Tucked under the canopies of hedge funds, law firms, and expense-account lunch spots is an unusually character-driven block of East Midtown. In fact, this is probably the closest you’ll get to the East Village above 34th Street.

The Ramones sang about the scuzziness of 53rd and 3rd in the mid 1970s. And around that time, Village Voice journalist Arthur Bell profiled a hustler named Eddie who worked the corners here in 1972:

Eddie hasn’t seen sunlight in weeks. At 6 p.m. he gets up, drinks a glass of tomato juice, has a couple of eggs if his wife is around to scramble them, then usually goes to a 42nd Street movie. He liked “Shaft” and “House of Wax.” He seldom hustles 42nd. By midnight, he’s at Third and 53rd.

Of course today the corner is governed by the immutable laws of real estate and balance sheets. But there remain old tenements, a wildly diverse restaurant row, cozy bars and restaurants tucked under the stairs, and a little bit of jazz and salvation, if you’re patient.

So, If you think you can, well, come on man.

Street view here.

I guess there was a sale at the head store because this classic brick tenement has at least 31 decorative faces on it, though that’s probably an undercount. But say a little prayer for a couple of them that appeared to be losing the battle against the ivy creeping ever higher.

The steps hide a cozy Japanese jazz club called Tomi Jazz that saw an explosion of post-Covid interest leading to long lines. Here’s a video someone made, so you don’t have to stand waiting.

In fact, there are several bars and restaurants here that serve Japanese businessmen who arrived here in the 1980s, according to the New York Times. The diplomatic and Japanese cultural organizations in the area didn’t hurt, either.

The Lipstick Building at the corner of Third Avenue is one of the best-known post-modern office towers in these parts. Architects John Burgee and Philip Johnson addressed a setback requirement by shaping the building into three tapering elliptical tiers banded by red Imperial granite and stainless steel, decreasing in size as they rise.

The building has seen many tenants, but one left the building with notoriety.

On December 10, 2008 the S&P 500 was down an astounding 44% from its peak about 14 months earlier. Nevertheless, that morning a financier here sat at his desk to write $173 million in bonus checks, prompting his sons—also on the firm’s payroll—to confront him over the strange move.

These were good questions. The firm, Bernard L. Madoff Securities—obviously—was out of money. Later that day, he’d confess this to his family. This, of course, would go on to become a $65 billion Ponzi scheme, the largest such fraud in American history.

The firm occupied three floors here. The trading floor was on the 19th floor, and the computers and paperwork took up the 18th floor, according to the New York Times. These offices were modern, airy, and clean.

But the 17th floor was home to the “cage” where wire transfers went in and out and where the fraud was really perpetuated, according to a series in Vanity Fair. There was an outdated IBM computer server named House 17, encased in glass and loaded with software to generate fake money-making trades for investor statements.

Computer printouts and stacks of papers littered the floors and desks, ABC News reported at the time. "It looked like your crazy aunt's basement," a former tech manager told the reporter.

Almost 20 years later, the Lipstick Building is unfairly tied to Madoff’s fraud. The building itself faced its own hardships, both from the bad publicity and from the broader recession.

"Some people may see a stigma associated with it," a building manager told reporters on a leasing tour of Madoff’s space the year after the implosion. "But he's out of there. His bad karma has gone with him. ... Space is space."

Today the 17th floor is occupied by a high-end law firm.

Artist Jill Gill painted a watercolor of the Third Avenue side of the block in 1981, shortly before it was demolished.

This high-rise is sort of a geometrical masterclass in maximizing corner offices, zoning, and real estate. One account says this has 14 sides — most buildings just have four!

What’s now an open plaza on the corner of Third and 53rd was, for years, occupied by four tenements, the most notorious of which was a liquor store that reportedly asked for more than $20 million to leave before the end of its lease, according to the New York Times. By the time the developer reached an agreement to demolish the holdovers in 1990, the economics of the planned enclosed shopping center changed, and it was left as an open-air plaza instead.

On a sunny day, from some angles, this building even looks a little ok.

Today it’s home to big players in law and finance, such as Cerberus Capital.

Aside from the plaza outside, there’s an expansive privately owned public space inside taking the form of a sleepy three-story white atrium with a subway entrance and a hidden sushi restaurant. On one visit a guy was playing a piano in the basement while security eyed the premises. The basement, inexplicably, has an art studio. Hey, space is space.

This Beaux-Arts 6-story walkup has some nice white detailing. From 1922 through 1948 (and maybe even longer) this was occupied by the Girls Friendly Society Lodge, a philanthropic group dedicated to providing opportunities for young single women, according to a city zoning document. The Lodge is no longer at this location, but it still exists.

In recent years, this building has been used as a men’s shelter. As the number of New Yorkers needing shelter has grown, the needs of the population have become more complex. City Limits wrote in 2019 about one resident who required an oxygen tank—which was disallowed by the shelter’s fire-safety rules—who was effectively barred from the shelter, until a Legal Aid Society lawyer intervened.

There was a stabbing here 10 years ago, but the shelter has stayed out of the public eye since.

Three buildings for the price of one. These old rowhouses have finally been united under the same not-so-nice facade treatment.

Now I know everyone here is waiting for me to dive into the elephant in the room, so here we go: Yes, here is where, in 1962, the Oxford University Tiddlywinks Society bested the home team here, 23-5, according to, uh, tiddlywinks.org.

The college “winkers” were on a tour of the United States and soundly crushed the team of four “Madison Avenue public relations executives” who named their team the Cin Cin Irregulars, after the Italian restaurant here at the time. (I didn’t catch this episode of Mad Men.) After taking the Parker Golden Squidger Prize, the boys from Oxford absolutely pummeled every American team they played against.¹

Ok, fine, none of us know about tiddlywinks. It apparently involves using big discs to flip chips into a target in the center and had a burst of popularity in English colleges after World War II.

But since we’re talking flipping, we’ll talk about Peter Sudarsky, a former reporter-turned-corporate executive. “After directing his first film, A Child is A Wild Young Thing, he moved to New York to pursue real estate and vaccine development, swimsuit design and ping-pong,” according to his 2018 obituary.

In the mid-1980s, he bought these three buildings with the intention of springboarding their air rights toward building a 17-story apartment a block to the south. To make the deal work, he merged the lots into one, which unfortunately triggered a right of first refusal from the MTA, which was eyeing this space for an underground passageway for the unbuilt Second Avenue Subway, according to a court document.

In 1987, the MTA ultimately said it didn’t need the space, but it wasn’t so simple. “The community board and the City Planning Department asked transit officials to think harder about their decision,” the New York Times writes. “On the second to last day that the agency had to act, it changed its mind and said it did indeed want an easement.”

With the building permits on hold because of the easement, the city then down-zoned the area to a limit of eight stories, throttling Sudarsky’s dream. (This seems to have been part of a broader city plan to limit heights on side streets while allowing larger buildings on the avenues.)

Of course, he sued. But by 1988, his lenders forced Sudarsky to unload the buildings and the original tower site on East 52nd Street eventually became the Hungarian Consulate, according to the Times. And after years of litigation he lost the case, his investment, and his other properties. The rowhouses are still here.

When the New York Times caught up with him in 1999, it marveled at the limited scope of his holdings: a tiny piece of land between these rowhouses and the consulate:

“It measures all of 10 feet by 20 feet and contains nothing but a maple tree. It lies between the Hungarian Consulate and Bunchberries restaurant on East 53d Street. Mr. Sudarsky can't really get at it unless he crawls through the back window of Bunchberries. Some day, who knows, he could develop a treehouse there.”

If your sky-high hopes and plans have brought you back down to Earth, there’s plenty of salvation. In fact, there’s an unusual concentration of New Age and Eastern religious centers here. Toward Third Avenue, the Manhattan Sikh Center is being renovated to provide a place of worship with a prayer room, classrooms, and a place for visitors to get vegetarian food served by those “with prayer on their lips and humility in their hearts.”

The New Agey Seicho-No-Ie has its New York center in this strange converted townhouse. I spent some time on their website and still don’t get it, but interestingly, it started in Japan in 1930 and seems to be more popular in Brazil than its home country, these days.

The building was previously a social welfare mission that operated a well-loved day care center, according to Daytonian in Manhattan.

And then there’s the New York Theosophical Society, which embraces it all. It has its roots in Madame Blavatsky, who emigrated from Russia and quickly gained a following. She could probably have its own long entry, but we’ll save it for now.

The society opened in 1952 with a location that was specifically walking distance to the United Nations complex and bought the building next door in 1976, the society’s president wrote. The society hosts events—anything from Tarot readings, Reiki, Tea & Theosophy, and meditation circles—as well as a lending library.

It also operates the Quest Bookshop, a basement shop offering books on spirituality and anything metaphysical. This is your place if you want to brush up on Tarot, astrology, Kabbalah, palmistry, or anything else that helps give your spirit a little lift.

So, I’m sure there’s a lot here that I missed but just don’t know it. And I didn’t come here on a summer evening which, by the looks of it, probably opens up entirely new doors.

What’s Good: Not many places in this part of town you can find hidden bars and restaurants nestled under the stairs.

What’s Not: Not necessarily bad but the block has no overriding aesthetic: it’s a jumble of old tenements, Midtown high-rises, an apartment building that landed from 1960s Miami, and some townhouses in varying states of disrepair.

Block Rating: 7/10

Remember, if you like what you see here, smash that like and subscribe button.