Allan May, Crime Historian
Allan May is an organized crime historian, writer and lecturer. He also writes a monthly column for the Cleveland Plain Dealer.
Whacked By the Good Guys
By Allan May
Vincent "The Schemer" Drucci left behind quite a legacy. He had the shortest
tenure as the leader of Chicago's North Side gang. An Italian, he headed a gang that was
dominated by Irish, German and Polish criminals. A mob rarity, he was given a twenty-
one gun salute at his funeral. But most notably, he may have been the only mob boss ever
to be killed by a law enforcement officer.
The leaders of the North Side Gang during the 1920s were Dion O'Bannion, Earl
"Hymie" Weiss, Drucci, and George "Bugs" Moran. Of the four, Drucci was said to be
the least known and least influential. The "Schemer" got his nickname from his ability to
come up with hare-brained, "hits, heists and kidnappings." Early in his criminal career he
gained a reputation for breaking into public pay phones. Laurence Bergreen, in his book,
"Capone: The Man and the Era," describes Drucci: "He had a streak of recklessness and
daring, and he looked the part of a gangster - tough, dark, and menacing, his expression
frozen in a tragic mask topped by wild unkempt hair (and) a face to haunt the dreams of
There is very little known about Drucci's early life. One writer states his real
name was DiAmbrosio. He served two years in the navy during World War I receiving an
honorable discharge. After the war he joined with other North Side gang members.
Drucci's short, but violent, career in the mid-1920s seemed more befitting of a Wild West
gunfighter than a big city gangster.
Dion, or Dean, O'Bannion was the first leader of the North Side gang. A colorful
and charismatic boss, he was a former choirboy and in his spare time was a florist. It was
in his florist shop that he was murdered on November 10, 1924 by three gunmen who
came in under the guise of picking up a floral arrangement. O'Bannion had been killed
because of a doublecross he perpetrated against Johnny Torrio. At the funeral Torrio and
his prot‚g‚ Al Capone stood glaring at Weiss, Drucci and Moran from opposite sides of
The North Sider's first attempt at retaliation came on January 12, 1925. Capone's
car was raked by gunfire outside a State Street restaurant, and his bodyguard, Sylvester
Barton, was wounded in the back. This attack caused Capone to order his famous
$30,000 bulletproof Cadillac.
Just twelve days later, the trio of Weiss, Drucci and Moran struck again. They
shot and seriously wounded Johnny Torrio as he was arriving home from an afternoon of
shopping with his wife. Weiss and Moran did the shooting while Drucci stayed behind
the wheel. Moran was about to deliver the coup-de-grace when his gun jammed. Torrio
recovered from his wounds, but decided he had had enough. He turned the reigns over to
the 25 year-old Capone, served a short prison sentence, and retired from the Chicago
Between May and November 1925, Drucci was a suspect in three murders and
was himself wounded. On May 25, Weiss, Drucci and Moran were believed to be the
gunmen who shotgunned Angelo Genna to death. Less than three weeks later, while
Drucci and Moran were laying in wait for Genna gunmen, Scalise and Anselmi, the pair
surprised them instead and riddled Moran's car with bullets slightly wounding Drucci.
On July 8, Drucci was thought to be one of two killers who pumped five slugs
into the back of Tony Genna, who became the third Genna bother to die in just 44 days.
Drucci completed this bloody shooting spree on November 13 when he fatally wounded
"Samoots" Amatuna in a barbershop.
Over the next ten months the warfare quieted. Part of this was due to the fact
Capone was lying low in the wake of the murder of William H. McSwiggin, an Assistant
State's Attorney for Cook County. By August 1926, the battle was heating up again. On
August 3, two young brothers discovered the body of Anthony Curinglone, Capone's
chauffeur, who had replaced the wounded Sylvester Barton. Curinglone, known as
Tommy Ross, had been abducted over a month earlier. He was beaten and tortured before
he was shot in the head and his body stuffed into a cistern.
At the time Drucci had been living at the Congress Hotel on South Michigan
Avenue. On the morning of August 10, he had breakfast with Weiss. Around 10:00 a.m.
the two walked down the street to the Standard Oil Building for a scheduled meeting with
Morris Eller, a sanitary district trustee and the political boss of the 20th Ward. As Drucci
and Weiss began to cross at Michigan and Ninth Streets, an automobile containing three
men pulled up and began blasting away at the two. Pedestrians and Weiss hit the
pavement, while motorists ducked beneath dashboards. Drucci jumped behind a mailbox,
pulled an automatic and returned fire.
Two of the gunmen jumped out of the car to get a better shot at their adversaries.
In all thirty shots were fired. The bullets hit automobiles, smashed shop windows and
thudded into buildings. Miraculously the only injury was a leg wound suffered by an
As police sirens sounded, Weiss was able to slip away. His presence was not even
reported in the newspapers until two days later. The driver of the would-be assassins' car
sped off leaving the two gunmen to make their own escape. Drucci jumped on the
running board of an automobile, pointed his gun at the driver and said, "Take me away,
and make it snappy," an interesting choice of words from the vicious gangster. Police
quickly surrounded the car and arrested Drucci.
At the station, Drucci, who was carrying $13,200, told the police his name was
Frank Walsh. Police had also arrested one of the gunmen, who had dropped his weapon
and was trying to flee. Identified as Louis Barko, a Capone triggerman, he gave his name
as Paul Valerie. Detectives quickly realized who the two men were. Barko was brought
before Drucci who stated, "Never saw him before. It wasn't no gang fight. It was a
stickup, that's all. They were after my roll."
Barko explained that he was just a spectator at the scene and ran because he
"didn't want to be hit by a stray bullet." Although a writ of habeas corpus was applied for
to release Drucci, a judge decided to hold him for inquiry by detectives. Later that night
Drucci was released after bonds of $5,000 - $1,000 for carrying a concealed weapon and
$4,000 for assault with intent to kill - were signed by Mary Weiss, Hymie's mother..
The money Drucci had been carrying that day was never fully explained. He
stated he was about to close a real estate deal. Also, unexplained was what their meeting
with Eller was to be about. Waiting in Eller's office was John Sbarbaro, an Assistant
State's Attorney who was famous for being the underworld's undertaker. His funeral
home had handled the funeral of O'Bannion.
Ironically, five days after the shooting, Drucci and Weiss were driving past the
Standard Oil Building when a car rammed them to the curb and gunmen again began
shooting at them. The two North Siders jumped from the car and ran into the building for
protection firing over their shoulders as they fled.
The retaliation the North Siders planned was a spectacular one. On the afternoon
of September 20, Weiss called out all the troops for an all-out assault on Capone at the
Hawthorne Inn restaurant.* The assault failed and the only gangster wounded,
unbelievably, was Louis Barko, who was hit in the right shoulder.
After one failed attempt at a peace settlement, Capone struck back. On October
11, a Capone planned ambush put an end to Hymie Weiss in front of the Holy Name
Cathedral.* During the ambush, another man was killed and three were wounded.
This vicious double murder incensed the citizens of Chicago, many of whom were
still irate over the murder of McSwiggin less than six months earlier. Capone needed to
do something to suppress the public's indignation. His answer was the Hotel Sherman
Treaty,* a five point peace plan that ended standing grievances and abolished
encroachment on established territories.
In the wake of the Hotel Sherman Treaty, Chicago would see the longest stretch
of peace since Prohibition began. A period of seventy days passed without a single beer-
war murder. Capone invited members of the media over for a sit down dinner he helped
prepare and announced he was retiring. Few believed him.
With peace pervading throughout the city, the news focus was on the upcoming
mayoral election pitting incumbent mayor William E. Dever against former mayor
William Hale "Big Bill" Thompson. On Election Day, Capone thugs were scarce. The
Chicago police, in trying to prevent the violence that marked previous election days, had
been put on alert to pick up any known trouble makers on sight. The Illinois National
Guard was also on stand-by.
Drucci and a couple of henchmen decided they would help the Thompson cause
by kidnapping Alderman Dorsey Crowe, a Dever supporter, on election-day eve. The
night before, they had knocked out a watchman and ransacked Crowe's office. A police
squad on Monday afternoon spotted Drucci and companions Henry Finkelstein and
Albert Single at Diversy and Clark Street. The police halted the trio and a quick search
revealed Drucci was carrying a .45 automatic. The three men were taken to the detective
bureau. Drucci's lawyer, Maurice Green, was called immediately and a writ for his
release was made. Four policemen, including Patrolman Dan Healy and a lieutenant were
assigned to take the trio to the Criminal Courts Building where Green was waiting.
An argument began between Healy and Drucci. The "Schemer" objected to Healy
grabbing his arm and called him a foul name. More words were exchanged. Healy struck
Drucci, pulled his service revolver and said, "Call me that again and I'll let you have it."
The two men continued to argue as all seven piled into a police car.
According to Healy's statement to his superiors, Drucci continued to threaten him
saying, "I'll get you, I'll wait on your doorstep for you." When told to shut up, Drucci
responded, "Go on you kid copper, I'll fix you for this. Take your gun off and I'll kick
hell out of you." With that Drucci slugged Healy in the face and shouted, "I'll take you
and your tool (gun)." As Drucci grabbed the police officer, Healy pulled his revolver and
fired four times hitting Drucci with three shots.
Henry Finkelstein's statement of events differed from Healy's version. Finkelstein
claimed Healy struck Drucci first. A scuffle began in the car and the driver pulled to a
stop on Clark Street. One police officer exited the car followed by Healy who abruptly
stopped, turned on the running board and shot Drucci as he sat there with his hands on his
Single claimed Drucci told Healy to, "Take off your gun and we'll get out and
fight it out." Both men exchanged blows according to Single.
Drucci was taken to Iroquois Hospital. He had bullet wounds in his left arm, right
leg, and one in the abdomen. At Iroquois a dressing was administered and he was rushed
to the county hospital to be treated. Drucci died before they could get him there.
Drucci's attorney, still waiting at the Criminal Courts Building, was informed of
his client's demise. Rushing to the Chief of Detectives, William Schoemaker, Green
demanded that Healy be arrested for murder. The chief replied to Green that, "a medal
was being got ready for Healy." That evening, Drucci's wife, Cecilia, was called to the
morgue to identify his body. Upon seeing him she cried out, "My great big baby."
On Thursday, April 7, Drucci's $10,000, flag draped, aluminum and silver casket
lay in the Sbarbaro & Company funeral home on North Wells Street. It was surrounded
by $30,000 worth of flowers, many of the arrangements arriving from William J.
Schofield, O'Bannion's partner in the flower business.
Drucci was buried the following day after a funeral service was held at
Sbarbaro's. No priest officiated, but family members and several close friends recited
prayers led by the undertaker. The crowd was estimated at 1,000. The hearse, draped in
an American flag, was preceded to the cemetery by twelve carloads of flowers. Drucci's
body was interred at Mount Carmel Cemetery, which would one day be the final resting-
place for Capone.
At the cemetery, mourners bowed their heads as a rifle squad fired a 21-gun salute
and a bugler played taps. Drucci's pretty blond widow, Cecilia, about to inherit a
$400,000 estate, turned to a reporter as she left and said, "A policeman murdered him.
But we sure gave him a grand funeral."
* = Will be covered in future columns.
Copyright © A. R. May 1999