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History's Most InFamous Mob Murders of All Time

By Christian Cipollini for MobCity Productions

Rubout, whacked, and taken for a ride are just a few examples of the colorful jargon synonymous with underworld reprisal. All such terms refer to the end result of Ann ultimate edict no wiseguy wants levied against them - the death sentence. Despite the sensational shock and awe that makes mobsters famous (not a good thing for a badguy to be), gangland hits are not the norm, at least not in a perfect underworld, but the reality is this: organized crime is a self-policing entity and as such, sadly, violence is a useful, if not necessary tool for keeping the machinery of vice rackets in motion. Notwithstanding the hyper-violent exceptions, if the mob-as-a-whole had a choice, then violence would always be contained, used only a last resort. Remember kids, outrageous indignation and brazen bloodshed brings unwanted attention to the greater organization!

The twentieth century had no shortage of headline-making mob hits, of virtually every variety, big names and lesser known victims. The crimes covered the spectrum from quietly executed to cruelly excessive, audacious to unconscionable. There were far too many morbidly sensational incidents to cover all in one blog, so here’s five of the most infamous examples of organized crime’s brutality.

5. Carmine Galante, 1979

Carmine Galante

Power can be intoxicating, yet also very deadly. Carmine Galante, would-be boss of the Bonanno crime family and a pioneering force in the evolution of the mob’s stranglehold on narcotics traffic in the French Connection era, is one such example of the bad things that can happen when you get too greedy. Galante had a long criminal history, but was most credited for building the metaphorical heroin pipeline, thanks largely to establishing strong alliances with Canadian mob factions. The Bonanno family more or less had a lock on the smack trade for quite some time. That control however may have not been enough to satisfy the family underboss, as demonstrated when he took over, unofficially, as big boss shortly after recognized boss Philip Rastelli went to prison in 1976. Galante was suspected of ordering numerous murders of rivals from other mafia families, causing deeper rifts between him and the entire mob’s governing body - The Commission.

Additionally, turmoil brewed within his own family, as Rastelli loyalists began seeking the commission’s approval to depose their unsanctioned leader. Ultimately, Galante’s stranglehold and indispensability in narcotics traffic wasn’t what it used to be either. He’d spent so much of the 1960s and 70s in prison while everything in the underworld was undergoing changes and realignments. Galante was by that time, as some have described him, outdated.

On July 12, at 2:45 pm, three men wearing ski masks entered Joe and Mary’s Italian American Restaurant in Brooklyn. They swiftly moved to the back section, outdoors to a patio where Carmine Galante was having lunch, a party of five people. As the trio of masked men who were armed with handguns and shotguns approached the table - Galante’s two bodyguards stepped aside. Then, all hell broke loose and in a matter of seconds three bodies lay lifeless: Galante, Bonanno capo Leonardo Coppola and restaurant owner Giuseppe Turano. The image of the aftermath is perhaps one of the more recognizable visuals of mob brutality - Galante, still with cigar pressed between his lips.

4. Albert Anastasia, 1957

Albert Anastasia

Known by two sinister nicknames - The Mad Hatter and Lord High Executioner - Albert Anastasia’s reputation preceded him. A violent guy he was indeed, but also a longtime loyal ally of the mob’s heyday elites, including Lucky Luciano, Frank Costello and Meyer Lansky. However, much like the cloak and dagger activities of any political or corporate theater, the American underworld

had its share of broken alliances, backstabbing and violent coups. Anastasia managed to escape persecution for his role as a Murder Inc. chieftain and even deposed his own boss (Vincent Mangano) to seize control of the family. Anastasia’s penchant for violent had become a bit too erratic for even his longtime pals following the murder of a witness to a crime Anastasia and the mob as a whole had absolutely no connection.

It was purely vengeance against a perceived squealer, but that’s all Anastasia needed to order the man murdered. That incident coupled with a nefarious conspiracy in the works and planned by Vito Genovese and Carlo Gambino (to put the latter as head of the Anastasia family) basically spelled the end for the Mad Hatter.

Anastasia’s curtain call came while he was receiving a shave in Manhattan’s Park Central Hotel, October 25, 1957. Two gunmen entered, motioned for the barber to step away, and blasted Albert into the netherworld. There were hundreds taken in for questioning over the following years. Among the ‘persons of interest’ – Meyer Lansky, Frank Erickson, George Uffner, and Liz Renay – a star of burlesque and film. While nobody was ever prosecuted for the murder, rumors have long suggested one of the killers was Profaci member Joe Gallo.

3. Benjamin Bugsy Siegel, 1947

Benjamin Bugsy Siegel

In stark contrast to Hollywood versions or fictional tall tales that were once believed, Las Vegas was not founded by a dreamy-eyed gangster, nor was said gangster’s lush casino project an idea he pulled from the dry desert air one day in an ‘epiphany’ moment. However, the future fortune and fame of Las Vegas was indeed the by-product of that one infamous mobster’s effort, and sadly, his violent death. Of course we’re talking about Benjamin Siegel. You may know him better as Bugsy, and his elaborate scheme to create the ultimate high class complex, aka The Flamingo. He didn’t invent the place, but he was the first mob casualty of it.

death of Benjamin Bugsy Siegel

It was nearly midnight on June 20th, 1947, when Benjamin “Bugsy” Siegel sat down on the floral print couch in the living room area of his girlfriend Virginia Hill’s Beverly Hill home. She was in Paris at the time. Allen Smiley, a close friend of Siegel’s, was seated on the other side of the same couch. The pair chatted while Siegel thumbed through the Los Angeles Times. Virginia’s brother Chick Hill and a secretary, Jerri Mason, were in an upstairs room. Outside the house someone laid in wait, peering through the front window, aiming a 30-30 carbine rifle, which conveniently had the firing pin ground. The only thing separating the shadowy assassin from his target was a 14 inch square pane of glass and a distance of four and a half feet. The figure took one last drag of smoke, ground the butt out, and then unleashed the fury of nine rapid fire rounds. The first slammed into Siegel’s head, the second passed through Smiley’s coat. Four rounds in all pierced the intended mark. Within hours of Siegel’s death, top brass from the Jewish faction of mob marched into the Flamingo lobby and announced the place was under new management. Who hit the Bug? Anybody’s guess, but a handful of plausible theories are still being explored and debated to this day, literally with new information and/or revelations (or claims thereof) popping up for discussion rather frequently.

2. Paul Castellano, 1985

Paul Castellano

Big Paul ruled from a posh pad in exclusive Todt Hill on Staten Island. He was, as some would describe, more of a white collar kind of gangster, not a guy who had a full grasp on the real inner-workings of the mob, at least not from the perspective of the people on the streets doing the work. Castellano was bestowed the crown of the Gambino family in1976 by its namesake, the then-ailing Carlo Gambino, who died shortly thereafter. That moment set the stage for trouble that would take almost a full decade to materialize. Right from the getgo some members of the crime family felt dismayed and downright pissed when the obvious choice - Gambino’s underboss Aniello Dellacroce - got surpassed; i.e. Neil got shafted because Paul was related (as both a cousin and in-law) to Carlo. According to legend, Neil Dellacroce was a likable leader; Paul Castellano was out of touch. Dellacroce, an old school mobster with diplomacy skills, took the decision as a stand up guy and kept the peace. One of Neil’s crew members however would never forget the perceived affront -an up and comer named John Gotti, a brash street guy who looked up to Neil with high regard.

As the 70s faded and the new decade dawned, the Gambino family rode high. Law enforcement considered them the most powerful of the five families at the time. That recognition put more heat not only the Gambinos but the entire New York mob. As such, a series of legal blows ensued, of which Paul Castellano was front and center. But there was other family drama running currently as well. In 1984 Paul Castellano learned wire tap tapes of Gambino soldier Angelo Ruggerio were going to be used by the government in his (Castellano) trial. Gotti’s crew had the transcripts and much of what Ruggerio was caught on tape discussing was also a big no-no edict issued by the family boss - no drug dealing. (Side note: it’s a myth that the mob hierarchy embraced a ‘say no to drugs’ policy. To be clear, dope was gigantic business for the mafia dating back to the 1920s. Castellano was one of the few exceptions and his ideology behind it is alleged to have solely been about minimizing the legal problems that narcotics certainly carried.) Big Paul went to underboss Dellacroce and demanded the transcripts be handed over. Dellacroce stalled, as did his underlings including Gotti, because Castellano made it abundantly clear that the penalty for dope slinging was death. Twists and turns to this Cosa Nostra melodrama continued into 1985. And then… all hell broke loose.

Aniello Dellacroce died of cancer on December 2. Adding fury to Gotti’s grief, the family Don didn’t show up for the funeral. His reasoning - essentially it would not be helpful to his own criminal case if he attended another mobster’s funeral. Filling the void left by Dellacroce’s death, Castellano placed Thomas Bilotti in the underboss position, a spot he wouldn’t have much time to relish in.

On the evening of December 16, 1985, as they pulled to the curb of Sparks Steakhouse in Manhattan, Paul Castellano and Thomas Bilotti were riddled with bullets fired from the guns of multiple assailants. Nearby, watching closely from a parked car, John Gotti and Sammy ‘The Bull’ Gravano. The hit was and remains the most audacious and public in recent mob history; a coup d’etat of historical proportions. Within three days of the brazen executions a purported and potential successor’s name made the papers. That of course was John Gotti and he would also become the contemporary face and household name for all things mafia in America.

  1. St. Valentine’s Day Massacre, 1929

St. Valentine’s Day Massacre

Placing their hands against the back interior wall of the SMC Cartage garage in Chicago’s North Side, seven men followed the orders of who they thought were gun-wielding uniformed and plainclothes police. Seconds later… they all felt the sting of .45 caliber rounds and 12 gauge shell fragments piercing their bodies. A sickening sight of pure carnage forever scarred the holiday of love.

The only survivor of the St. Valentine’s Day Massacre – a visibly shaken German shepherd named Highball that belonged to the garage mechanic, John May. Far from a whodunnit, investigators quickly surmised who the culprit pulling the strings most likely was. The gruesome messes of dead and near-dead (one died in the hospital) victims were all members of, or associated with the Bug’s Moran North Side Gang – arch rivals of Al Capone’s empire. Al’s was a household name in Chicago, but gained national infamy after that particularly nasty event on Valentine’s Day of 1929. Although forever credited with ordering the massacre, Capone never faced any charges in that case. As for the actual perpetrators? Theories ran the gamut from known Capone minions to possible subcontracting of Detroit’s Purple Gang and hitmen from St. Louis. Again, nobody was ever convicted of the murders.

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