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1. St. Valentine's Day Massacre

Date: 1929

Murdered: Peter Gusenberg, Frank Gusenberg, Albert Kachellek, Adam Heyer, Reinhart Schwimmer, Albert Weinshank, John May

Committed for a number of reasons, (including trying to cripple the North Side Gang and in retaliation for Bugs Moran—leader of the North Side Gang—“muscling in” on Al Capone’ dog track in Chicago’s’ suburbs) the St Valentine’s Day Massacre was the worst mob-hit ever seen in the USA. It succeeded in impeding the North Side Gang, but also made life much more difficult for Capone. Bugs Moran escaped the hit because one of the look-outs mistook one of Moran’s men for Moran. Four men carried out the massacre, two dressed in trench coats, two in police uniforms. Some say that Moran fled when he saw the police entering the building, thus sparing his life.

2. "Machine Gun" Jack McGurn

Date: 1936

Murdered: “Machine Gun” Jack McGurn (born Vincenzo Antonio Gibaldi)

McGurn was gunned down, while bowling, by three men with machine guns. The identity and motive are not known. However, two theories are widely accepted: 1) Revenge for McGurns’ supposed involvement in the Valentine’s Day massacre. 2) Silencing heavy drinker and braggart McGurn by the South Side gang. A poem was found in his right hand and a nickel in his left. (McGurn had been known to press nickels into his victim’s hands)

3. Benjamin “Bugsy” Siegel

Date: 1947Murdered: Benjamin “Bugsy” Siegel (born Benjamin Siegelbaum)

Siegel, in an effort to reinvent and legitimize himself, had moved to Las Vegas to oversee the construction of the Flamingo resort. He failed miserably at the job and then was murdered just months after the casino went nearly bankrupt. While reading the Los Angeles Times, Siegel was hot many times through a window by a .30 caliber military M1 Carbine. The crime is unsolved, but his failure in Las Vegas makes me suspicious. A memorial to Bugsy is still located in the Flamingo Hotel neat the wedding chapel.

4. Albert “The Mad Hatter” Anastasia

Date: 1957Murdered: Albert “The Mad Hatter” Anastasia (born Umberto Anastasio)The brutal and violent head of the Mangano/Gambino family mob, was brought down while in his barber’s chair. His bodyguard had conveniently taken a walk when two masked gunmen burst into the shop and opened fire on Anastasia. They continued to shoot until he collapsed to the floor dead, and then shot him point blank in the back of the head. It is believed that Larry and Joe Gallo carried out the murder under a contract from Don Vito Genovese. Anastasia’s wife maintained his innocence of any mob involvement or violence and wanted him to be remembered as a loving and devoted, churchgoing, husband and father.5. Carmine “Cigar/Lilo” Galante

Date: 1979Murdered: Carmine “Cigar/Lilo” Galante, Leonard Coppola, Guiseppe Turano

Galante was having lunch at Joe and Mary’s Restaurant when three men burst in and began to shoot. Cesare Bonventre, one of Galante’s mafia recruits, did nothing to stop the murder and left the restaurant calmly. “Cigar” had created the modern drug trafficking business and began keeping more and more drug money from his bosses. Galente had recently asked the Mafia’ s governing commission if he could retire. His request was granted but then it was learned that he had 30 “greenies” working for him. The Mafia commission is said to have met again and decided it was time for Galante to “permanently retire.” The legacy of drug trafficking and associated crime left Bushwick, Brooklyn in shambles for decades after his murder.

6. Angelo “The Gentle Don” Bruno

Date: 1980Murdered: Angelo “The Gentle Don” Bruno (born Angelo Annaloro)Angelo Bruno was killed by a single gun shot blast in the back of his head while sitting in his car. He had developed many enemies by cashing in on the heroin market in Philadelphia while other families were barred from narcotic distribution. Antonio Caponigro (aka Tony Bananas) ordered the killing but was himself killed just a few weeks later in retaliation. Dollar bills were found stuffed in his mouth and anus—to symbolize greed. The Philadelphia Family went into decline after Bruno’s death.

7. Paul “Big Paul” Castellano

 Date: 1985Murdered: Paul “Big Paul” Castellano (born Constantino Paul Castellano), Tommy BilottiBig Paul” had become jealous of John Gotti’s drug dealing and threatened to kill anyone involved with narcotics. He had also acquired enemies when he did not attend the funeral of Aneillo “Neil” Dellacroce, one of his underbosses, and then named Tommy Bilotti, a body guard, as a new underboss despite Bilotti’s lack of skills for the job. Castellano and Bilottie were shot dead outside a steak house by order of John Gotti. The men had been lured there with the promise of having a talk with Gotti to “iron things out.”