The two drug cases, however, were far from LoPiccolo's first involvement in heroin trafficking. Press coverage at the time made a point of noting that he had previously served 9 years out of a 20-year Federal sentence in Leavenworth for a 1958 narcotics conviction in New York. LoPiccolo, listed as living at 233 E 69th St on the Upper East Side of Manhattan at the time, had been convicted as a "ringleader" of a heroin operation alleged to have attempted to distribute ~38 lbs of heroin imported from France; among the 16 other defendants charged in that case included men with addresses in Long Island, Queens, the Bronx, NJ, and Philly, with the heroin alleged to have been supplied by Philly member Peter Casella and Gambino member Vincent Todaro. While a number of sources have stated that Chicago's LoPiccolo was identical to the Joseph LoPiccolo who was identified as a Gambino member in 1963 by Joe Valachi, I believe that this is likely erroneous, and the figure named by Valachi was more likely an unrelated Giuseppe LoPiccolo of Partinico by way of Detroit. Further, in 1958, an FBI file notes that LoPiccolo's notebook where he recorded narcotics transactions had been recovered in the 1958 bust, with an entry apparently described a transaction "to Santo: Cuba and U.S.", which investigators believed indicated that LoPiccolo was supplying Santo Trafficante, Jr. This seems to have been the source of the highly unlikely scenario claimed on several internet accounts that Joseph LoPiccolo from Chicago was both a Gambino member and a capo in the Tampa family. Around the time of his 1958 bust, LoPiccolo was alleged to have had addresses in both NYC and Miami.
Joseph Paul LoPiccolo was born April 28th 1918 in Chicago to Filippo Lo Piccolo of Monreale and Margherita Viso of Altavilla Milicia, who had married in Chicago the previous year. The 1978 Tribune article noted that LoPiccolo was the son of a Chicago butcher, and the 1930 census confirms that Filippo Lo Piccolo worked as a butcher. The LoPiccolos lived in the Little Sicily neighborhood on the Near Northside of Chicago, an area with a high level of serious mafia activity. Filippo was possibly a relative of D'Aquila-era Gambino capodecina Stefano LoPiccolo, also from Monreale. Bill Feather has asserted that they were brothers, but this doesn't seem likely. Stefano LoPiccolo emigrated to New Orleans in 1905, listing a brother named Filippo already residing there as his contact; further, on his WW1 draft card in Brooklyn, Stefano stated that his brother "Phillip" LoPiccolo lived in Brooklyn as well. Chicago's Filippo LoPiccolo arrived from Monreale to NYC in 1912, however, bound for Chicago. Given the shared given name Filippo in both families, it's possible that they were cousins. Margherita Viso arrived in Boston in 1909. As has been detailed in other threads, Margherita's hometown of Altavilla Milicia has a very long and closely intertwined history with Chicago, with a number of Milicioti over the years connected to the mafia in Chicago. Filippo LoPiccolo died in Chicago in 1958 (the same year that Joseph was busted for heroin trafficking), while Margherita died in suburban Elmhurst in 1973.
Joseph Paul LoPiccolo married Caroline Riggio in Chicago in 1942. Caroline had been born in Kansas to a family from Chiusa Sclafani who subsequently relocated to Chicago's Little Sicily (Chiusa Sclafani is another town connected to the mafia in both Chicago and Kansas City). That the couple remained in Chicago, rather than relocating to New York, is supported by the fact they had several children born in Chicago in the 1940s and 50s. Joseph P. LoPiccolo's 1958 address in NYC was on E 69th St, suggesting a transient residence rather than a guy relocating with his family, and all of their children attended high school in the Chicago area. There are several records in the 1950s for flights to and from Europe/NYC for a Joseph or Joseph P. LoPiccolo, including a 1956 flight with a "Margaret LoPiccolo", almost certainly Joseph's mother Margherite Viso. While several online accounts state that LoPiccolo served a 20-year sentence for his 1958 conviction, as noted above, he only served 9 years, at which point he likely returned to Chicago.
In December 1972, the Chicago Daily News reported that Northside capodecina Ross Prio (born Rosario Fabricini in Ciminna) and upper-echelon Jewish outfit associate Lenny Patrick were subpoenaed to appear before a special Federal grand jury convened in Chicago to investigate "crime syndicate involvement in the narcotics trade"; Prio was soon off the hook, as he died later that same month. Joseph LoPiccolo was also compelled to testify at the grand jury by being given immunity from prosecution; when he refused, LoPiccolo was jailed for contempt of court in the Cook County jail for a year or two. In 1974, the Tribune reported that "dope peddler" LoPiccolo was a close friend of Chicago member Mario DeStefano (brother of the notorious Sam DeStefano), who was reportedly bringing in home-cooked spaghetti dinners for LoPiccolo at the County. At this time, LoPiccolo was stated to be residing in North suburban Skokie, which matches other information that I have for his children. In May 1977, the Tribune reported that LoPiccolo, "regarded by law enforcement officials as the city's top crime-syndicate narcotics figure" had vanished while under surveillance in Chicago by federal narcotics agents in December 1976. His room at the Hotel Belmont (unclear whether he had separated from his wife or if he was just using these hotels as "business" addresses), which had an 18-month lease left, had been neatly abandoned with no word to the hotel. The Tribune described LoPiccolo as "shadowy" and "mysterious", quoting one "veteran investigator" as stating that LoPiccolo "is the lowest profile guy we've ever seen. Almost nondescript", and drove a 1971 Pontiac. While the DEA suspected that LoPiccolo had either been whacked or had possibly fled to NYC to work with "Mafia boss Carmine Galante's drug-oriented rackets", we know that he was apparently still kicking around Chicago plying his trade. Following his subsequent heroin busts, Joseph P. LoPiccolo seems to have faded into obscurity -- or at least, he no longer appears in the papers in relation to the narcotics trade. He died in North suburban Lake Zurich in 1999.
Another claim made in internet accounts of LoPiccolo is that he was stabbed to death in a Staten Island cemetery in May 1978. This is patently false -- as noted above, Joseph P. LoPiccolo was alive and incarcerated in Leavenworth as of September 1978. Further, the Joseph LoPiccolo who was brutally stabbed to death in St. Mary's Cemetery in Grasmere, SI, in May 1978 was a 21-year-old kid who lived with his parents in Sheepshead Bay, BK. So, whoever the Joseph LoPiccolo who was claimed to be a Gambino member in 1963 actually was, it certainly wasn't this guy.
On the subject of the Joseph LoPiccolo identified by Valachi, Bill Feather argues that he was a Giuseppe Lo Piccolo who was born in Partinico in 1899, immigrated to Detroit in 1923, and subsequently relocated to Nassau County, LI, in the late 40s. This is consistent with several documents I've reviewed, including Giuseppe LoPiccolo's 1923 passenger manifest, his 1944 naturalization in Detroit, and a December 1968 death record for a Joseph LoPiccolo, born 1899/08/06, like the guy in Detroit, who was living in Great Neck and had his social security number issued in New York state in the early 1950s. I agree with Feather that, compared to Joseph P. LoPiccolo of Chicago, this guy is a much stronger bet as the Gambino member identified by Valachi. Some online accounts claim that the Long Island Piccolo was involved in drug trafficking with Paul Gambino, though I have no idea if that is true. Also worth noting that among the guys busted with Chicago's LoPiccolo in 1958 were the Gambino-affiliated father-and-son team Lorenzo and Ignazio Orlando of Elmont, Nassau County (Lorenzo seems to have been born in 1901 in New Orleans and made frequent trips over the years to Europe, consistent with a guy heavily involved in narcotics smuggling), so if both LoPiccolos were involved in narcotics, for all I know they both could have been linked to the Orlandos.
Given that he doesn't seem to have ever lived in NYC for an extended period, I doubt that Chicago's Joseph Paul LoPiccolo was a Gambino member. Was he a Chicago member? Possibly, can't be ruled out. While he was never identified as such, lists of Chicago's membership in those decades are fraught, as they included guys who weren't members and presumably missed some number of members who in fact were. We may never know. Given the men that he was busted with in 1958, however, he was clearly closely linked to guys with both the Philly and Gambino families who were heavily involved in narcotics. My suspicion is that he was actively involved in supplying heroin to Chicago for years. We already know that in 1952, Frank Pasqua, a Bronx-based Gambino member, was busted for supplying Chicago with heroin and was working with guys associated with the Chinatown crew (then under capodecina Bruno Roti) -- several of them, like the DiCaro brothers and Jimmy Cordovano (who was inducted into the Chicago mafia sometime in the late 50s/early 60s), continued their involvement in narcotics through the 50s and 60s. Pasqua was additionally cited in testimony before Congress as a narcotics trafficking partner of Jimmy Massi, also a Bronx-based Gambino member, who was in turn one of the men busted in 1958 along with Joseph P. LoPiccolo. Whether he was a mafia member or a longtime associate with close connections to both families (as well as, probably, Tampa and Detroit), LoPiccolo was likely a major cog in the NYC to Chicago heroin networks across the period that he was active.
As noted above, Joseph P. LoPiccolo's mother was from Altavilla Milicia, a town with a long and deep connection to both the mafia and Chicago. In the 1980s, Luigi Ronsisvalle testified that he was responsible for ferrying over 300 kilos of pure heroin to Chicago in 1977 and 1978 (valued by the Feds at the time as ~$1 billion in street value) for a major trafficking operation under Toto Catalano (directed by Carmine Galante's godson, Felice Puma). One of Ronsivalle's Sicilian contacts in Chicago was a man named "Frank Lombardo", who Ronsisvalle testified told him that he had personal ties to Paul Gambino. On the Chicago "zips" thread, I argue that this Frank Lombardo was very likely a Francesco "Frank" Lombardo who immigrated to Chicago from Altavilla Milicia along with many of his peasani in the 1950s - 80s and owned a pizzeria on the city's Northwest side; Lombardo had connections to local outfit figures and his extended family from Altavilla, who own numerous restaurants and catering companies in Chicagoland, have had a long history of criminal activity. Given the apparent connections to both the Gambino family and the Chicago family and shared Milicioto ancestry, one wonders if LoPiccolo had any connections to Lombardo and other recently arrived paesani in Chicago. Another Sicilian heroin trafficking figure in Chicago during this general period with ties to both Chicago and NYC, Francesco "Frank" Rappa (from Borgetto), was also reputed to have had ties to the Gambino family during the years that he had relocated from Chicago to Queens (and then subsequently returning to Chicago, like LoPiccolo).
A photo of Joseph Paul LoPiccolo, published in the Tribune in 1978 following his narcotics indictment that year:
