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For two years after the death of North Side gang leader
Dion O’Banion, Vincent “Schemer” Drucci and Earl “Hymie”
Weiss played a dangerous game with Al Capone and his
well-armed gang of South Side gunmen. There was little
chance for Dion O’Banion’s successors to do more than
maintain the territorial boundaries that already
existed, but Drucci and Weiss were motivated by revenge
and wanted to strike back at those who had slain
O’Banion.
Weiss struck hard at the South Side Outfit first,
mortally wounding Johnny Torrio outside of his home.
Torrio survived the attack and after jail time for
earlier liquor charges, he fled Chicago, leaving his
criminal empire to Al Capone. He was now the top man in
Chicago, but he had a bloody gang war on his hands.
Hymie Weiss offered to stem further violence by having
Capone hand John Scalise and Albert Anselmi over to him.
It was a poorly kept secret that they had been in the
flower shop when O'Banion had been murdered. Capone
refused and made plans to knock off Hymie Weiss instead.
He was too slow, though. Weiss and George Moran had
already planned their next move.
On May 26, 1925, they murdered Angelo Genna, one of
Capone’s supporters. A month later, Mike Genna was
killed by the police as he, John Scalise and Albert
Anselmi were about to ambush George Moran. Scalise and
Anselmi killed two police officers before escaping. Tony
Genna was murdered soon after by the Gennas’ own gunman,
Giuseppe Nerone, who may have been paid to assassinate
him by Capone in an effort to stem the bloodshed. The
surviving Gennas soon left for Italy.
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Earl "Hymie" Weiss |

Vincent "The Schemer"
Drucci |
Capone retaliated next. He marked Drucci and Weiss for
death and assigned gunman Louis Barko to carry out the
murders on August 10, 1926. The event became known as
the “Battle of Michigan Avenue”.
Drucci maintained a resident at the Congress Hotel, four
blocks north of the Standard Oil Building at Ninth
Street and Michigan Avenue. On the morning of August 10,
following a late breakfast, Weiss and Drucci met at the
Congress and walked toward the Standard Oil Building,
where they were to meet with Morris Eller, a Sanitary
District Trustee. Eller was the mobbed-up boss of the
Twentieth Ward and a cheap racketeer who offered a
presentable face as a politician. Drucci was carrying
$13,200 in cash in his pockets, which was allegedly a
down payment on a piece of real estate, but was more
likely bribe money for the North Side gang’s Twentieth
Ward sponsors.
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The Congress Hotel on
Michigan Avenue |
As Drucci and Weiss were about to pass through the
neo-Italian Renaissance doors of the building, Louis Barko and
three other men jumped out of a car on the east side of Michigan
Avenue and opened fire on them. Windows shattered and bullets
chipped at stone walls as Drucci scrambled for cover behind
parked cars. Weiss managed to get into the lobby of the
building, shaken but unhurt. Drucci pulled out his own gun and
returned fire before commandeering an automobile that belonged
to C.C. Bassett, a startled motorist who had been trapped in the
crossfire. Drucci’s escape was interrupted by the arrival of the
police, who dragged him off the car’s running board. The affair
turned out to be a bloodless one and it was over in less than
two minutes.
When questioned by the police at the South Clark Street station,
Drucci denied knowing Barko and dismissed the whole thing as an
attempted robbery. Hymie Weiss’ mother, Mary, posted the
necessary bond and freed her son’s friend from behind bars.
Drucci was lucky that day, but his luck didn’t hold out for
long. In April 1927, he was shot to death by Detective Sergeant
Daniel F. Healy on the eve of the city’s mayoral election.
Police radio cars had been issued orders to arrest all gangsters
on sight and while making the rounds on the North Side, Healy
and his squad spotted Drucci, who was carrying a gun. Feeling
harassed, Drucci chided Healy and the other officers and
allegedly threatened them. The altercation turned violent and
Drucci attacked the detective, who had a gun in the gangster’s
rib cage. Healy shot him four times and Drucci was dead before
he hit the sidewalk. Al Capone couldn’t be blamed for this one.
After the shootout at the Standard Oil Building, the opposing
gangs agreed to a peace conference. Capone again denied Weiss’
request to mete out punishment to O’Banion’s killers so Weiss
and George Moran led a hasty assault on Capone’s club, the Four
Deuces at 2222 South Wabash. Capone somehow escaped unhurt but
his driver, Tony Ross, died behind the wheel.
A week later, on September 20, 1926, Weiss pulled another crazy
stunt, this time sealing his fate. He sent a caravan of motor
cars, each carrying a trio of machine gunners, to Capone’s
Cicero headquarters, the Hawthorne Inn. Seated at a table in the
crowded coffee shop, Capone was thrown to the floor by his
bodyguard as the first volley of shots was fired into the
storefront. The hotel was riddled with bullets but Capone
escaped death again. That violent incident was Weiss’ one moment
of glory and revenge for O'Banion's murder. And while he
continued to live a fearless life (to the point of stupidity)
and to goad Capone at every opportunity, his days were numbered.

Holy Name Cathedral |
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On October 11, Weiss was attending the murder
trial of "Polack Joe" Saltis and his driver
Frank "Lefty" Koncil, and decided to take a
break and return to his office above O'Banion's
old flower shop. As Weiss and gunman Patrick
Murray drove toward the office, they had no idea
that four machine gunners were waiting for them.
These men, believed to be John Scalise, Albert
Anselmi, Frank Diamond and Frank Nitti, were
hiding on the third floor of a nearby building.
Weiss was a marked man as soon as he left his
car on Superior Street, just south of Holy Name
Cathedral. He approached the flower shop with
Murray by his side and at the deafening sound of
Tommy guns, the pedestrians on the street
scattered. |

The body of Patrick
Murray on the sidewalk outside of the flower
shop. |
Murray died instantly but Weiss took 10 bullets and
survived long enough to be pronounced dead at
Henrotin Hospital without regaining consciousness.
The bullets that killed Weiss tore away portions of
the inscription on the church's cornerstone and left
bullet holes as a graphic reminder of the event. The
church tried to obliterate them years later but the
chips and marks remain. They can still be seen on
the corner of the cathedral today.
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The second floor windows at 738 North State Street used
by the killers. Cigarette butts and bullet casings were
found on the floor. |
Meanwhile, the assassins fled their third-floor lair,
exited the rear of the building and disappeared into the
crowds along Dearborn Street. A discarded machine gun
was found in an alley off Dearborn but it couldn't be
traced back to the killers.
Although one has to wonder how hard the police looked
for them. Chief Morgan Collins issued a gruff statement:
"I don't want to encourage the business, but if somebody
has to be killed, it's a good thing the gangsters are
murdering themselves off. It saves trouble for the
police."
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Death Photo of "Hymie"
Weiss |
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