Americans have always had a love-hate relationships
with outlaws, from the folk heroes of the
Old West to the Mafiosi of the 20th century
Jesse James was the subject of dime novels
depicting him as a heroic figure long before
he was killed by Bob Ford.
Wyatt Earp was well acquainted with both sides
of the law.
The roving criminal gangs of the depression
years became national figures, with some openly
rooting for them to elude the lawmen who pursued
them throughout the Midwest.
Bonnie and Clyde were romanticized despite
the spree of murders they carried out, some
simply brutal executions of lawmen.
Following the 1930s organized crime became
less actions by small roving bands, and more
of a business ruled by bosses notorious for
Individual thugs such as Dillinger, Baby Face
Nelson, and the aforementioned Bonnie and
Clyde were replaced by criminals who were
less likely to be killers themselves, but
more than willing to order murder done.
Robbing banks was replaced with robbing citizens
through loan-sharking, confidence games, gambling,
drugs, prostitution, and the corruption of
businesses and labor unions.
Gangster wars in which criminals killed each
other replaced the gunfights between policemen
and criminals, and lawyers became the nemesis
for the gangsters.
Here are 10 of the most notorious gangsters
in American history.
Arnold Rothstein was the first to run organized
crime as a business
His fellow gangsters were so impressed with
the mental acuity of Arnold Rothstein that
he was nicknamed “the Brain.”
Rothstein emerged from the Jewish mob in New
York before Prohibition, and was widely suspected
of fixing sports events in order to profit
from gambling on them.
Boxing matches, baseball, horse racing, dog
racing, and other events were manipulated
by Rothstein through a network of criminals
whom he employed full-time, as well as enforcers
to whom he turned when it was perceived that
disciplinary measures were called for.
It was Rothstein who most likely arranged
the fixed World Series involving the Black
Sox in 1919, though neither the fix nor his
involvement has ever been proved.
Rothstein was one of the first to exploit
Prohibition through bootlegging, and the organization
he built for the purpose included many of
the more famous underworld names of the period.
Legs Diamond, Dutch Schultz, Meyer Lansky
and Charles Luciano, later known as Lucky,
were all part of his criminal enterprises.
He became the arbiter of disputes between
various gangs, and his decisions were respected
Rothstein was killed when he refused to pay
a debt he incurred from a poker game which
he alleged was rigged.
He refused to identify the gunman as he lay
dying, telling the police that they should
stick to their business and he would stick
The breakup of his criminal empire led to
many of the gang wars of the 1930s.
Al Capone used the widespread corruption of
Chicago’s government to build his empire
The original Scarface rose, if that is the
word, from the tough New York City gangs of
Five Points to become a bouncer in mob controlled
brothels in that city before moving to Chicago
as a personal bodyguard to gangster and bootlegger
A gang war between the city’s North and
South side gangs led to Torrio being almost
Wisely choosing retirement, Torrio handed
his control of the South side to Capone, who
ruthlessly expanded his operations, becoming
the leading supplier of illegal booze in Chicago,
as well as seizing control of illegal rackets,
brothels, and a large segment of the city
At the same time Capone harbored the goodwill
of many citizens, through soup kitchens, offers
of employment, and other activities which
brought him the reputation of a new Robin
Capone flaunted his wealth with expensive
suits, jewelry, cars, women, and food.
He purchased entire trains of sleeping cars
to carry himself and his entourage to Florida
vacations, though his increasing paranoia
led him to doubt all but his closest associates.
How many murders can be lain at his feet is
debated, though his guilt in ordering and
planning the famed St. Valentine’s Day Massacre
is well established.
Whether he once beat three former associates
to death with a baseball bat is debated by
scholars, though such an act was certainly
within character for the gangster.
Capone died from syphilis after serving a
term in federal custody for tax evasion, but
the criminal empire he founded – known as
The Outfit – continues to operate in Chicago
to this day.
Charles Luciano created the modern criminal
organization known colloquially as the Mob
Charles “Lucky” Luciano was another tough
street punk who was mentored by Arnold Rothstein,
along with his fellow gangsters Vito Genovese,
Joe Masseria, Frank Costello, and others in
the criminal pantheon of the 1930s.
Besides teaching Luciano the rudiments of
operating a crime syndicate featuring bootlegged
liquor, brothels, and the numbers rackets,
Rothstein taught his young charge how to scour
off the marks of the street hood and become
accepted in polite society.
Luciano became as comfortable ordering dinner
at New York’s finest restaurants as he was
buying a hot dog at Nathan’s.
By the mid-1920s Luciano was one of Joe Masseria’s
most trusted aides.
Luciano returned that trust by having Masseria
killed, with one of the gunmen a thug by the
name of Benjamin “Bugsy” Siegel.
It was not Luciano who first organized the
Five Families of the Cosa Nostra as is widely
Salvatore Marranzano deserves that bow, and
after placing Luciano at the head of one of
the five families, Luciano had him killed.
Luciano then reorganized the Five Families,
setting up the Commission to resolve disputes
After many years of investigations federal
prosecutors led by Thomas E. Dewey finally
convicted Luciano on charges of pandering
From federal prison he continued to control
organized crime in New York and New Jersey.
In 1942 he entered into a secret agreement
with the US government to ensure the docks
of New York and New Jersey remained in operation,
and he used his Sicilian mob contacts to obtain
information beneficial to the Allies during
the invasions of Sicily and Italy.
He was deported to Sicily after the war, relocated
to Havana, thence back to Italy, where he
continued to control organized crime for many
years, until his death in Naples in 1962.
Dutch Schultz was one of Luciano’s greatest
competitors in New York
Born Arthur Simon Flegenheimer, the gangster
took the more manageable name of Dutch Schultz
while rising to power in New York’s Jewish
gangs of the 1920s.
Schultz’s criminal career began when he
started robbing craps games on the streets
of New York.
The name Schultz came from his brief period
as a driver for Schultz Trucking Company.
By the mid-1920s, Schultz was working as a
bouncer and enforcer for establishments owned
by associates of the Italian gangs in New
In 1928, Arnold Rothstein was shot and eventually
died from his wounds; it was widely believed
that Schultz, by then a powerful New York
bootlegger, had ordered the hit as retaliation
for a fatal attack on his partner, Joey Noe.
No one was ever convicted for Rothstein’s
Schultz committed several murders himself,
one of which was of Jules Modgilewsky, known
as Julie Martin.
Schultz killed Martin by shooting him in the
mouth, before witnesses to whom he apologized
for killing someone in front of them.
After having his operations crippled by aggressive
prosecutions by Thomas Dewey, Schultz appealed
to the Commission for permission to kill Dewey.
Denied, he ordered a hit on Dewey anyway,
Luciano, desirous of taking over Schultz’s
operations, used the disobedience as an excuse
to have Schultz eliminated.
In October, 1935, Schultz was shot by gunmen
working for Murder Inc.
A legend soon arose that Schultz had secreted
over $7 million in cash and bonds in a safe
buried in the Catskills.
The safe, if there was one, has never been
John Dillinger was the king of the roving
gangs of the 1930s
The Depression Era featured roving gangs of
outlaws who crisscrossed the Midwest robbing
banks and stores, engaging in violent and
spectacular shootouts with local law enforcement.
The gangsters included names which became
legendary: Bonnie and Clyde, Baby Face Nelson,
Pretty Boy Floyd, Machine Gun Kelly, and the
king of them all, John Dillinger.
Dillinger was involved in spectacular jail
breakouts, robberies which were marked by
shootouts with the criminals armed with submachine
guns and automatic rifles, car chases, ambushes,
and frequent disappearances.
He attempted to alter his appearance through
plastic surgery, sent taunting letters to
police and newspapers, and became enamored
by the public after his stated goal of not
stealing from the common man, but from the
banks who robbed the people.
Dillinger and his gang, of which there were
several variations, robbed two dozen banks
over the course of less than one year, during
which they also robbed police stations and
armories in search of weapons, as well as
stores and gas stations.
Stealing a car was a commonplace occurrence
for the gang.
During the year of violence Dillinger was
charged with but one homicide, though members
of the gang committed several others.
It was the pursuit of Dillinger which led
the small US Bureau of Investigation to grow
into the Federal Bureau of Investigation.
Killed by law enforcement after he was betrayed
by a brothel owner hoping to avoid deportation,
Dillinger became a legend in life which grew
after his violent death.
He has been portrayed in film numerous times
since, with Warren Oates, Robert Conrad, Mark
Harmon, and Johnny Depp, among several others,
adding their interpretation of his life to
Frank Costello was called the Prime Minister
of the Underworld
Born in Italy, and growing up in New York’s
East Harlem neighborhood where his father
operated a small store, Costello began his
criminal career at the age of thirteen – or
at least that was his age when he first drew
the attention of the police.
Another of the criminal students of Arnold
Rothstein, Costello joined a gang which included
Bugsy Siegel, Meyer Lansky, and Vito Genovese
and which committed robberies, extortion,
loan sharking, bookmaking, and the sale of
When Prohibition began their contacts and
their strong arm tactics were useful to Rothstein
and the bootlegging networks which emerged
during the so-called Great Experiment.
Costello managed to survive the organized
crime wars of the late 1930s (Castellammarese
War) and emerged as a leading associate, the
consigliere, of Lucky Luciano.
Luciano appointed Genovese as the head of
the family when the former went to prison,
and when the latter fled to Sicily to avoid
prosecution on a murder charge in 1937, Costello
became the boss.
Throughout the 1940s Costello grew the family’s
illegal activities and brought in huge profits,
including from operating fixed horse races
in California through his associate Bugsy
In the 1950s Costello became nationally famous
when he testified before the televised Kefauver
Committee hearings which gave the public a
glimpse into the underworld.
Costello survived several prosecutions, for
tax evasion and contempt of Congress, and
an assassination attempt by Genovese in 1956.
He retired the following year and maintained
a residence in the Waldorf Astoria until his
death in 1973.
Bugsy Siegel and the birth of Las Vegas as
a gambling mecca
Bugsy Siegel is often depicted as a victim
of the mob, angered by his failure to generate
immediate profits from his new casino, paid
for with Mafia money.
Siegel was in fact one of the New York mob’s
most violent and ruthless hitmen, who helped
found the notorious killing machine Murder
A boyhood friend of Al Capone, Siegel became
well known for his abilities with knives,
guns, and the garrote, and his willingness
to use them for both pay and his personal
His prowess as a hitman put his own life in
danger, and in 1933 Siegel made the first
of what became several trips to California,
eventually settling there in the late 1930s
with the intent of extending East Coast criminal
enterprises to the West Coast.
Siegel used strong arm backing from New York
to take over Los Angeles’s numbers and bookmaking
Siegel hobnobbed with Hollywood royalty in
California, becoming somewhat of a celebrity
himself as he appeared in public with the
likes of Gary Cooper, Clark Gable, Cary Grant,
and a variety of starlets.
In the 1940s he began construction of the
Flamingo in Las Vegas, using mob money and
promising huge profits when the casino opened.
They failed to appear as promised.
At the same time Siegel skimmed profits from
the other mob operations on the West Coast
he was responsible for, diverting the money
into the Flamingo and into his own pockets.
By late winter 1947, the Flamingo, after opening,
closing, and reopening to great publicity,
was delivering a small profit, but the mob
bosses were tired of waiting.
Siegel was killed by long range rifle shots
while in the home of his girlfriend, Virginia
Hill, on June 20, 1947.
The triggerman who killed the former hitman
was never identified.
Johnny Roselli was recruited by the CIA in
the early 1960s
Johnny Roselli’s criminal career began in
the Chicago of Al Capone while Capone was
still working as a bodyguard for Terrio.
Born Fillippo Sacco, Roselli insinuated himself
into the film industry in California, and
was later heavily involved in extortion activities
against Hollywood producers.
By the 1940s he was well known as an enforcer
for the Chicago Outfit.
It was Roselli who, under orders from The
Outfit, ordered Columbia Pictures’ Harry
Cohn to offer a contract to a young and unknown
actress who had caught the eye of Outfit boss
Cohn, under pressure from Roselli, complied.
The name of the young actress was Marilyn
In the 1960s Roselli was involved with CIA
attempts to kill Fidel Castro in Cuba.
He was a known associate of Frank Sinatra,
who sponsored Roselli’s membership in the
Friars Club, where Roselli was soon involved
in cheating at cards in a widespread scam.
In the 1970s Roselli was linked to an alleged
conspiracy in the murder of John F. Kennedy,
as well as to the disappearance of Jimmy Hoffa.
Roselli testified to the House Committee investigating
the Kennedy assassination in 1975, days before
Sam Giancana was scheduled to testify.
Giancana was shot and killed before he could
In 1976 Roselli was called before the committee
to testify a second time, but Roselli could
not be found.
In August 1976 his dismembered body was discovered
in a steel barrel floating near Miami in Dumfounding
Who killed him has yet to be determined.
Whitey Bulger enjoyed the protection of the
FBI as he committed multiple murders
Few thugs in American history were as remorseless
and ruthless as James Joseph Bulger Jr. Bulger
hated the nickname Whitey, preferring to be
He was eventually indicted for 19 murders
based on the eyewitness testimony of associates,
though he probably killed several more.
He supported IRA terrorists with both money
and weapons, operated loan sharking, bookmaking,
narcotics rings, and other criminal activities,
all while serving as an informant for the
He gave the FBI information regarding the
operations of the Italian Mafia in South Boston,
in exchange for which the FBI looked the other
way regarding Bulger’s activities.
Eventually FBI agent John Connolly tipped
Bulger about his pending arrest, giving the
murderer and extortionist time to flee.
Bulger evaded justice for more than a decade,
during which time he was second only to Osama
Bin Laden on the list of Ten Most Wanted Fugitives.
Throughout his criminal career Bulger had
stashed funds and false identity documents
which helped him in his flight.
Captured in 2013, he was convicted of more
than thirty felonies, including being involved
in 11 murders.
He was sentenced to two life terms plus ten
years, and transferred from one federal prison
to another before being sent to Hazelton,
a high-security federal prison in the mountains
of West Virginia, known to its residents as
Within a few hours of his arrival Whitey Bulger
was beaten to death by inmates who used a
heavy padlock secured in a sock as their weapon.
His eyes were nearly gouged out and his tongue
cut through, organized crime signs of the
victim having been an informant.
Leroy Nicky Barnes created an African American
mob in Harlem
Nicky Barnes was a small time drug dealer
and heroin addict in Harlem when he was sent
to prison in 1965.
While incarcerated he beat his own addiction
and met Joey Gallo, a member of the Colombo
Whether Barnes learned the advantages of organizing
his criminal activities along corporate lines
from Gallo or not is uncertain, but when Barnes
was released he returned to Harlem with a
business model in his head.
In 1972 Barnes formed a seven man organization
he named The Council, along the model of the
Mafia, to more efficiently run narcotics distribution
in New York.
Eventually his operations moved into Pennsylvania
and across the border into Canada, as with
the Mafia including legitimate businesses
to launder money and to mask illegal activities.
Barnes was arrested numerous times, evading
convictions through bribery and extortion,
and earning the sobriquet Mr. Untouchable.
Eventually he was convicted through the federal
courts and imprisoned for life without the
possibility of parole.
Imprisoned, he arranged a deal with prosecutors
through which he provided evidence against
other members of The Council, as well as other
Barnes’s information led to the conviction
of 16 drug traffickers, the indictment of
another 28, and implicated himself in eight
drug related murders.
Barnes was released from federal custody in
1998 and entered the Federal Witness Protection
He has been featured in films including American
Gangster in 2007, in which he was portrayed
by Cuba Gooding Jr.