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 Ten Myths
Part III 10 Questions
   (and 10 answers)



Photo Gallery






1. But one aspect of the O'Banion killing would be put to use again and further expanded-- second and third tier participants in the hit whose overall contributions are not readily evident. These participants provided intelligence, back-up to the primary team(s), and they also ran interference after the hit went down. Although Mike Genna, Albert Anselmi, and John Scalise were the primaries in the O'Banion killing, they were not the only Torrio personnel involved. After Angelo Genna gunned his nickel-trimmed Jewett away from Schofield's on November 10, 1924, six other autos blocked the adjacent blocks of State Street and the intersection of Superior after Genna sped by. It would be illogical not to also assume there was at least one cover car, positioned across from Schofield's next to Holy Name Cathedral, filled with Torrio gunmen ready to blast anyone following the hit team out of the flower shop's front door.  Back

2. See the St. Valentine's Day massacre section of this website.  Back

3. Landesco's very scholarly "Organized Crime in Chicago" (p183) focused on a critical aspect of Northsider security: "The following comments were made by a Capone gangster at the time of the machine-gunning of Hymie Weiss and his companions after he had refused to make peace: 'Do you suppose anybody could lay plans for weeks in advance and establish a machinegun nest that close to Capone's headquarters to get him?
'In the first place, Capone's men are loyal to him. They are willing to lay their lives down for him at any time.' [But this was also the case with the Northsiders]. 'In the second place, he [Capone] is never without a bodyguard. I was away from him for a while and tried to come in to see him. I had to pass a double line of his men and was not allowed to come in until after Mops [Tony Volpe], who knew me well, got permission.'"

O'Banion and Weiss had the money and resources to protect their operations, and provide sufficient personal security, but it seemed to have never occurred to them. The cost for the room at 740 North State Street was $8.00 a week-- that's $416.00 a year. Had Weiss simply bought the building for his staff, he would have created a secure security perimeter for his State Street headquarters. 

4. Daylight savings in the United States was first instituted during World War I. After it was made law, Congress overturned it, and President Wilson's subsequent veto (in his attempts to keep it nation-wide). Certain areas of the country, however, kept daylight savings, including Chicago, and most other large urban areas. So sunset on October 11, 1926 in Chicago would have been at about 8:00 PM.  Back

5. Although Nitti had some staff at the locations for seven days, perhaps noting Weiss' patterns of behavior and daily schedule, the actual time periods when gunmen were at the windows and ready to fire weapons were probably quite narrow. It is illogical to think the teams would wait in the blind for hours and days and then somehow be prepared to react for the two minutes it would take to see Weiss drive up, leave his car and enter Schofield's. But this is exactly how the Weiss killing has been presented in virtually every historic account.  Back

6. The FBI, under Director J. Edgar Hoover, chose not to recognize the fact there was organized crime in America. Hoover, appointed Director in 1924, immediately engaged in petty bureaucratic in-fighting with the Federal agency assigned to enforce Prohibition.
As he slowly comprehended how deeply Prohibition had corrupted America, Hoover realized how incredibly difficult it would be for the Bureau to tackle a problem as big as the Mafia and organized crime. The level of criminal corruption had compromised American urban criminal justice institutions to the extent that Hoover knew his own Agency would also be corrupted in the fight. So, he chose to ignore it for twenty-seven years-- from 1930 to 1957. Instead, J. Edgar Hoover put his FBI resources into the "fight"  against individual 1930s  Mid-western bank robbers and used the national and local press to shamelessly highlight FBI "successes" in the fight against crime in America.
When questioned, Hoover actually claimed there was no such thing as organized crime in America. In 1957, Hoover was finally forced to acknowledge the existence of the Mafia after the Apalachin, New York Mafia families' meeting exploded onto the front page of every newspaper in America.

7. It has always been curious to me that the FBI and organized crime historians have so easily believe the words of sociopath murders and racketeers, whose alcohol and drug ingestion was only surpassed by their congenital lying. Criminals, especially organized crime figures, have a fascinating perspective, but it is one  that is not intellectually validated; the information they produce cannot be subject to any legitimate confirmation.  FBI agents-turned-authors in the 1970s thought they had struck gold when they used the information gained from Chicago mobster telephone tape recordings to finally "discover" organized crime history. The problem was, virtually all of it was untrue.  Back

8. So when Tony Accardo, Capone gunman and later head of the Chicago mob in the 1950-60s, claims to have been a part of the Weiss hit and the St. Valentine's Day massacre, he may well have been a peripheral participant in both hits, but he certainly was not a shooter in either. Again, bugged telephone tape recordings of boasting American mobsters are hardly validating sources of historical fact.

9. Witness statements taken together described the route taken by the gunmen fleeing from 740 State. In retracing their steps, the police found the machine gun in the backyard of 12 West Huron Street.  Back

10. If Weiss, or other members of his group survived or fought back, this team would step in. It is also not improbable that this "third team" drove to the intersection and made a left turn up Superior, perhaps firing a number of rounds at Weiss' party as they went by.  Back

11. Vincent Drucci would succeed Weiss, but for less than six months. Arrested by Chicago police for his fixing activities during the April 1927 city elections, Drucci fought with a young policeman in the back of a squad car. Drucci was shot three times and died before he reached a hospital. George "Bugs" Moran inherited control of the Northsiders, and throughout 1927 and 1928, would take Capone on, in a rather amazing display of gunfire and alliances with other disaffected gangs.
In retrospect, Capone would get few carefree moments from the unending succession of aggressive Northsider leaders. From the day Dion O'Banion was killed to the moment the St. Valentine's Day massacre began his final slide into Federal Court, Capone was always a hunted man. 

12. During the inquest into Weiss' death, October 13-15, a number of truly odd moments occurred. Called as a witness, Mr. C. E. McKibban of 730 North State Street swore that Peller and Jacobs fired at Weiss, and that Weiss fired back at them. He also said he saw O'Brien run over to Weiss' body and remove something from one of the coat pockets.
At the hearing, Weiss' brother, Fred J. Weiss, made the following statement: "I saw him [Hymie] only once in 20 years. That was when he shot me three years ago." And this was at a Weiss family reunion.
Sam Peller was brought to the inquest on a stretcher, but he refused to testify. Benny Jacobs appeared with his foot in a cast and on crutches. William O'Brien testified he was meeting his wife and happened to be in the neighborhood when the shooting broke out.
Finally, Deputy County Coroner Kennedy asked Coroner's Physician Dr. Springer about the wounds on Paddy Murray's body. "We could tell better about such things if the bodies were left alone and the Captains were not so dumb!"
Predictably, no one was arrested for the murder of Hymie Weiss, although newspapers reported the Chicago police were interested in questioning one Frankie Diamond. Another incredible example of the ineptitude of a leaderless police force thoroughly on the take.

13. A witness testified seeing two men burst out of the back windows of 740 State Street just after the shootings; one thirty-five years old, carrying a machinegun, and a younger man holding two pistols. This fits Nitti and McGurn perfectly. Nitti was 38, and Capone did not employ a large number of gunmen in  the 35-40 age demographic-- most were in their 20s. It would also be logical for Nitti to transport (and eventually dump) the machinegun, while McGurn (the more proficient gunman) would be free to have his handguns out and ready for action as the two fled.  Back


October 11, 1926 - Part II

   How did Capone set up the Weiss killing? To whom did he assign the planning and execution of the hit, and what actually happened in front of Schofield's that October afternoon?

Much like the O'Banion hit in 1924, and the St. Valentine's Day massacre in 1929, the State Street ambush was much more complex than it was presented in contemporary newspaper accounts and, later, in books and articles. It involved serious planning, successful coordination, and muchos cojones on the part of the hit teams. Such was Weiss' reputation, all of Capone's people were well aware that anyone who tried to take Weiss out was in danger of not surviving the attempt.

No after-action reports were filed by Capone's hitmen, so there is no insider narrative of what exactly went down. FBI wiretaps recorded thirty and forty years later of Chicago outfit higher ups (during the 1950s and 1960s) reflect more the drug and alcohol macho boasting of old men trying to impress each other (and the FBI agents they sometimes were hustling). 1920s Chicago newspapermen rarely speculated beyond the police party line, and generally would not name specific suspect names unless the Chicago police put the names out there first.

But, by analyzing other operations staged by Torrio and Capone, and by understanding who in the Capone stable was favored at that particular moment in time, we can reasonably piece together the scenario and the players. But in the end, it's all theory.

After the September 20th assault on Cicero, Capone gave the order to set up a final hit on Weiss, which occurred 21 days later. There are three individuals whose stars were shining particularly brightly in the Capone universe in late September of 1926: Frankie Rio, who saved Capone's life in the Hawthorne Restaurant; Frank Nitti, who had risen quickly to become one of Capone's most trusted bodyguards and strategists; and Jack McGurn, whose dapper dress, athletic abilities, and proficiency with many weapons created particular dash and style in the otherwise dull gray world of gangland Chicago.

Frankie Rio was a brain-dead thug-- loyal to a fault, able to complete singular tasks and to put his own life on the line. He could kill and think like a killer-- but planning, execution and follow-through were not in his portfolio. Rio's moment of glory was saving Capone's ass in Cicero, and for that he would be amply rewarded with the Big Fellow's loyalty and largess. Rio was the Luca Brasi of the Capone outfit.

McGurn was on the rise, but he was young and relatively untested. In 1927-28, he would make his bones solo, by being assigned the task of stopping a series of assaults on Capone by the Joe Aiello-Northsider combine. McGurn's dramatic killing successes, and the fact that he quickly became a primary target of George Moran's Northsiders,  convinced Capone to later entrust McGurn with the final solution to the Northsider problem. That would be the St. Valentine's Day massacre.

Frank Nitti had a remarkable history. Originally from Italy, Nitti gained a trade in New York City as a barber who increasingly conducted a side business in stolen goods. Through his New York gang connections, Nitti quickly hooked up with the Torrio-Capone outfit, and, once in Chicago, appears to have been involved in everything from fencing stolen property to procuring Canadian whiskey. He did his time in the trenches in Cicero for Torrio when he and Capone took that town over in 1923. Nitti separated himself from the pack with a rare personal portfolio: intelligence, a proficiency for business  coupled with a facile ability to come up with solutions and alternatives, and a serious talent in the use of a variety of firearms. Nitti and McGurn were the only two outfit members to accompany Capone as bodyguards when he fled to his Michigan retreat in the summer of 1926.

In retrospect, only Frank Nitti had the position, the ability, and the momentum in September of 1926 to be given the critical task of killing Hymie Weiss. It would have been logical for Capone to turn to the thirty-eight-year-old Nitti, no doubt with several critical constraints: the Big Fellow would have had input and veto power over Nitti's choice of staff, and Capone would have demanded daily reports to closely monitor Nitti's progress throughout the assignment.

Nitti took a decidedly different tack in solving the problem of hitting Weiss. O'Banion's killing was a classic up-close in-your-face mob hit, a tactic which had little likelihood of success against the fierce Weiss.1 Nitti had to come up with a new approach.

As we will see later, the St. Valentine's Day massacre, commonly attributed to a five man hit team and two lookouts,  was similar to the O'Banion and Weiss hits --times ten-- as far as the actual number of Capone personnel involved. The numbers of those involved in every major assassination during that period have been historically underestimated.2

Frank Nitti's method was analytical and thorough. He was aware of the Northsiders' complete lack of a personal security system for Weiss.3 Weiss came and went with a loose entourage of drivers, bodyguards and hangers-on. That meant Nitti could work deep within Northsider territory as part of a long-term operation that would not simply take a chance on running into Weiss at the right time-- Nitti's teams would actually track Weiss until he was at the exact place, at the right time, needed to successfully execute the hit.

The initial approach was elemental: somehow cover the front and back doors of Schofield's Flower shop, the one logical place to tag Weiss. So the boardinghouse at 740 North State and the apartment at 1 West Superior were ideal. 740 covered the street in both directions, right up to the flower shop's front door. #1 West Superior covered the intersection of State and Superior, and the alley into which Schofield's back door emptied.

Next, Nitti set up spotters to track Weiss-- an easy task at this point in time, because Weiss was at the Saltis trial virtually every day. This was an era when communications consisted of personal contact or use of random telephones in residences and scattered telephone booths. So this aspect of the project took serious effort. Luckily for Nitti, a large staff on payroll was one of Capone's major resources.

Nitti operatives at the courthouse would either telephone the rooming houses at Schofield's when Weiss was leaving, or they would signal a car waiting outside the courtroom to crank over to West Superior and State and give some kind of high sign to the hit teams. In 1926, most Chicago rooming houses and apartments did not have individual telephone service in each room. If a building even had service, it would most often be via a receiver placed on a hallway wall. Multi-floor buildings might have a single telephone on the main floor.

Without knowing the exact layout of the two buildings used, it is more reasonable to assume Nitti set up a relay between the courthouse and Schofield's. A man sitting in the back of the courtroom would see court was about to be out of session. He would quickly go out front, signal another man sitting in auto on the street, who would in turn speed over to the intersection of State and Superior and honk the car horn as a signal. The hit teams would put down their wine, food, and cigarettes and prepare their weapons and ammunition.

During the seven days Nitti had the ambush rooms set up, there must have been glitches and missteps. His people at the courthouse didn't get word back to the hit teams in time, Weiss didn't go directly back to Schofield's after court ended, Weiss' car parked directly in front of Schofield's, so the hit teams couldn't react to whomever left the car and got though the front door. Maybe there were too many people (or cops) on the street at times, maybe delivery trucks blocked a view, maybe there were weddings and other religious events going on across the street at Holy Name Cathedral.

Given that the Weiss hit could only occur in daylight hours, and given that his daytime schedule was centered on the Saltis trial, it would be reasonable for Nitti to presume the hit would go down between the time court ended its session (3-4 o'clock) and sundown (around 8 o'clock4). So the actual window for the ambush would be a five hour period between 3:00 PM and 8:00 PM (and in reality, the plan may have simply centered on intercepting Weiss immediately after court ended, a 30 minute window). This would allow Nitti to schedule his best people to the ambush locations when it was most likely to go down.5

Whatever the case, at four o'clock on October 11, 1926, everything came together. Nitti had plotted carefully, taken his time, and constructed a scenario with multi-layered, low-failure high-success elements. Since the teams must have stood by numerous times while Weiss came and went, Nitti also obviously kept a strict hand on his people being too trigger-happy-- not the easiest task given the people involved.

Over the years, many names have surfaced in speculation of who exactly were in those rooms at State and Superior. When the FBI began seriously wiretapping members of the Chicago outfit in the late 1950s and throughout the 1960s, they had little history and context for the miles of taped conversations which had to be analyzed.6 At the time, the mob was run by men in their sixties, a number of whom had worked for Al Capone in the mid-late 1920s; men who often bragged about themselves and casually reinvented their resumes to impress each other, those working under them, and FBI agents listening to their conversations.7

On the other hand, the high-profile incidents of the 1920s booze wars often involved more participants than era newspapers and later historians represented. In the case of the Weiss hit, we are talking two or three gunmen in each room, signal callers at the courtroom, back-up teams, lookouts, etc. Although maybe six-eight men were involved in the actual hit when it went down, over a dozen must have been involved in the overall project.8

Nitti would have asked for, and received, Capone's best people at the time. That short list would start with Frank Rio, John Scalise, Albert Anselmi. Jack McGurn, Frankie Diamond, Tony Volpe, Louis Campagna, Sam Hunt, and Phil D'Andrea. These were classic tough, Italian and Sicilian mob gunmen, the majority of whom had multiple notches on their guns and were dedicated to the Big Fellow's service.

How many of Nitti's hand-picked gunmen were at the scene of the Weiss hit when it occurred, and what were their names?

Oddly enough, it is easier to suggest who was involved in the more complicated St. Valentine's Day massacre than who directly participated in the Weiss hit. St. Valentine's was a linearly executed set-piece, whereas the State Street ambush involved a time/place continuum with the potential of at least two, and probably three, hit teams shooting at the same time. While no one can finally document the shooters at Weiss' killing, we do have evidence and testimony from the police investigation and from the inquest.

There were two men in the windows of 740 State Street firing weapons. One person was firing a Thompson sub-machinegun and the second was firing an automatic shotgun. Thirty-five .45 caliber shells and three shotgun shells were later found on the floor of the room at the windows. Immediately after the shooting, witnesses saw two men crash out of a first floor window and into the alley behind the rooming house, and run up the alley towards Superior Street. The number of shots fired is unclear, since we don't know if any magazines or spent shells were hurriedly scooped up after the firing stopped.9

There were two men at #1 West Superior Street-- but did they fire during the hit? An unfired shotgun was found at that location a number of days after the ambush. While this team's assignment was to cover the back alley behind Schofield's, they also had an unobstructed view of the intersection of State and Superior. I found no mention of spent shells at this location, so it has been presumed this team did not participate in the killings. But this is not proof the second team didn't fire their weapons.

There were also two eyewitness accounts of at least one auto speeding north past the intersection, its passengers firing on Weiss' party.10

So what actually happened?

The hit teams knew Weiss was coming back from court and they were waiting for him. After his car parked, the gunmen at both locations held off until Weiss and his party were crossing the street directly to the right front of the second floor windows at 740 State Street. The team at 740 State opened fire, the team at #1 Superior may not have fired, and escaped soon after the incident. It is not improbable that, given that there was full warning of Weiss' arrival, there was at least one back-up team in an automobile parked somewhere on State Street (probably just south of Superior).

Much was made of the fact that days later police discovered the second ambush nest and found a golf bag with an automatic shotgun inside at #1 West Superior. Sam Hunt, one of Capone's top shooters, was so well known for carrying his weapons around in golf bags, his nickname became Sam "Golf Bag" Hunt. This evidence puts Hunt as one of two gunmen at #1 Superior (maybe with Frank Rio).

Between 1926 and 1929, George Moran took over Northsider leadership after Weiss and Drucci were killed.11  During Moran's reign, one member of Capone's outfit was particularly singled out for repeated Northsider assassination attempts: Jack McGurn. Since the Northsiders placed "personal scores to settle" on a higher par than regular gang business, there had to be an very important reason for repeatedly targeting McGurn. That logic, then, makes McGurn one of two hit team members inside the boardinghouse room at 740 State Street.

John Scalise and Albert Anselmi rarely missed participating in an important Capone outfit hit during the 1920s. Evidence seems to show that, at the time of the planning and execution of the Weiss hit, the "murder twins" were stuck in Joliet State Prison, serving the first months of a 14 year sentence for the murder of Chicago Police Officer Olson (during the Northsiders' abortive 1925 hit attempt on Mike Genna). A re-trial, and yet another trial from the same incident, ended in a "not guilty" verdict on June 23, 1927. Strike Scalise and Anselmi from the hit teams.

The back-up car of gunmen on State Street could have been any combination of Capone gunmen. Tony Volpe, Louis Campagna, and Frankie Diamond all must of had the opportunity to be part of the ambush. No doubt this team found it irresistible not to get involved and take a couple of shots as they drove away. Witnesses at the inquest described several other sources of gunfire during the ambush.12

For the second of the two gunmen in the second floor room on State Street, there are any number of choices. But one man had partnered up with McGurn to protect Capone when he spent the summer of 1926 hiding out in rural Michigan. A serious bond probably developed between the two, as they were tasked with the heavy responsibility to protect Al Capone during the time he was actively being hunted by Hymie Weiss.

That same man organized the entire Weiss hit, and would feel an irresistible need to be there when the hit finally went down. I believe Frank Nitti put himself into the ambush as an active participant. Planning the hit was one thing, but many of the people involved in the Weiss hit had already "made their bones" in previous action. This was Nitti's chance to finally be made.

Jack McGurn fired the machinegun and Frank Nitti the shotgun during the Weiss hit. After this incident, both men's careers soared in Capone's galaxy, and for good reason: They were the men who killed Hymie Weiss.13



Earl "Hymie" Weiss lies on the Chicago coroner's morgue table hours after his death at Henrotin Hospital (photo used by permission of the Chicago Historical Society). A gunshot wound is clearly seen above his left eye, another wound on the right jaw. His nose appears broken, probably as a result of falling to the street after the first rounds struck his body. The Coroner found both .45 caliber steel-jacked machine-gun rounds and shotgun pellets in Weiss' body.

Weiss was buried in a bronze casket with silver fittings at Mount Carmel Cemetery. The Catholic Church denied Weiss a Mass for the last rites and burial in consecrated ground, as the Church routinely did when the subject was a known gangster. Weiss' boyhood classmates from St. Malachy's school carried his coffin from Sbarbaro's Mortuary to the waiting hearse. At the funeral were Vincent Drucci, George Moran, the Gusenberg brothers, and Albert Weinshank, all veteran O'Banion men. Mrs. Dion O'Banion was there to comfort Mrs. Mary Weiss, and even Frankie McErlane found time from his murder trial to attend. Vincent Drucci now took on leadership of the Northsiders, with Moran's help.

George Moran made no provocative statements about Weiss' death to the Chicago newspapers, but he was consumed with hatred for Al Capone and for Weiss' killers. Moran, his gunmen, and Moran's new-found ally Joe Aiello, would make 1927 and 1928 deadly years for Capone and his people, at a time when the Chicago outfit should have been able to sit back and enjoy the fruits of an incredible criminal empire. Although the Capone organization's 1928 revenues were estimated to be well over $100 million, and despite the fact that ownership of the Chicago police was just another operating side-cost, Al Capone would have to continually look over his shoulder in fear-- for the shadows of the pursuing Northsiders.