Photos by Frank Mastropolo

Don’t let the shi shi galleries, bone broth bistros and man-cessory shops fool you. The country’s most violent criminals have lived and plied their trade in the East Village and Lower East Side for more than two centuries.

Of course, a man needs a place to relax after all that mayhem. Here is a current look at some of the most notorious gangsters haunts in the neighborhood, listed chronologically.

Click through the slideshow to see what our favorites look like today, then leave your own in the comments.

<strong>Bowery Boys Saloon Headquarters, 40 Bowery</strong>

Bowery Boys Saloon Headquarters, 40 Bowery

Pat Mathews’ Bowery Boys was one of the many nativist gangs in the Five Points during the mid-1800s. The gang’s headquarters was a saloon at 40 Bowery. On July 4, 1857, the Dead Rabbits, a rival Irish gang, assaulted a police officer in front of the bar. The Gangs of New York relates that when the officer took refuge inside, it touched off 48 hours of rioting between the gangs. It took the intervention of the National Guard to end the pitched battle. Today 40 Bowery is home to Ken’s Asian Taste restaurant.

<strong>Armory Hall, 158 Hester Street</strong>

Armory Hall, 158 Hester Street

Armory Hall was a popular hangout for criminals and prostitutes in the late 1870s. The saloon was owned by gangster Billy McGlory, a former member of the Forty Thieves and the Chichesters. At Armory Hall, “brawls and bloodshed were commonplace,” according to Incredible New York. “The incautious visitor who came there alone might be drugged, robbed, tossed into the street, and then stripped of all his clothing.” McGlory sold Armory Hall in 1889. Today a new building houses a mix of apartments and businesses.

<strong>Segal's Café, 76 Second Avenue</strong>

Segal's Café, 76 Second Avenue

Owned by wiseguys Louis “Little” Segal and Aaron “Big Aleck” Horlig, Segal’s Café was a favorite spot for gamblers, pickpockets, prostitutes and pimps. Enforcer “Dopey” Benny Fein and “Big” Jack Zelig, leader of the Monk Eastman gang, were regular customers. In 1912, Zelig received an anonymous phone call at Segal’s summoning him to 14th Street. The book Gangsters, Murderers & Weirdos of the Lower East Side notes that Zelig hopped on the Second Avenue trolley and was shot and killed by “Boston Red” Phil Davidson as the trolley passed 13th Street. Today the evangelical Second Avenue Church is on the site.

<strong>New Brighton Athletic Club, 57 Great Jones Street</strong>

New Brighton Athletic Club, 57 Great Jones Street

Paul Kelly, an Italian whose real name was Paolo Antonio Vaccarelli, was an ex-boxer and leader of the Five Points Gang. Kelly was a dapper gangster who wore silk ties and spoke five languages. In 1904, Kelly opened the New Brighton Athletic Club at 57 Great Jones, a place that staged bare-knuckle fights. Andy Warhol’s company bought the building in 1970 and leased it to artist Jean-Michel Basquiat, who died of a heroin overdose in the upstairs loft in 1988. Today it’s home to a high-end butcher shop, Japanese Premium Beef and the exclusive Bohemian restaurant.

<strong>Little Naples Café, 59 Great Jones Street</strong>

Little Naples Café, 59 Great Jones Street

Next door at 59 Great Jones was Kelly’s Little Naples Café, a saloon where mobsters like Chick Tricker and Louie “The Lump” Pioggi wined and dined. The two buildings were interconnected. Gunplay was always on the menu at the Little Naples. Infamous New York states that after a prolonged gun battle in 1905, police closed the Little Naples for good. Today 59 Great Jones has no retail frontage.

<strong>Chinese Theater, 5-7 Doyers Street</strong>

Chinese Theater, 5-7 Doyers Street

Beginning in 1893, the Chinese Theater presented operas and plays on winding Doyers Street in Chinatown. It was a time when the tongs, originally community associations, expanded into criminal activities like protection rackets, gambling and prostitution. On August 7, 1905 two rival tongs, the On Leongs and the Hip Sings, waged a wild gun battle inside the theater that left four people dead.

Taxi Dances and Vaudeville: Excavating Manhattan’s Lost Places of Leisure notes that the theater, which had become a popular tourist stop, suddenly earned the reputation as an unsafe place to visit. Ticket sales declined and the theater closed by the early 1910s. Today a mix of businesses, including a liquor store, share the buildings.

<strong>Arlington Hall, 19-23 St. Marks Place</strong>

Arlington Hall, 19-23 St. Marks Place

Jack Sirocco and “Dopey” Benny Fein were two mobsters on opposite sides of the labor rackets. Sirocco’s goons would protect management interests during labor strikes; Fein’s thugs worked for the unions. Sirocco, an Italian, booked community center Arlington Hall for a bash on January 9, 1914. As the East Village was largely controlled by Jewish gangsters at the time, there was bound to be trouble. Ephemeral New York states that before the affair started, Fein and his gang unleashed a volley of gunfire at Sirocco’s group outside the hall. Only one person was killed, an innocent passerby named Fredrick Strauss. Fein was arrested for murder but was released after informing on corrupt union officials. Arlington Hall has gone through many transformations that included the Dom nightclub and the Electric Circus. Today apartments and retail stores share the site.

<strong>Restaurant, 19 Second Avenue</strong>

Restaurant, 19 Second Avenue

Nathan Kaplan, known as Kid Dropper and John Weyler, aka Johnny Spanish, were two of the toughest Jewish gangsters in Paul Kelly’s Five Points gang. Their specialty was “labor slugging.” Companies would hire gangs of strikebreakers to attack union members; unions would also hire enforcers to recruit new members. The pair supplied muscle to both sides. After lengthy prison stays, the two men in 1918 violently competed for work in the labor rackets. The New York Daily News reported that on July 19, 1919 Dropper got word that Spanish was dining at a Second Avenue restaurant. As he left, Spanish was shot and killed by three men. Dropper was arrested but because of lack of evidence was never charged. Today TD Bank occupies most of Second Avenue between Houston and First Streets.

<strong>Black Bottom Nightclub, 66-68 East Fourth Street</strong>

Black Bottom Nightclub, 66-68 East Fourth Street

The Singapore Free Press in 1930 called the Black Bottom “a shabby little night club, used as a rendezvous by the toughest of the East Side underworld racketeers.” On October 31 that year, “Cowboy Larry” Viscardi and Charles Greco, criminals with long arrest records, entered the club shortly before closing. At least one man with a machine gun appeared in the doorway and opened fire as waiters and musicians hit the floor. Viscardi and Greco were killed but no one in the club would offer any clues about what happened. Today the building houses the Ellen Stewart Theater and Archives, part of the La Mama Theater Annex.

<strong>Umberto's Clam House, 129 Mulberry Street</strong>

Umberto's Clam House, 129 Mulberry Street

After mobster Joe Columbo was murdered at a Columbus Circle rally in 1971, Columbo family leaders believed “Crazy” Joe Gallo, once a member of the gang, was responsible. Gallo celebrated his 43rd birthday at the Copacabana on April 7, 1972, then returned to Little Italy around 5 a.m. Gallo, accompanied by his new wife, stepdaughter and bodyguard, stopped by Umberto’s Clam House before going home. Gunmen soon appeared at the restaurant and blasted away. Ephemeral New York relates that Gallo pulled out a revolver and returned fire but was hit five times. He staggered out to the street and later died. Umberto’s has moved twice since the incident. The restaurant today is at 132 Mulberry Street, a few doors from its original location. Da Gennaro, an Italian restaurant, now occupies the original site of Umberto’s.

<strong>Ravenite Social Club, 247 Mulberry Street</strong>

Ravenite Social Club, 247 Mulberry Street

In the late 1970s and ‘80s, the storefront at 247 Mulberry in Little Italy was used as the headquarters of the Gambino crime family. The club had two large rooms with tables and chairs. John Gotti, who ran the gang, presided over weekly meetings from a table in the rear room. The FBI secretly bugged the Ravenite and an apartment upstairs used by Gotti. FBI and New York City police raided the Ravenite on December 11, 1990. Gotti was arrested and convicted of five murders. The New York Daily News reported that in October 1997 the U.S. Marshal Service condemned the building and evicted its tenants. Today the Cydwoq shoe store occupies the space.