Leonard "Lenny" DiMaria (b. 1941), is a New York mobster who became a Caporegime in the Gambino crime family and a close associate of alleged Gambino Boss, Nicholas "Little Nick" Corozzo. DiMaria has served as his right-hand-man for over 30 years.
In the early 1980s, DiMaria became a soldier in the Gambino family. In February 1986, DiMaria, along with John Gotti and other family figures were prosecuted for racketeering, but were all acquitted. It was around this time Gotti would appear in Time Magazine and became known as the "Teflon Don", because of all his acquittals. DiMaria operated loansharking and extortion operations in both Queens and Brooklyn in his early days, however, according to Jerry Capeci, DiMaria was never a 'tough guy' coming out of Brooklyn.
In 1991, on the basis of testimony from mob informant Salvatore "Sammy the Bull" Gravano, Gotti was convicted and sentenced to 100 years in prison. After the Gotti conviction, DiMaria was promoted to Caporegime and given his own crew in Queens. In 1994, his fellow captain and associate Nick Corozzo became a member of the Gambino family 'Ruling Panel', which was meant to run the family while John Gotti was in prison. DiMaria was now one of the main chiefs in the family, controlling everything from loansharking and illegal gambling, to racketeering and murder for hire. At age 53, DiMaria now had one of the best positions in the family, and soon began a lucrative partnership in Florida.In 1995, DiMaria, and Gambino capos Ralph Davino, Jr. and Anthony Ruggiano, Jr., together with Anthony "Tony Pep" Trentacosta, started operating in Florida on behalf of Corozzo, soon to be the sole Boss of the Gambino crime family. These three capos would be called the "South Florida Crew", operating from both New York and Florida. In June, 1996, DiMaria, Corozzo and six other Gambino associates, were arrested and prosecuted for racketeering charges. While out on bail, DiMaria was prosecuted a month later on separate loansharking and racketeering charges, only this time in New York, after a three year investigation by FBI. After six weeks in house arrest, DiMaria and Corozzo were sent to a federal lockup to await trials in New York and Florida.Both Lenny DiMaria and Corozzo pleaded guilty to the racketeering and loansharking charges, receiving an 8-10 year prison sentence, which DiMaria was to serve in Cumberland, Maryland.Released from prison in 2005, DiMaria at age 66 is still a Caporegime in the Gambino family, running racketeering and loansharking operations in Queens and Brooklyn. DiMaria is also allegedly running the entire South Florida faction for the alleged bosses Corozzo and John "Jackie Nose" D'Amico. DiMaria may even be an Underboss, or street boss, for Corozzo.
In February 2008 DiMaria was named as a defendant in the Operation Old Bridge indictments. His boss Nicholas "Little Nick" Corozzo, however, fled New York due to the massive indictments from Operation Old Bridge, acting on prior knowledge. On March 14, 2008, DiMaria was released from federal custody, possibly on bail.