot, and the “work-and-bread rallies” of 1857. As a hub for German immigrants, the population was even more dense than it is today. Tenements popped up after the grid system was established in 1811.

Poverty was rampant and the educational needs of the area’s children were not being met. Prisons of the day held vagrant children as well as adults, with no distinct reform centers yet established for juveniles. For Brace, it was too much to bear.

He took his philanthropy to the streets; he started the Children’s Aid Society and helped put into place the things that we take for granted: free kindergarten options, health care for children, “reading rooms,” and shelters, or lodging houses.

In 1853, he started the Orphan Train Movement. At first, Brace looked outside of New York for ways to place our homeless children; he sent them on trains up to New England and to other parts of the United States, offering them the chance to live with stable families and learn farming and other trades. The trains would take children from orphanages, broken homes, or the streets to other towns, where they would be interviewed and placed. It was one of the first examples in New York of “foster care.”

Brace continued his initiative inside New York City as well; in addition to the Orphan Train Movement (which continued into the early 1900s), he helped open America’s first industrial school and begin its first free lunch program. The first boy’s lodging house opened in 1854; several more opened across the Lower East Side, including the Tompkins Square Lodging House at 295 East 8th Street — the Children’s Aid Society keeps a clear collection of the societal goals and achievements on its website.

Calvert Vaux, of the Vaux and Radford Firm, designed the Tompkins Square House: that explains its Gothic pointed rooftops and medieval-looking structure — it looks almost as though several buildings were thrown together at the middle. Vaux was responsible for designing this house as well as the Elizabeth Home for Girls and the Sullivan Street Industrial School (both designed in 1891).

Vaux arranged the building so that, essentially, boys couldn’t enter it without being subject to cleaning. Harper’s Weekly reported in 1886 that in order to get inside, boys had to enter through the basement; stairs led down into a courtyard, which in turn led to an adjoining washroom that preceded the reception area. That way, before the boys were screened and housed, they would also be clean.

Yes, the building ran under the auspices of Brace’s Children’s Aid Society, which aimed to take children off of the streets, not just for shelter and safety but to turn them into productive members of society. That was the lodging house’s particular spin on outreach. In his , “The Best Method of Disposing of Our Pauper and Vagrant Children,” Brace noted the need for juvenile labor in the United States. In England, he said, there was a big problem with figuring out what to do with homeless youth. On the other hand, America is bursting with opportunity:

We have imitated their method of treatment without their reasons for it. We have crowded asylums and reformatories with young paupers and vagrants and petty criminals not yet inured in crime, when a far more effective and more natural treatment was ready to our hand.

Well, there it was! The solution to New York’s petty crime problem was simple: house the boys, teach the boys; put the boys to work.

That was what boys who went to the Tompkins Square Lodging House did; they ate, slept, learned, and went to work. The lodging houses ran primarily on donations to the Aid Society from the general public. appealing to keep the houses open, begging for contributions to provide food and loaned supplies for the children. After boys were accepted into a lodging house, they were expected to get jobs that allowed them to pay small rental fees for their accommodations and schooling.

Of course, the rental fee was small compared to what it is today. Though the lodging house was big, it wasn’t quite as roomy as it is now. Still, the boys were learning the value of money, paying for their beds and educations.

Brace’s plans seemed to be working; boys whom the home had sheltered grew up to be congressmen, politicians, and successful businessmen, according to Brace and the census record index of the Children’s Aid Society. Actual proof of what happened to each child, however, is harder to confirm.

It does make one wonder: were the boys happy with their arrangements? After all, the lodging houses and the Orphan Train Movement were, in some ways, a system that provided free labor. In some ways, that is a very peculiar and specific type of slavery.

I did, however, come across one letter from a young man named George Fink who wrote to the Children’s Aid Society in 1890 to give the organization an update after being sent to work at a farm.

Fink wrote: “I can say that I am as well satisfied as anybody would be. I can eat until I am satisfied, I drink cow’s milk all I want I go a hunting when I want to — there are plenty of opossums, rabbits, squirrels and birds…. I am satisfied with my home. I do not want to live in the city any more.”

It seems like even though the lodging houses provided temporary asylum for the young homeless, they weren’t as ideal a living situation as Brace thought. They were still very crowded, and didn’t actually take boys out of harmful situations. The fact remained that the boys still lived in the city, and sometimes, it was simply better for boys to get to work for free on a farm, if it meant that they got to attend school as well.

Still, at least for the time being, something was put in place in the city to remove the “vagrant children” from the streets.

The Newsboy’s Lodging House was where the funeral of Charles Brace took place on December 9, 1890. Emma Brace collected bits of his obituary from the New York Evening Post: “Those who had the privilege of knowing him,” it said, “will long remember his engaging personality, the chief light of which was the charm and grace of pure goodness.” Everywhere he went, it seemed, good karma followed.

It makes sense, then, that philanthropy continued at the Lodging House, even after the Children’s Aid Society sold the property to Darchei Noam in 1925, and the address became a Jewish center in 1928.  

That explains the inscription across the entrance of the building: “Talmud Torah Durch Moam.”

For the next years, 295 East 8th Street would be home to a Jewish school, offering classes for immigrants, and then in 1950, a charity center for the poor, accepting donations of food and clothing. Up until 1970, the building was a fully formed center for Jewish culture and charity. This all came to a halt in 1974, when parents of children who used the center became increasingly fearful as the neighborhood took on its ‘70s mantle of drug use and vandalism with the park across the street as its epicenter. The East Side Hebrew Institute abandoned the building.

Then a miracle of sorts came about in 1978 — Roland Legiardi-Laura, a filmmaker and poet, . He made some renovations, deciding to keep Vaux’s original design ideas but restore the building, and in 2003 it became the expensive luxury apartment building we know it as today.

Finally — we get the origins. But how was the decision made for the apartment building to be landmarked?

Quite easily, in fact–and pretty quickly. In 2000, the Landmarks Preservation Commission generated a report calling for landmark status for this former Children’s Aid Society facility. The public hearing was held in February 8, 2000, and the commission received 25 letters of support, including one from the Lower East Side Tenement Museum.

It was an easy argument—the building was among the only standing lodging houses and industrial schools left in the Lower East Side that still maintained its original design. On top of that was its Calvert Vaux touch. It represented new opportunities for young boys, and the start of a foster program for young children. The Children’s Aid Society deserved recognition, as did Mr. Brace.

There wasn’t much dispute.

And, there it is; the entire building has moved up. The young boys that lived there initially went on to better, more fruitful lives, at least in the Children’s Aid Society’s reckoning. The Jewish center provided more education for immigrants, along with food and clothing for the homeless. The building was a gem in an otherwise chaotic, poor, restless population.

And it still is a gem today, especially for New York’s top realty sharks, even though from the outside, the building actually isn’t all that appealing. The pointed tops and arched windows make it look like it was plopped out of some ancient European town and left to stand until it crumbles. The apartments are dark despite the glass door entrance and many “oversized windows.”

The nicest part of the building from its outside is its commanding height, and how out of place it appears on the corner of 8th and Avenue B, in the middle of the East Village, where the only buildings that aren’t tiny are the ones that serve other purposes—schools and stores.

The layout of each apartment, however, is open plan, with very few walls. Key features? Exposed brick, the aforementioned oversized windows, modern hardwood floors, renovated bathrooms, and pre-war detail. “There are very few other amenities,” Senter said, “but it’s worth it because of the space.”

“Worth it,” in this case, means worth $8,500 a month. Let’s just say upwardly mobile homeless youth in search of a lodging house need not apply. Current residents seem to be a mix of trendy newcomers, students, and wealthy families, looking out over Tompkins Square Park at the very poor.