Prohibition Chicago

The Northsiders

1924 -- Prelude

 1925 -- War in Chicago

1926 -- "A Real Goddamn Crazy Place!"

October 11, 1926

October 11, 1926
Part II

St. Valentine's Day
Part I  Introduction
Part II Top 10 Myths
Part III 10 Questions
   (and 10 answers)


Photo Gallery






1. The McSwiggin killing created major Chicago newspaper headlines for weeks, and caused Capone public and legal grief. McSwiggin was likely shot only because he happened to be out drinking with rival gangsters targeted by Capone. McSwiggin had met with Capone several times, and they were on the same side during the April 1926 primary elections. McSwiggin's killing was a rare event during the Chicago Prohibition wars: a member of law enforcement killed by the gangs.
There is evidence that Capone himself wielded a machinegun in the drive-by killing (in which two rival gangsters were also killed). 

2. Capone's takeover of Chicago Heights is thoroughly described by Lawrence Bergreen  in "Capone - The Man and the Era". Bergreen's work is evidence of the power of probing research and good writing. Back  

3. Probably Frankie Rio, Tony "Mops" Volpe, and Frank Nitti, coordinated by Barko. Back

4. The hierarchy of Capone's large organization is not easily understood. Various "units" had specific tasks and responsibilities: for shipment and receipt of liquor products, for distribution to bars and clubs, for prostitution management, for territorial enforcement of business, for labor and union rackets, for gambling, for Capone's personal protection, and for special operations. Special operations involved hit assignments, like the Gennas and the Northsiders. It was apparently harder to move laterally between sections than it was to come out of nowhere to achieve upward mobility. Outfit gang members could move up in the organization if they helped plan or were participants in successful hits, or if they were chosen to become Capone bodyguards. Like any business, success bred opportunity and the chance for more success. Scalise and Anselmi made their bones with the O'Banion hit, and were used by Capone from that point for virtually every critical outfit hit for the next five years.

John Scalise   Albert Anselmi

 Typical of monotypic, performance-based organizations, superstars emerged, and shone brilliantly for a while. Jack McGurn and Frank Nitti are two examples of emerging stars who served Capone and impressed him enough to be given increasing responsibilities and assignments (Nitti and McGurn were among Capone's primary bodyguards in 1925-26 [at $7,800 a year], and their success in that assignment allowed each to rapidly move up in the Capone organization).
Louis Barko seems to have been given several opportunities in 1926, but his lack of success led to career stagnation.

5. Kobler in "Capone--The Life and World of Al Capone" writes about a second attempt on Weiss and Drucci in front of the Standard Oil Building on August 15, 1926 (p185). Allsop in "Bootleggers" (p115) also notes the incident. Other than "Wicked City" (which lists the Kobler book in its bibliography), there is no documentation of this second hit, five days later, also in front of the Standard Oil Building. The Chicago Tribune has no reference to a second hit attempt in its 8/16/26-8/18/26 issues. It seems the authors may have confused later mention of the August 10th hit with a second incident. Back  

6. The incident also permanently upped Rio's stock in Capone's eyes. He became Al Capone's most trusted bodyguard and was chosen for a number of critical jobs over the next several years, including being arrested with Capone in Philadelphia (a set-up that allowed Capone to go underground for a while), and uncovering the plot by Scalise and Anselmi to take Capone down. Back  

Frankie Rio

7. In October of 1925, O'Banion made a trip to Louis Alterie's ranch in Colorado. In Denver, he made a huge purchase of automatic weapons (pistols, shotguns, Thompson submachine guns) and ammunition.
A remarkable number of weapons were used in the assault on Cicero.

8. Once the scene was secured, Capone came out to 22nd Street to survey the damage. Not only did he reassure business owners on the block that he would pay for the damage to their property, he sought out Mrs. Freeman to make sure she received prompt medical attention. Capone reportedly spent $5,000 on hospital and surgery bills to repair Freeman's right eye. Back

9. How that meeting came about is open to conjecture. Schoenberg has Torrio and Capone meeting in Florida (p161) immediately after the Cicero assault to discuss what to do about the Weiss problem. Whether in person or by phone, there is very strong evidence Capone conferred with Torrio before deciding on a peace meeting. Talking in lieu of shooting was always Torrio's first choice. Back  

10. That Lombardo was chosen by Capone as his representative demonstrated Capone's sincerity. Mike Merlo played a somewhat similar role between Torrio and O'Banion. As head of the Unione Sicilione, Lombardo did Capone's bidding, but the importance of the position made him a respected middleman. The position would also eventually make him a prime target for the Northsiders after they allied with Joe Aiello in 1927. Back   

11. The Chicago Tribune stated Weiss' demand was the killing of two of the gunmen who attacked Drucci and him outside the Standard Oil Building. But this seems unlikely. Weiss would have chalked up the Standard Oil hit to the normal business of the business. O'Banion's ruthless murder was something Weiss simply could not forgive and forget. Such was the bond between the two men.

1926 -- "A Real Goddamn Crazy Place!"

For Al Capone and Hymie Weiss, the first six months of 1926 would be about the nuts and bolts business of their organizations. Capone busied himself with the logistics of receiving Frankie Yale's shipments of whiskey by truck from New York City. Weiss concerned himself with solidifying his Northside base, negotiating with potential allies, attempting to disrupt Capone's new liquor deliveries from Yale, and several incidents of covert (and deadly) intelligence gathering.

At least two of Capone's driver/bodyguards disappeared, kidnapped and forced to divulge information on Capone's daily schedule before they were killed by Weiss gunmen. A chef from Capone's favorite Italian restaurant was killed after he refused to put prussic acid into Capone's food. Weiss was determined to track the increasingly reclusive Capone's daily routines, to get to know Capone's habits.

Three episodes consumed the Spring and Summer of 1926: the April 27th murder of Chicago Assistant District Attorney Bill McSwiggin,1 Capone's retreat to a Michigan hideaway during the summer, and the Capone organization's April-August takeover of the lucrative rackets in the suburb of Chicago Heights.2

The Weiss-Capone war accelerated again in late summer of 1926. Upon his return from Michigan, Capone assigned a hit team,3 led by Louis Barko, the task of killing Weiss and Drucci.4

On August 10th, Hymie Weiss and Vincent Drucci were walking the four blocks from Drucci's rooms at the Congress Hotel  to a 10:00 AM meeting with trustee Morris Eller of the Metropolitan Sanitary District of Greater Chicago at the Standard Oil Building, 910 South Michigan Avenue. Drucci had $13,500 in cash on him-- obviously a political payoff of the kind O'Banion would have approved.

As they crossed 9th Street and walked toward the building's entrance, four men in a car pulled up to a stop in the middle of street, directly across from Drucci and Weiss. They had obviously been following the Northsiders down Michigan Avenue, looking for an opportunity to strike. At least two men began shooting at Weiss and Drucci from the car windows. The Northsiders dived for cover behind a mailbox and parked cars, pulled out their own guns, and returned fire.

Darting and dodging between the cars, Drucci made a difficult target, so Barko and another gunman leapt from the hit car to get a better aim. As bullets flew, innocent drivers screeched to a halt, and dozens of workers en route to their office jobs dived on the sidewalks and watched the gun battle. Finally, as all the shooters' ammo was just about exhausted, police cars began arriving at the scene. Weiss quickly disappeared into the lobby of the Standard Oil Building, and the two attackers who had jumped out of the hit car made a dash for the running boards as the hit car started to speed away from the scene. One made it, but Louis Barko didn't, and was left in the middle of the street as the Capone hit team sped away.

Vincent Drucci ran out to the middle of South Michigan Avenue, gun in hand, and jumped on the running board of a stopped auto. "Take me away, and make it snappy", Drucci ordered the startled driver, C. C. Bassett. At that moment, Chicago police officers surrounded Drucci and arrested him.

 A Chicago Tribune artists' version of Al Capone's gunmen attacking Hymie Weiss and Vincent Drucci in front of the Standard Oil Building, August 10, 1926.

When Drucci was questioned, he insisted that it was a robbery attempt, and he never before seen any of the gunmen who attacked him. He had never heard of Capone, Barko, or even Prohibition for that matter. "It wasn't no gang fight. A stick-up, that's all. They wanted my roll." He also denied that anyone else was with him during the attack, successfully covering for Weiss. Louis Barko claimed his named was Paul Valerie and he was a just spectator who started to run away because he "didn't want to get hit by a stray bullet."

Hit by a stray bullet was one James Cardan, an officer worker witnessing the shootout, who was grazed in the thigh. Despite at least thirty shots being fired there were, remarkably, no other casualties.

Morris Eller was questioned by police, who were getting pretty good at putting two and two together. Eller was indignant. "Why drag me in? Just because some hoodlums want to shoot in front of our offices? It looks like if a cat has kittens in this town Morrie Eller gets blamed for it!"

Mary Weiss, Hymie's mother, showed up at the South Clark Street police station and posted $5,000 bail for Vincent Drucci-- $1,000 for carrying a concealed weapon, and $4,000 for assault with intent to kill. In the end, there would be no complaint, no witnesses coming forward, and, as far as the Chicago police were concerned, no crime. But it was clear to Weiss that Capone had now turned his full attention to the Northsiders.5

Weiss and Drucci immediately made plans to retaliate. Their extreme response illustrates how out of control the Northside-Capone war had become, and how ineffectual the police were in maintaining even a facade of law and order. New York City gangster Lucky Luciano, no stranger to gunplay and murder, was amazed at what he found during a visit to Prohibition Chicago: "A real goddamn crazy place! Nobody's safe in the streets!"

In a scheme that had Vincent "The Schemer" Drucci written all over it, the Northsiders struck back on September 20, 1926.

From the intelligence he had gathered from kidnapped Capone bodyguards and drivers, Weiss knew Capone liked to stop at the Hawthorne Restaurant in Cicero, the town abutting West Chicago that Torrio and Capone took over in 1923. Along the 4800 block of West 22nd Street, a eighty-foot wide boulevard with two streetcar tracks and two-way traffic, were hotels, offices, banks, stores, and throngs of people shopping or in town for the opening of the horse racing season at nearby Hawthorne Park. The Anton Hotel, operated by Capone's organization, was on the block.

On Monday September 20th, Al Capone and one of his toughest bodyguards, Frankie Rio, sat together at a back table in the Hawthorne Restaurant, facing the front door for the obvious reasons of security. The place was full, with an estimated 60 people at the tables and lunch counter. No doubt Capone had his usual complement of perimeter security people stationed in the restaurant and outside.

With a pre-arranged signal (probably a Northsider operative in a phone booth amid the throngs of people on the sidewalks), a single speeding car raced down 22nd Street at 1:15PM, toward the Chicago city line two blocks away. It looked like a police flivver (car), with a mounted gong clanging loudly in the manner of 1920s police cars. When the sound of machinegun fire was clearly heard, Frankie Rio pulled Capone to the floor and reached for his gun. But as the car sped by the Hawthorne Restaurant, a Thompson machinegun chattering away through a window, there was no evidence of any damage-- no shattering of hotel or restaurant windows, no splattering of lead against building walls or sidewalks. Nevertheless, patrons in the restaurant headed for the back exits or hugged the floor; as the car sped off, some started to get up to peer out the windows.

Capone got up, brushed himself off and started to go the front door to see what the hell happened. At that moment, Frankie Rio earned his pay that day as Capone's bodyguard. In a instant, the amazing Rio realized what had really happened. He yanked Capone back to the floor, pulled him under a table and laid on top of him. Rio's awareness of what was going down saved Capone's life.6 The "police" car was firing blanks, its purpose was to bring Capone to the front entrance, out in the open.

Driving slowly east down 22nd Street, ten more cars now came into view. As the automobile caravan crept past the Anton Hotel, an eruption of machine-gun, shotgun and automatic pistol fire erupted from the passenger side windows of the lead cars. The surreal line of cars crept along, each stopping briefly directly across from the Hawthorne Restaurant. The continuous gunfire intensified as the front of the restaurant was simply shredded, stitches of .45 caliber steel-jacketed machine-gun bullets criss-crossing at waist level, dissolving the front plate glass windows, going through walls, tearing up tables and chairs, disintegrating cups and plates and splattering into the back walls.

Frankie Rio, gun still clutched in his hand, hugged the floor with Capone as dozens of other restaurant patrons and workers did the same. The sheer ferocity of the attack was so overwhelming, there was no thought of fighting back; the only thought was of survival. Capone certainly had more of his personal bodyguard in the area, but not one shot was fired back at the Northsiders.

Suddenly, the gunfire stopped. From the ninth car in the line, a back door opened. George "Bugs" Moran, dressed in a khaki shirt and brown overalls, calmly stepped out of the car as if he were on his way to yet another dull court appearance in front of Judge Lyle. Cradling a Thompson submachine-gun, Moran strolled over to the front door of the Hawthorne Restaurant as a team of other gunmen alighted from the tenth car with shotguns to provide cover.

Moran slowly knelt down at the restaurant's front entrance, poked his tommy gun in the door and fired off a 100 round drum in ten seconds. Moran calmly stood up, turned around and strolled back to the rear car. The shotgun cover team waited for Moran to enter the car, then they followed him. The driver of the rear car hit his horn three times and, with that, the incredible caravan sped off toward Chicago.

Police investigating the scene later estimated over 1,000 rounds had been fired.7 The hotels, restaurants, shops, and some thirty-five parked cars were tattooed with bullet holes. Most amazing of all, no one was killed and only four people were wounded.

The ubiquitous Louis Barko, whom Capone had sent out to kill Weiss and Drucci six weeks prior, was about to enter the Hawthorne for a meeting with Capone when the shooting began. Barko was hit by one round in the shoulder and survived. Sitting in their car in front of the Hawthorne, the Clyde Freeman family, up from Louisiana for the start of the race season, was caught in the firestorm. Their automobile was ventilated front to back,  Freeman was grazed in the knee, his five year-old son, Clyde Jr., had a superficial head wound, and Mrs. Freeman was hit in the arm. Splintering windshield glass also hit Mrs. Freeman in the right eye.8

The aftermath was a matter of the usual suspects for the police. Chief of Detectives William Shoemaker had Barko brought to a police line-up to view Hymie Weiss, Vincent Drucci, George Moran, Peter Gusenberg, Frank Gusenberg, and Henry Gusenberg (all brothers and all Northsider gunmen). Barko, who had to have seen any number of Northsiders during the incident, was true to his gangster credo: he couldn't identify any of them. At the line-up, Drucci might have made eye contact with Louis Barko and smiled-- Barko had repaid Drucci for his own non-identification after the Michigan Avenue shooting.

Capone was shaken, and he must have also felt profound professional embarrassment. The Big Fellow, who took over Johnny Torrio's million dollar a week criminal empire and nearly doubled it, who was the boss of the Chicago outfit, who drove around town in an armored limousine with ten to fifteen bodyguards surrounding him at all times-- left cringing on the floor of the Hawthorne Restaurant while Hymie Weiss and his pals shot Cicero to pieces.

Capone's next move was typical of the man's complexity-- Capone called for a truce and an immediate meeting with Weiss.9

Tony Lombardo, Capone's personal pick now in charge of the influential Unione Sicilione, contacted Weiss and set the date and the place10. The meeting was on October 4, 1926, either at the Sherman Hotel or at the Morrison Hotel (historical sources differ). It is very likely a ranking Chicago police official was in attendance to mediate and to ensure order. Lombardo explained to Weiss that Capone would not be in attendance, to avoid any personal conflicts.

Capone's message to Weiss was simple: "Let's stop the gunplay and get back to the business which has made us rich." Certain that Weiss would eventually kill him, Capone was living in mortal fear every day and he wanted it to stop. He offered Weiss and the Northsiders the uncontested ownership of all liquor distribution north of Madison Avenue-- a generous concession that would ensure Weiss a base of tens of millions a year.

There is good reason to believe Hymie Weiss was more than willing to work with Capone for the sake of business, but Weiss had one piece of unfinished business with Capone-- avenging his mentor and friend, Dion O'Banion. Weiss apparently told Lombardo that he had one non-negotiable demand before any peace could be declared: Capone must give up John Scalise and Albert Anselmi, the shooters who killed O'Banion.11

When Lombardo reportedly called Capone from the hotel with Weiss' bottom line, Capone replied tersely, "I wouldn't do that to a yellow dog!" With that answer, Weiss and his contingent angrily stalked out of the hotel, and any chance for peace died.

Sometime after the Cicero raid, in late September or early October, two seemingly unrelated tenants rented separate Chicago boarding house rooms, one on North State Street, and one just around the corner on West Superior Street. Both locations happened to be in the neighborhood of Weiss' Northsider headquarters.

This would set the stage for the final act between Capone and Weiss.