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The feel of an early 20th-century Italian immigrant hangout is evident after noticing DeRobertis’ Pasticceria’s original tiled floors and patterned tin ceilings. But the sweetness of its cannoli cream belies its historical connections to notorious crime bosses, rumored to have run operations from its back room over cups of espresso.

Credit: Greenwich Village Historical Preservation Society

Caffe Pugliese was a bakery opened by Paolo DeRobertis in 1904. His family lived in the neighborhood on East 11th Street and owns the building occupied by the bakery. Paolo handed the business over to his son, Robert, in 1928 and it was renamed DeRobertis’ Pastry Shoppe.

Although most people associate Manhattan’s Little Italy as the center of Italian crime, the East Village was home to many mafia members. Charlie “Lucky” Luciano grew up in the neighborhood on East 10th Street after immigrating from Sicily.

Luciano grew up in this building on 265 East 10th Street.

Born as Salvatore Lucania, Luciano was a tough bully who would extort aka offer “protection” to classmates for a penny a day at P.S. 19, then on Fourteenth Street. One of those kids was Meyer Lansky, who stood up to him, won his respect, and ultimately began collaborating together, often holding meetings in the back room of De Robertis’ Pastry Shoppe.

Lucky Luciano in 1936.

Meyer Lansky in 1958.

Salvatore Lucania changed his name to Charles Luciano after his illegal activities brought shame to his family. He avoided being drafted during World War I by intentionally catching chlamydia. During the Prohibition era, Luciano ran a large bootlegging venture which brought in over $100,000 a year. By that time, he was ascending mafia ranks but growing impatient with his partner, Joe “The Boss” Masseria, who wanted to exclusively deal with Sicilians; some did not want to work with Luciano’s friend, Frank Costello, because he was a “dirty Calabrian”.

Present-day KGB Bar on East 4th Street was originally the Palm Casino, a bar owned by Lucky Luciano. Credit: B.A. Van Sise for ontheinside.info

Luciano was nicknamed “Lucky” after surviving a near-fatal stabbing by Masseria’s arch rival, Salvatore Maranzano. By that time, Luciano had considerable power and actually ordered a hit on his partner Masseria by Maranzano (yes, the same man who just tried to kill him–how he finagled that, I don’t know!). Luciano did whatever Maranzano wanted in exchange for establishing Luciano as his right-hand man, but like in all mafia relationships, this one turned sour when good friend Meyer Lansky informed Luciano that Maranzano was planning to have him killed, too. Lansky brought together a hit squad posing as federal agents and stormed Maranzano’s office.

The bloody aftermath of Maranzano’s murder, 1930.

Luciano was now the boss of the most powerful crime family in America and Meyer Lansky was known as one of his most trusted friends. TIME magazine named Luciano one of the top 20 influential titans of the 20th century. He was eventually indicted by New York prosecutor Thomas Dewey for extortion and leading a prostitution ring. In 1946, his sentence was commuted and he was deported to Italy. Shortly after, Luciano secretly moved to Cuba. When the US government caught wind of Luciano’s resumed operations, he was deported again to Naples, where he died of a heart attack in 1962. Luciano often expressed homesickness for the United States and said to a reporter, “I’m a city boy. Italy’s dead–nice, but dead. I like movement. Business opportunities here are no good. All small-time stuff”.

Luciano being escorted by NYPD after his 1936 indictment. Note the sharp-looking jackets and fedoras.

Lucky was not the only mob figure associated with DeRobertis’ Pastry Shoppe. John “Handsome Jack” Giordano, a capo for the Gambino family was rumored to have conducted a bookmaking business in the pastry shop during the late 80s. John DeRobertis claimed to “have never heard of this gentleman”. In 2003, Enrico “Red Hot” Gentile, known for allegedly shooting a Genovese hitman, died of a heart attack on First Avenue shortly after leaving DeRobertis’. Annie and John DeRobertis, Jr., both grandchildren of Paolo, currently work in the shop. Their other grandfather, Michael, started Lanza’s Restaurant down the block.

While DeRobertis’ seems to downplay their storied connections to mafia history, the Old-World atmosphere and lack of touristy crowds deserves attention. One wonders what plans have been clandestinely calculated in the back room. People today can watch recent episodes of Boardwalk Empire, but at DeRobertis’ you can nibble on the same pignoli cookies that were enjoyed by Lucky Luciano and Meyer Lansky, whose spirits surely keep watch over this long-time Italian institution.