Whacked by the Good Guys

Oct 14, 2009 - by Allan May - 0 Comments

Vincent "The Schemer" Drucci

Vincent "The Schemer" Drucci

Vincent "The Schemer" Drucci had the shortest tenure of any of Chicago’s North Side gang leaders. An Italian, he headed a gang that was dominated by Irish, German and Polish criminals. A mob rarity, he was given a 21-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.

by Allan May

Vincent "The Schemer" Drucci had the shortest tenure of any of Chicago’s North Side gang leaders. An Italian, he headed a gang that was dominated by Irish, German and Polish criminals. A mob rarity, he was given a 21-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 his enemies."

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 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 Nov. 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 burial Torrio and his protégé Al Capone stood glaring at Weiss, Drucci and Moran from opposite sides of the grave.

The North Sider’s first attempt at retaliation came on Jan. 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 12 days later, the trio of Weiss, Drucci and Moran struck again. They shot and seriously wounded Johnny Torrio as he arrived 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 reins over to the 25-year-old Capone, served a short prison sentence, and retired from the Chicago rackets.

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 (the third Genna bother to die in just 44 days). Drucci completed this bloody shooting spree on Nov. 13 when he fatally wounded "Samoots" Amatuna in a barbershop.

Over the next 10 months the warfare quieted. Part of this was because Capone was lying low in the wake of the murder of William H. McSwiggin, an assistant state’s attorney for Cook County. The peace would come to an end on Aug. 3, 1926, when two little boys discovered the battered body of Capone’s latest chauffeur, Anthony Curinglone, stuffed into a cistern. He had been beaten and tortured before he had been shot in the head. Curinglone, known as Tommy Ross, had been abducted over a month earlier.

At the time Drucci had been living at the Congress Hotel on South Michigan Avenue. On the morning of Aug. 10, he had breakfast with Weiss. Around 10 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 30 shots were fired. The bullets hit automobiles, smashed shop windows and thudded into buildings. Miraculously the only injury was a leg wound suffered by a bystander.

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 questioning 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 was never fully explained. He stated he was about to close a real-estate deal. Also, unexplained was what Drucci and Weiss’ meeting with Eller was to be about. Waiting in Eller’s office that day 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 Sept. 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 was Louis Barko, who was hit in the right shoulder.

After one failed attempt at a peace settlement, Capone struck back. On Oct. 11, an 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 70 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 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 marred previous election days, had been put on alert to pick up any known troublemakers on sight. The Illinois National Guard was also on standby.

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 Streets. 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 Drucci’s release was prepared. 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 lap.

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. Green rushed to see Chief of Detectives William Schoemaker, demanding 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 the body. Upon seeing Drucci’s corpse 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’Banion’s partner in the flower business.

Drucci was buried the following day after a funeral service 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 12 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, 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 by Allan May

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