Born in New York City, DiLeonardo grew up in Bensonhurst, Brooklyn. He lived there until 1998, when he moved to Eltingville, Staten Island. At age 10, DiLeonardo was scarred on the face by a dog attack, resulting in the nickname "Mikey Scars". His parents were second-generation immigrants, his father's parents immigrants from Bisacquino, Sicily. His mother was a seamstress and his father was a professional bowler. DiLeonardo had two brothers; Colombo crime family mobster Robert DiLeonardo (who was murdered July 16, 1981 on orders of Cosa Nostra, thus Michael could not retaliate and James (Giovanni) DiLeonardo. DiLeonardo's grandfather, Vincenzo DiLeonardo, was a captain in the Brooklyn faction run by Salvatore D'Aquila who was the boss of bosses at that time.. As a young boy, DiLeonardo met Gambino boss Carlo Gambino several times at his grandfather's house. DiLeonardo started running with violent street gangs as a teenager.
In 1973, DiLeonardo graduated from New Utrecht High School in Brooklyn. He attended college for eighteen months, but did not graduate. In 1985, at age 29, DiLeonardo married Antoinette "Toni" Marie Fappiano, a cousin of Gambino underboss Frank DeCicco. DiLeonardo had one son with Fappiano, Michael DiLeonardo, Jr. After twelve years of marriage, DiLeonardo started an affair with Madeline Fischetti. He kept Madeline in a rented apartment in Bay Ridge, Brooklyn while maintaining a home with his wife and son on Staten Island. DiLeonardo eventually divorced Antoinette and married Madelaine; they have a son Anthony.
A wealthy man, DiLeonardo owned a mansion on Staten Island overlooking Raritan Bay.
By age 21, DiLeonardo had started working for the Gambino family. Since the 1960s, he had been running errands for tips from several Gambino associates. They would give him money for his pocket, he would do things like vandalize and assaults for them. DiLeonardo frequently visited the Veterans and Friends social club in Brooklyn run by boss Paul Castellano. However, DiLeonardo considered capo Paul Zaccaria and Jerry D'aquila to be his mentors in the family.[2]
In 1980, DiLeonardo opened a social club a block away from the Veterans' Club. In early 1981, he moved the club to a different location in Brooklyn. A successful venture, the club's customers included Gambino soldiers Salvatore "Sammy the Bull" Gravano and Frank DeCicco. DiLeonardo also used his club as a headquarters for his bookmaking and loansharking, gambling operations. He was successful and then went into a business venture and became partners in a produce market with Peter Castellano, cousin to Paul Castellano. During the mid 1980s, DiLeonardo became a close friend of John A. Gotti, commonly known as "Junior", who was the son of future boss John J. Gotti. Junior Gotti eventually named DiLeonardo as godfather for his second son.
On July 16, 1981, DiLeonardo's brother Robert was killed in a mob-related shooting. DiLeonardo wanted to kill the shooter, but boss Castellano ordered him to stay out because it was related to internal Colombo business.[2] In the 1980s, DiLeonardo maintained so-called legitimate jobs as a shop foreman for teamsters local 282. DiLeonardo soon opened his own construction company, Metropolitan Stone, with Edward Garofalo, Gravano's brother-in-law.
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