Orlando Michael Napolitano – aka “Mickey Naples” – was born on August 3, 1916, in Brooklyn, NY. He was one of twelve children born to Joseph and Lena (nee’ Grimaldi) Napolitano. His siblings were named Pasquale, Frank, Larry, Ernest, Anthony, Jean, Mary, Yolanda, Melphis, Gilda, and Rita. The Napolitano children were all raised in Kings County where they attended New York City Schools.
While he was still a young man, his parents relocated their large brood up to the State of Maine, settling into the City of Portland. This is the place where he and his family would remain for the rest of their lives. It’s also the city from where Mickey would operate his criminal rackets and schemes.
As a young man, Orlando Napolitano served as a sailor in the U.S. Navy and fought the Japanese in the Philippine Islands during World War II. After returning home from the war, he first went to work as a steamfitter for Local #217. He soon met and fell in love with a young local woman named Ernestine (Elizabeth) Tingley. The young couple got married around 1940 and took up residence within the area. They eventually had four sons together, Joseph “Little Joe,” who would later grow up to join his father in the criminal underworld; Robert M., who would grow up to become a lawyer; Pasquale L.; and Edward R.
Over the years, Mickey, Elizabeth, and the boys lived at various addresses around Maine. During the 1950s, the Napolitanos resided at 84 Beckett Street. By the early 1960s, they had relocated to another home on Mayer Road. Around 1965, the Napolitano family finally moved into 208 Eastern Promenade in Portland, which was a quaint two-story house with a large porch that would become their family’s compound for many years to come.
By the early 1970s, Mickey had another home on Lynn Fells Parkway in Melrose. He later relocated down to Pompano Beach, Florida on a seasonal basis. Yet, the Eastern Promenade house remained the primary Napolitano household until his death.