From the infamous St. Valentine's Day Massacre during Prohibition to the brazen killing of
Paul Castellano in midtown Manhattan, the mafia and murder are too often connected.
In the 1920s, the primary rival to Al Capone and Johnny Torrio's
Chicago Outfit was the North Side Gang led by Dean O'Banion and Bugs Moran.
After working as an enforcer for various newspapers, including the Chicago Tribune,
O'Banion and the North Side Gang got into bootlegging when Prohibition hit in the '20s.
"Everybody drank. The general public viewed it as just a silly law."
An uneasy truce prevailed between the O'Banion and Capone gangs for a short time,
but it broke down when Torrio and Capone's associates started to make trouble on the
North Side. On a November night in 1924, three killers hired by Torrio
stepped into O'Banion's florist shop on North State Street. O'Banion was
wearing a specially tailored suit with three hidden gun pockets, but they were useless.
One of the hitmen grabbed O'Banion's hand to shake it,
then he and his associates raked the florist with bullets. When they were done, the killers
fled into a waiting car while associates blocked traffic with their own vehicles.
The North Side Gang would be finished a few years later following the St.
Valentine's Day massacre, leaving Capone in control of Chicago.
When Chicago residents awoke on February 15, 1929, the headlines read like a bombshell:
"7 Chicago Gangsters Slain by Firing Squad of Rivals, Some in Police Uniforms."
"Prohibition had been meant to herald an era of sobriety and
clean living. Instead it was the dawn of unprecedented violence in American life."
Police had discovered the bodies of seven mobsters belonging to Bugs Moran
and Dean O'Banion's North Side Gang inside an illegal alcohol warehouse owned by Moran.
There was a mob war going on between Moran and Al Capone, with both sides competing
for the largest slice of Chicago's bootlegging trade. That morning, Capone decided to end it.
Though the details are murky, it appears as though several executioners hired by Capone confronted
the North Side gangsters at the warehouse under the guise of being police officers.
"This is a raid. Everybody. Against the wall. You know the drill."
They lined them up against the wall, but, instead of arresting them, they mowed them
down with tommy guns. Moran barely escaped death by being late. Jack McGurn was initially indicted
for the murders, but the case was dropped and, nearly a century later, has never been solved.
Born in 1868 in Castellammare del Golfo, Sicily,
Salvatore Maranzano was a prominent gangster during the Prohibition years.
Maranzano came to America after World War I,
landing in New York City. When Prohibition kicked off in the early 1920s, Maranzano
quickly established himself and his crew of fellow Castellammare mobsters as major
players in the bootlegging game. In the fight for control of New York City's liquor trade,
Maranzano found himself in a war against rival mobster Joe "The Boss" Masseria.
After a bloody year that resulted in at least 60 mobster deaths, the feud finally
ended when gangsters led by Charles "Lucky" Luciano gunned down Masseria in a restaurant.
"Crime scene photos show Masseria with an ace
of spades in his hand. A sign of bad luck in some circles."
Afterward, Maranzano tried to declare himself the capo di tutti capi,
or "boss of all bosses." But Luciano had other plans.
On September 10, 1931, acting on Luciano's orders, four gunmen shot Maranzano to death inside his
Park Avenue office while eight terrified witnesses stood outside and listened. Though Al Capone
was initially linked to the murder, most people consider Luciano to have been the mastermind. But,
nearly a century later, no one has yet been officially charged with the killing.
Originally born Arthur Flegenheimer, the infamous mobster Dutch Schultz was
a prominent Prohibition era bootlegger. Schultz smuggled liquor from Canada into New York City,
at one point making as much as $20 million a year.
After Prohibition ended, Schultz was tried for tax evasion,
but he ultimately was acquitted. In 1935, facing federal tax charges once again,
Schultz concocted a plan to have the prosecutor, Thomas E. Dewey, murdered.
"Schultz just completely loses his temper [...] and says,
'I don't care what the Commission has to say. [...] I'm going to do this myself."
The mob was worried about the potential heat the hit would bring down on them. So on October 23,
1935, members of the Jewish crime syndicate Murder, Inc. tracked Schultz to the Palace Chop
House in Newark, New Jersey and shot him multiple times. Schultz fell into a coma and died the next
day without identifying his killer, though it's thought to have been Charlie "Bug" Workman.
"Machine Gun Jack" McGurn was an Italian-born mobster who roamed the Chicago streets during
the years of Prohibition. He allied himself with Al Capone and Johnny Torrio of the Chicago Outfit,
and worked as a personal bodyguard. Having already been implicated in numerous murders,
including that of Illinois state's attorney William McSwiggin and gangster Hymie Weiss
in 1929, McGurn was reportedly involved in organizing the St.
Valentine's Day massacre that took out Capone's rivals in the North Side Gang.
McGurn's alibi for the massacre had been that he was staying with Louise Rolfe,
a woman he later married. When the government couldn't charge him for
the slayings they went to plan b, and, in 1931, McGurn was sentenced to two
years in prison for violating the Mann Act, which prohibits sex trafficking.
On February 15, 1936, the seventh anniversary of the St. Valentine's Day massacre,
McGurn himself was gunned down in a Chicago bowling alley. He was most likely killed
on the orders of Outfit boss and former associate Frank Nitti, though once again,
whoever committed the crime skirted conviction.
One of the most interesting periods of the mafia timeline in America was its takeover
of the Las Vegas casino scene. And one of the first people involved was Jewish
gangster Bugsy Siegel. Siegel grew up in New York and spent the Prohibition years
in the employ of both Meyer Lansky and Charles "Lucky" Luciano. He may have been involved in
the murders of Joe Masseria and Salvatore Maranzano, but that's only speculation.
Still, the mob had him relocate to California to escape police heat.
Siegel went west in 1936 to start racketeering.
"Bugsy's takeover is soon generating enormous profit for Luciano and the mob, totalling,
by 1942, some eight million dollars a year."
By 1945, he was in Las Vegas struggling to build his casino, The Flamingo,
which was being financed by mob money. The casino eventually opened in December 1946,
shut down almost immediately, then reopened in March 1947.
"The cost overruns for the Flamingo were due mostly to excessive skimming by Bugsy Siegel."
Just three months later, on June 21, Siegel was murdered in the Beverly
Hills house of his girlfriend, actress Virginia Hill. The assassin crept up to
a window and fired at Siegel, who was sitting inside. The killer has never been identified.
An Italian-born immigrant to the United States,
Albert Anastasia was a notorious mobster and a member of the brutal Murder,
Inc. crime syndicate that operated under a murder-for-hire business model.
Anastasia has been implicated in numerous killings, including three
he was charged with between 1928 and 1933. He was never convicted
due to the sudden and untimely deaths of all the key witnesses.
Anastasia was rumored to be one of the four gangsters who killed former
capo di tutti capi Salvatore Maranzano in 1931 under the orders of "Lucky" Luciano.
"Within the mafia, Anastasia was recognized as a ruthless, unflinching killer."
Anastasia served in the army for two years during the Second World War,
after which he returned to a life of organized crime. In 1951,
he became the head of what would later become the Gambino Crime Family.
But, on October 25, 1957, Anastasia was getting a shave when two gunmen,
their faces obscured by scarves, shot him to death. The murder was carried
out in full view of 11 other patrons of the barbershop and was done on
the orders of Carlo Gambino, who would soon take control of the family.
Sam Giancana was one of the most infamous mobsters of the 1960s. His crimes were legendary,
and he's been linked to conspiracy theories related to former president
John F. Kennedy's election and his November 1963 assassination.
"The fact that the president and the boss of
the Outfit were sharing women is an incredible story in and of itself."
In 1957, Giancana became head of the Chicago
Outfit after Tony "Joe Batters" Accardo named him his successor.
However, in the 1960s, Giancana lost control of the outfit. Shortly after, he moved to Mexico.
Yet, in 1974 Giancana returned stateside, partly to testify for the CIA involving assassination
plots of Fidel Castro. After being home for just a year, on June 19, 1975, Giancana took
seven shots to the head in his Oak Park home. The FBI noted it had the hallmarks of a mob killing.
"I think that Tony Accardo would have been involved in the decision to have Sam Giancana
killed. [...] Somebody of Sam's stature would have to be approved from the top."
No one had been charged with the murder as of 2023,
but most people think it was Tony Spilotro, an up-and-coming Chicago gangster of the time.
Raised on the streets of East Harlem in New York City, Carmine "The Cigar" Galante
established himself as a serious gangster through ruthless murders and drug dealing.
"He was head of the Bonanno crime family. Known as "The
Cigar," he was widely feared for his cruelty."
He worked with the founders of both the Genovese and Bonanno crime families, eventually becoming
the disputed head of the Bonanno family following a decade-long stint in prison for drugs.
However, The Commission, the American mafia's informal governing body,
had already decided that Phillip "Rusty" Rastelli
was to be the Bonanno boss. Galante started calling himself the capo di tutti capi,
implying he was in control of The Commission, which turned out to be a major mistake.
"Not only did the Commission not want Galante to become head of the Bonanno crime family,
they certainly did not want him to become the boss of bosses."
In retaliation, Rastelli, the recognized boss of the Bonanno family, ordered two of his capos to
infiltrate Galante's inner circle and murder him. On July 12, 1979, in broad daylight, Galante took
a shotgun blast while eating at the Joe and Mary Italian-American Restaurant in Brooklyn.
"Mysteriously, two of Galante's bodyguards,
Baldassare Amato and Cesar Bonventre, were uninjured and walked away unscratched."
In 1986, Anthony "Bruno" Indelicato was convicted of Galante's murder,
but his accomplices were not charged.
There are brazen mob murders and there are audacious mob murders,
but nothing compares to how Paul Castellano was killed in 1985. Prior to his death,
Castellano was the reputed head of the powerful Gambino Crime family. He was
facing charges for racketeering and conspiracy to commit murder, and law enforcement had held
the family responsible for at least 25 extracurricular killings in recent years.
Then, on December 16, 1985, Castellano and associate Thomas Bilotti were both shot to
death after exiting their limousine to eat at a restaurant in midtown Manhattan. The killers,
who used semi-automatic weapons, immediately fled
in a getaway car. The order had been given by a lower-level member of the Gambino family,
John Gotti, who became the new boss following Castellano's death.
It's believed that Gotti ordered the hit on Castellano because he was dealing heroin against
Castellano's wishes. Fearing Castellano was going to have them killed, Gotti and
his associates hit first, with Gotti watching the whole thing from a vantage point nearby.
Notorious mobster Anthony Spilotro was a longtime member of the Chicago Outfit. In the 1970s,
he was sent to Las Vegas to replace Marshall Caifano as an enforcer at
the Stardust, a mob-run casino. Throughout the '70s, Spilotro made Vegas his personal fiefdom,
protecting Frank "Lefty" Rosenthal and the skim at the Stardust casino,
while committing robberies on the side and selling the stolen goods.
"In a town rightly or wrongly labeled as an organized crime stronghold, it was Spilotro
who personified the public perception of mob influence and underworld style."
In the 1980s, after being blackballed from the casinos, Spilotro ran afoul of
the mob by getting arrested numerous times and having an affair with Rosenthal's wife. Then,
in mid-June 1986, Spilotro and his brother were found beaten to death in a "shallow
grave in an Indiana cornfield," as reported by The New York Times.
In 2007, mobster Nicholas Calabrese testified that 10 men had beaten the brothers to death
in an Illinois basement. Both James "Little Jimmy" Marcello
and Calabrese were convicted. Marcello received a sentence of life in prison,
while Calabrese got 12 years. Spilotro's life was famously dramatized by actor Joe
Pesci as the character Nicky Santoro in Martin Scorsese's 1995 film Casino.