The state of Connecticut has always been open mob territory, “no man’s land,” meaning it doesn’t belong to one single crime family. Several different mafia syndicates from all along the East Coast have had a presence in the state for decades, including the Genovese (NY), the Colombos (NY), the Gambinos (NY), the DeCalvacantes (NJ) and the Patriarcas (MASS-RI). And with mob activity, inevitably comes violence.

Below is a ranking of the most significant gangland slayings in the history of Connecticut:

Mafia Hit List – The Top 15 Connecticut Mob Murders of All-Time

1 William (Billy the Wild Man) Grasso: June 3, 1989 – The maniacal, hair-triggered 62-year old New England mafia underboss was shot to death as he sat in the front passenger’s seat of a van driving on Interstate 91 towards Worcester and dumped onto the banks of the Connecticut River in Whethersfield. His murder was part of a power play staged by the Boston faction of the Patriarca crime family and set off a half-decade of unrest in the borgata resulting in another dozen gangland hits. Grasso, gruff and rough around the edges, rose rapidly through the ranks of the Patriarca clan after developing a close friendship with Providence Godfather Raymond Patriarca, the mob family’s namesake, in prison.

2 Salvatore (Midgie) Annunziato: June 19, 1979 – The notoriously ruthless pint-sized mob captain in charge of rackets in Connecticut for the Genovese crime family disappeared from his East Haven home after getting into a car with his driver Tommy Vastano to go to a meeting with Billy Grasso. Annunziato, 59, had been running Genovese affairs in Connecticut since the 1950s and was alleged to have robbed a series of Grasso’s backdoor gambling dens in the months preceding his demise.

3 Ralph Mele: March 21, 1951 – One of the first true mob powerhouses to work exclusively in Connecticut, the greedy Genovese crime family captain based in New Haven was found shot to death on the side of the road in East Rock Park. He had been out drinking with Midgie Annunziato the night he was slain at Lip’s Bar & Grill and informants told the FBI that Annunziato clipped Mele and was “made” into the Genovese family shortly thereafter, given Mele’s territory, as reward.

4 Ralph (Whitey) Tropiano: April 3, 1980 – The Colombo crime family’s longtime capo in Connecticut was gunned down by a pair of masked assailants walking on a Brooklyn sidewalk. Tropiano, 67, was a snarling, bloodthirsty gangster who came up through the East Coast underworld as a hit man in the New York mafia’s dreaded Murder, Inc. enforcement wing. He groomed Billy Grasso in the rackets but ultimately fell victim to his protégé’s lofty ambitions. It was later revealed that Tropiano debriefed with the FBI in the 1970s to get a prison term for shaking down trash hauling firms shortened.

5 Thomas (Tommy the Enforcer) DeBrizzi: February 4, 1988 – The brutish, broad-shouldered 65-year old Fairfield County mob chief for the Gambino crime family was found frozen stiff in the trunk of his Cadillac in a Trumbull, Connecticut shopping mall parking lot. He had fallen out of favor with flashy Gambino boss John Gotti when he repeatedly refused to come to New York to report to the Dapper Don face-to-face and had been shot four times in the head, chest and neck.

6 Frank (Frankie Cigars) Piccolo: September 19, 1981 – The Gambino crime family’s Connecticut crew boss was gunned down outside a Bridgeport telephone booth across the street from his makeshift headquarters at the Bagel King on Main Street. The 58-year old industrious capo angered Gambino boss Paul Castellano when he began pushing into Genovese crime family territory in Bridgeport and New Haven, jeopardizing the lucrative and longstanding business relationship between the two syndicates. At the time of his death, he was facing trial on charges of trying to extort Las Vegas entertainer Wayne Newton. Some in the Genovese clan called Piccolo, “The Attorney,” for his argumentative ways.

7 Paolo (Paul the Greaser) Agresta: July 4, 1974 – A Gambino crime family drug and gambling lieutenant in Connecticut, Agresta disappeared on his way to a July 4 barbeque. He was one of Frank Piccolo’s main advisors and acted as one of the Gambino’s representatives for mob business in Canada. The Italian-born Agresta, 68, based his narcotics and gambling activity in the Bridgeport and Stamford areas. He reportedly had been in a beef with Billy Grasso following Grasso’s release from prison in 1973.

8 Richard (Richie the Pistol) Biondi: December 23, 1968 –The feared Connecticut mobster and Midgie Annunziato’s top enforcer is killed inside his apartment in New Haven, a casualty of Annunziato’s war with Irish gang leader Eddie Devlin. Biondi had threatened a group of Devlin’s men that morning over the phone and they responded by going to his apartment and machine gunning him to death when he opened his front door. Annunziato responded by having a Devlin soldier named Charlie Fray executed.

9 John (Johnny Slew) Palmieri: November 10, 1974 – The Gambino crime family’s Connecticut lieutenant was blown up in a car bomb stashed in his trunk on Eastern Street in New Haven. The 59-year old produce wholesaler and explosives expert for the mob was on the losing end of a turf battle with Billy Grasso. Like Grasso, Palmieri had just come home from a stint behind bars and felt entitled to a bigger share of the New Haven racket pie.

10 Thomas (Tommy the Blonde) Vastano: January 28, 1980 – The Genovese crime family soldier was shot to death in the backyard of his Stratford, Connecticut residence. Vastano, 71, had picked up Midgie Annunziato at his home the day he vanished and was considered a top suspect in his homicide. He was also scheduled to testify at an upcoming grand jury probing illegal gambling networks doing business in Bridgeport.

11 Salvatore (Mickey the Face) Caruana: May 1987 – The Patriarca crime family’s “marijuana guy” and one of Billy Grasso’s top earners while living across the state line in Peabody, Massachusetts, disappeared after being last sighted hiding out in a hotel in Groton, Connecticut. Caruana, 49, was dodging a federal drug trial and according to an informant Grasso worried that he would give him up to the feds to get out of his narcotics case, so he killed him in a garage in Hamden. His vehicle was found abandoned at a Connecticut truck stop and wiped of prints.

12 Billy (Hot Dog) Grant: May 18, 1988 – The slick mob gambling chief and popular East Hartford restaurateur disappeared after suspicions grew that he was an FBI informant. Linked to the Patriarca, Genovese and Colombo crime families, Grant, 45, was last seen leaving his South End Seaport establishment. He had previously owned Augie & Ray’s, a heavily-frequented hamburger and hot dog joint. Rumors circulated that he was slain in the parking lot of the West Farms Mall in Farmington for giving up the whereabouts of Colombo mob administrator Alphonse (Alley Boy) Persico , who was apprehended in 1987 on the run from a murder and racketeering case.

13 Thomas (Tommy Pinocchio) Rispoli: November 24, 1962 – The low-level New Haven hoodlum popped up dead two weeks after getting into a physical altercation with Whitey Tropiano and Billy Grasso over a gambling debt. Rispoli’s naked and battered body was discovered in a Branford, Connecticut basement – his skull had been smashed in with a blunt object and he was shot three times. Rispoli, 32, felt Tropiano’s sports book owed him $1,500 for a bet he made on a horse race, however, Tropiano accused Rispoli of “past-posting,” placing his bet once the race was already over, and refused to pay him anything but his original wager back. An incensed Rispoli attacked Tropiano and Grasso and sent Tropiano to the hospital with injuries sustained.

14 Eric Miller: December 27, 1988 – The Hartford boxer, gym owner and reputed drug dealer was found shot in the back of the head behind wheel of his Chevy Blazer on Ledyard Street following a nasty dustup with Patriarca crime family underboss Billy Grasso. The pair had gotten into a heated argument in front of Grasso’s New Haven headquarters, Franco’s, a posh Italian eatery on Franklin Street, two months before when Grasso took offense to Miller’s use of Italian ethnic slurs in a ball-busting session with one of his soldiers. Grasso lunged at Miller with gardening clippers and Miller knocked him out with an uppercut to the chin.

15 Billy Shamansky: April 7, 1980 – The Gambino crime family associate was shot dead in a high-speed chase with his killers on the Merritt Parkway in Stratford. The 41-year old Shamansky was a thief and independent strong arm used for collecting Gambino gambling debts in Connecticut. The suspected triggerman in the brazen hit, Joey Rabbitt, another Gambino enforcer, was found dead four days later with two bullets in the back of his head behind the wheel of his car in the parking lot of a Howard Johnson’s diner in Stamford.

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