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 Massacre
Part I: Overview
Part II: Top Ten Myths
Part III: Ten Questions
(and ten answers)


Photo Gallery






1. There are, of course, no final "answers" to many of the questions surrounding the St. Valentine's Day massacre. I approach each point by using available research to reboot and reexamine traditionally accepted Chicago mob history, by forming logical theories, and by critiquing the theories of others. While I am critical of both the traditional, and more recent, theories that attempt to explain this crime, the great work of current Prohibition Chicago writers, researchers and genre  enthusiasts energize and inspire me. These are some very talented and really nice people.

2. Thanks to the misleading theories fronted off by the Chicago Police Department in 1929, and the ineptly interpreted information concocted by the FBI in the 1930s, and you begin to understand how little official criminal academic research has been undertaken to begin to understand this crime.

3. There is no question that Hoover's negligence in refusing to join the FBI in the fight against organized crime from 1930 to 1960, left the United States of America at the mercy of a dozen national crime families whose rackets plundered and corrupted major cities and basic societal institutions for decades.
It is a tragically sad and pathetic chapter in the history of the Federal Bureau of Investigation.

4. Every generation seems to have similar shocking moments: the sinking of the HMS Titanic in 1914, the Japanese attack on Pearl Harbor in 1941, the assassination of President John Kennedy in 1963, the murder of 3,025 Americans on 09.11.01 by religious fanatics; these are ultimate historic examples of individual and collective unexpected death on a scale that literally turns societal life upside down. The psychological effects are fear, disorientation, and loss of faith. Irrespective of the actual loss of life, the impact of each event at the time it occurred was an emotionally powerful shock across the nation.

5. The Aiellos survived the 1925 destruction of the Genna empire in large part because a) they were not involved in the O'Banion killing (so Weiss wasn't hunting them down), and b) Joseph Aiello's partner in the sugar business was Tony Lombardo, a Sicilian allied with Al Capone (so Capone wasn't hunting them down).

6. The cover story was that representatives of a deeply concerned Joe Saltis requested the meeting, in light of Capone's discovery of the emerging Saltis/Northside alliance (seemingly making the temporarily incarcerated Saltis the next logical target). But it is hard to believe the elite of Chicago gangsterdom would breathlessly rush to a peace conference called on behalf of southside pugster Joe Saltis.

7. According to author Kenneth Allsop, George Moran was in no mood to sit down with Capone. Apparently, Vincent Drucci convinced Moran to attend the meeting in the name of business. Back

8. Some newspaper accounts of the time stated gunmen who were hunting each other down like dogs only days prior, sat together at tables sharing carafes of rich chianti, while exchanging colorful stories of prior mayhem over plates of fettuccini bolognese. Yet another example of silly gangland history cooked up by jaded Chicago crime reporters and era writers.

9. As author John Binder points out, the term "the Outfit" was first used in the early 1950s as a proper noun identifier of the Chicago mob created by Torrio and Capone.

10. The actual cease-fire period lasted all of seventy days-- eventually old rivalries and new territorial disputes led to a renewed interest in the use of deadly force. But by then, Capone's world was even brighter: Weiss' Northside partner, Vincent Drucci was dead, and the Big Fellow's chosen candidate for mayor of Chicago, William Hale Thompson, was elected, in April 1927 (in large part due to Capone's quarter of a million dollar campaign contribution, as well as the usual excellent turn-out by deceased Chicago voters).

11. Aiello's approach was bold, foolish, and crazy all at the same time- in retrospect, a roadmap followed by any number of Chicago Prohibition gangsters. In the end, the Aiello-Moran combine came much closer to achieving their goals than genre authors have previously presented. Joe Aiello suffered a number of serious defeats, achieved several  significant successes, and was run out of Chicago twice during the next four years-- only to come back each time. Give Aiello credit for nerve, persistence, and incredible Sicilian cajones for even attempting to take on the Capone empire and its cadre of killers in 1927; but, at the time, the Outfit was simply too big, too wired, and virtually too untouchable for even bold independent entrepreneurs to crack.

   Joe Aiello

12. Antonio Torchio from New York City, on May 25, 1927; Anthony Russo and Vincent Spicuzza from St. Louis, and Sammy Valente from Cleveland, and probably unknown others, each met a bloody fate.
Author Kenneth Allsop documents that, during the same period (in a six week stretch), roving Capone gunmen also eliminated six members of Aiello's gang: Lawrence La  Presta on June 1st, Diego Attlomionte on June 29th, Numio Jamericco and Lorenzo on June 30th, Giovanni Blaudins on July 12th, and Dominic Cinderalla on July 17th.

13. Take a minute to think of your own immediate wish list and goals for career and personal advancement and your approach to achieve them. Then contemplate Mr. Aiello and Mr. Moran, as they faced a monster criminal organization that generated a hundred million dollars a year, had an elite killing machine on its payroll, and literally owned numerous elected officials, police, and members of the media. What unique combination of craziness and bravado would it have taken anyone to decide, why sure, let's take on the monster Al Capone and see what the hell might happen?

14. That organization's impact on Chicago politics and city government, and its exclusive hold over Sicilian immigrants, was finished. The illegal money and influence gained from Prohibition by organized crime completely overwhelmed not only the legal institutions of the city of Chicago, but every institution in the city: the media, the church, the  Unione, the police, local and state elected officials, everything.

15. In business, a CEO would address point #1 by firing, demoting, or promoting people-- sometimes arbitrarily just to shake up the organization and move younger people into the mix. This is Big Business 101.  Another tack would be to either expand marketing and influence by buying other companies, or cashing in assets by selling components that would solidify the organization's base.
A top CEO would deal with the second issue by allowing the brightest of his executive staff to run with their new ideas, and go forward with their solutions to current problems. This type of empowerment buys deeper loyalty at (usually) very little risk. And if the up and coming execs devise a better mousetrap, or they actually solve a current problem, so much the better.


St. Valentine's Day Massacre
Part I: Introduction

Few crimes in history have generated the sense of terror and outlaw outrage as the St. Valentine's Day massacre. Al Capone, the first American gangster to achieve world-wide celebrity, took his brutal image into the permanent historic continuum in a wash of blood in Chicago on Saint Valentine's Day 1929.

Given the hundreds of versions of this incident published and filmed during the past seventy-nine years, there is little need to add yet another dramatic retelling of the same tired story. I will, instead, present a series of myths and pose a series of questions about the crime; myths that, in the constant retellings over the years, have come to be accepted as truth, and questions I have asked (and answered) as a researcher in determining the "why", "how", and "who" of this classic crime.1

The purpose of this section of the website is to attempt to strip away the painted layers of accumulated historical stories, assumptions and rumors which quickly became part of the unshakable biblical cannon of the massacre. Thanks to the inept investigation of the crime conducted by the Chicago Police, and decades of carelessly researched published accounts, whole sections of the St. Valentine's Day massacre story were fabricated and invented, often simply for the sake of added drama.2

Some of the basic "truths" of the St. Valentine's Day massacre, taken for granted over the years, were simply cooked up by newspaper reporters over drinks, or fed to them by pontificating ranking members of the Chicago PD. More times than we might like to concede, this is exactly how a great deal of Chicago Prohibition history has been conceived and presented as fact. 

The theory of legend allows that the more frequently any statement is repeated in any mass media, the more that statement assumes the appearance of truth. Ask any newspaper or television news reporter.

Following a series of top ten myths about the crime, I will pose, and attempt to answer, a series of critical questions about the St. Valentine's Day massacre. For my fellow researchers and enthusiasts, let your blackberry go blank, take four steps back, and have another glass of red wine; the major misconceptions about how and why this crime was committed are virulent and epidemic.

More recent evidence about the massacre published in various articles and books during the past several years are primarily based on two sources: FBI wiretaps from the late 1950s and 1960s--  ridiculous and embarrassing source material garnered from the substance-assisted posturing of Chicago mob bosses, and the sad gullibility and inexperience of J. Edgar Hoover's FBI. The informal FBI "investigation" into the massacre was essentially information dictated by a single criminal informer in 1935, who later changed critical parts of his story.

Concocting a pretense of fighting crime in the 1930s by chasing a series of Midwestern bank robbers, and later tracking down phantom American communists and compiling damaging dossiers on powerful American politicians and celebrities, FBI Director Hoover publicly denied the existence of organized crime in America for thirty years. When finally forced into admitting the existence of the mafia in the late 1950s, Hoover's inexperienced agents focused on the Chicago mob, and eagerly swallowed the macho bullshit and calculated disinformation fed to them via miles of illegal wiretaps. Certainly, the FBI of the 1930s was in no way interested or capable of understanding any organized crime information being fed them by petty criminals.3 


Just what was the St. Valentine's Day massacre?

On a chilling and snowy winter morning on February 14, 1929, five Northsider gangsters, their vehicle mechanic and a civilian hanger-on were machine-gunned and shotgunned to death inside a Chicago garage. In the midst of the jazzy 1920s, this singular incident froze the nation's soul. For the time, the impact of the slaughter was similar to those devastating moments in history which challenge the safe reality of everyday living; an incident so searing on the collective psyche that basic life values are shaken.4

Newspaper coverage and radio commentators didn't have to induce outrage and shock over the St. Valentine's Day massacre; people in Chicago and throughout the country were disgusted and offended. The Prohibition gangster shootouts, the celebrity of Al Capone, the excitement of machine-guns and bootleggers had been a kind of decade-long pop entertainment-- real life comic-strips one could follow daily on the front pages of the morning newspapers. All of a sudden, the experience turned bloody brutal and ruthless. All of a sudden, gangland wasn't colorful-- it was pitiless and deadly. A line had been crossed.

What was the historical context of the crime?

The historical context of the slaughter was as dramatic as the event itself.

In 1920, Prohibition provided an opportunity for an elite group of gangsters in urban America to conceive a dramatically new method of generating illegal revenue. These criminal visionaries saw the revenue from Prohibition could create criminal combines that would grow beyond the unorganized day-today criminality urban America was used to, into multi-million dollar institutions untouchable by society.  In Chicago, John Torrio and Al Capone turned a local criminal enterprise into a hundred million dollar a year cash cow. Torrio understood the implications of the 18th Amendment to the Constitution better than any United States Senator or Congressman: make the use, sale, and transportation of alcohol illegal in America, and only criminals will pocket the hundreds of millions of dollars beer and hard liquor sales generate each year.

In 1924, Dean O'Banion, the charismatic leader of Chicago's Northsider gang and his organizational genius, Earl "Hymie" Weiss, broke away from Torrio's city-wide booze combine and openly challenged Torrio and his second-in-command, Al Capone. O'Banion was quickly eliminated, but Torrio and Capone soon discovered O'Banion's violent legacy: a cadre of revenge-minded and talented Northsider successors who, amazingly, placed personal loyalty and vengeance above the lucrative criminal business of bootlegging and racketeering.

Earl Weiss was O'Banion's partner and best friend. From the day O'Banion was murdered, a distraught and vengeful Weiss came after Torrio and Capone, and their mega million dollar criminal empire. In the process, Torrio was critically injured in an assassination attempt, which forced history's first crime boss out of Chicago forever. At the same time, Weiss took his own Northside gang's promising enterprise and turned it into a burgeoning criminal combine, pitting Weiss against Capone for total domination of the rackets. Torrio's successor, Al Capone, waged an open war with Weiss, until Capone managed to kill Earl Weiss in 1926.

At first, it seemed Weiss' death might finally bring an end to the war with the Northsiders. Capone feared Weiss more than any other man, and now Weiss was out of the picture; but the legacy of Dean O'Banion and Hymie Weiss would haunt Al Capone, and every man who worked for him, until May 3, 1932, the day Capone was put on a train at Chicago's Union Station, bound for the Federal prison in Atlanta to serve an eleven year sentence for tax evasion.

In the two years following Weiss' death, the deadly tenacity of the Northsiders finally prompted Capone to authorize an act calculated to eliminate Northsider interference once and for all; but it was an act destined also to dramatically accelerate his own downfall: the St. Valentine's Day massacre.

What was the path from Weiss' murder to the massacre?

 Weiss' life-long pal and immediate successor, Vincent Drucci, didn't have a great deal of time to respond to his close friend's killing. Drucci, a hyper "type A" personality, and a deadly gunman, would  live only six months after the State Street ambush-- killed by a Chicago policeman on April 4, 1927. But, following-up on Hymie Weiss' brilliant positional strategy to enlist outside allies in the fight against Capone, Drucci had already begun talks between the Northsiders and another emerging Chicago gang family.

The Sicilian Aiello clan were semi-independents, who made money in the early 1920s providing the Terrible Genna gang with the base ingredients required to manufacture their mass-produced rotgut liquor. Led by Joseph Aiello, eight brothers and dozens of cousins and surviving Genna soldiers slowly took back control of the alky business in Little Italy after Weiss and Capone dismantled the Genna brothers enterprise. Slowly, the Aliello clan began the dangerous crawl back up the Prohibition food chain.5

Typical of the complex, non-linear history of organized crime in America, multiple elements came into play.

Fourteen days after the Weiss killing, a remarkable meeting took place in Chicago's Hotel Sherman. On October 26, 1926, virtually every major gangland heavyweight still standing attended an actual honest-to-god peace conference, literally in the wake of Hymie Weiss' death.6

Capone may have had trouble sleeping at night even after Weiss was killed, imagining psycho-freak Frankie Erlaine on the loose and scalp hunting in support of the next Northsider assault on his empire. As far as the Hotel Sherman meeting, to paraphrase the later George Moran, only Capone calls meetings like that.7 And, true to the peace-not-war mantra of his mentor Torrio, Al Capone likely genuinely welcomed the opportunity to step outside his armored car for a moment and breath the fresh industrial air of a free Chicago.

This most unique peace conference was co-chaired by the Jimmy Carter of the Chicago rackets, Maxie Eisen, and by the suave Tony Lombardo, Capone's personal conduit into the city's restrictive and secretive Sicilian community.8

Eisen supposedly delivered a sage keynote address that set the stage for a remarkable booze war time-out over the next several months: "Let's give each other a break", implored the ever temperate Eisen, surveying some of the deadliest killers in the history of  American organized crime. "We're a bunch of saps, killing each other this way and giving the cops a laugh." Al Capone also allegedly addressed the gathering, saying "We're making a shooting gallery of a great business, and nobody's profiting by it. There's plenty of beer business for everybody-- why kill each other over it?"

But, quickly underscoring his newly minted dominance in the wake of killing Weiss, Capone proceeded to describe just how the city of Chicago would be sliced up, like a plump Thanksgiving ham. There would be modest pieces for each gang attending the peace conference, and some consideration for those absent, but the lion's share went to the Outfit.9

The message of the "peace conference" was clear: Capone is now boss, so follow orders, stop the shooting, and be glad you were given a small piece of the action.10

Unhappy with Capone's modest parcel of two city wards for his group was Northsider George Moran, who actively continued independent talks with the emerging Aiellos, creating an unlikely alliance which would trigger a dramatically reinvigorated assault on Al Capone's cartel. And, true to their Northsider roots, Moran and his henchmen were especially itching to pay Capone's people back for the murder of Hymie Weiss.

Joe Aiello's own grand plan was three-fold: first, cement ties with George Moran and the remnants of the Northsiders, as well as other disaffected gangsters, in preparation for a final takeover of the leaderless Outfit. Second, make the Outfit leaderless-- hit Capone and remove him from the scene. Third, and most critically important, take possession of that cornerstone of Chicago political and rackets power, the Unione Siciliana, now run by Aiello's former partner (and Capone man) Tony Lombardo, by any means necessary.11

After making the initial contacts with Drucci and Moran to explore the possibility of a new alliance, Aiello independently began his attack on Capone the old fashioned way: he simply placed a $50,000 bounty on Capone's head, then informed Sicilian crime organizations in St. Louis, Cleveland, Kansas City, New York and New Jersey about this wonderful opportunity. Soon, a series of out-of-town Sicilian gunmen began arriving in Chicago to attempt to collect that bounty.

But, such was the depth of Capone's organization, and the death-grip with which he held the city of Chicago, each of Aiello's imported Sicilian killers was tailed and killed soon after arriving by train at Union Station.12

Someone was taking care of business for Capone in a big way, and that someone was Jack McGurn. After 1926, as Frank Nitti merged to the strategic planning and business side of the outfit, his partner McGurn became the go-to guy for matters of security and pro-active offensive operations. This would give McGurn an extremely busy day book for 1927 and 1928: first, fighting the Aiello-Moran incursions into Capone's empire, while at the same time finding a large target painted on his rear end by Northsider assassination squads seeking vengeance for his role in killing Weiss.

Joe Aiello's goal was to eliminate Al Capone and take over his rackets; for Moran, the goal was to eliminate McGurn and take as much from Capone as he could get without ending up in a ditch somewhere on the empty plains stretching out beyond the western boundaries of Cicero.13

         And Moran and Aiello paid it forward. On Friday September 7, 1928, Capone's handpicked head of the Unione Siciliana, Tony Lombardo, was leaving Unione headquarters on Dearborn Street with his two elite bodyguards. Northsider gunmen James Clark and Peter Gusenberg stepped in front of the trio in at the corner of Madison and Dearborn, in the midst of what was arguably America's busiest urban corner, and brazenly shot them down. Lombardo and bodyguard Joseph Ferraro fell into the gutter with dumdum bullets to the head and spine, and Al Capone went into mourning. On January 8, 1929, Capone's choice to succeed Lombardo, Pasqualino Lolordo was shot to death inside his Chicago apartment by Joe Aiello, James Clark and Peter Gusenberg.

For Al Capone, these were troubling incidents, but Capone, even in his grief and anger over the deaths of Lombardo and Lolordo, would not be the driving force that brought seven Northsiders into a garage on St. Valentine's Day 1929.

Who devised the crime, and what was it's purpose?

Capone had to be angry over the deaths of his handpicked Sicilian associates in charge of the Unione, but it is critical to understanding the geneses of the massacre that Al Capone would no more have conceived and planned the St. Valentine's day massacre than the CEO of the Bechtel Corporation would take the time to choose the office furniture in the company's Toledo field office. (That is, if Bechtel has a Toledo office.)

Two people proposed and devised the St. Valentine's Day massacre: Frank Nitti, the architect of the successful hit on Hymie Weiss, and Jack McGurn, Nitti's partner and a shooter in Weiss' killing.

As it turns out, McGurn and the final solution to the Northsider problem is a familiar scenario in the institutional matrix of large corporate organizations: the up-and-coming young exec with a recent record of brilliant successes, devises a clear roadmap to solve a current critical problem, pitches his idea to a trusted higher up (Nitti), and both refine the plan and present it to the CEO (Capone). The CEO, pleased that his best people are proactively looking out for the organization, is eager to support and reward them. Capone quickly gives their plan a green light.

But the critical question, long misinterpreted by crime historians, is why McGurn raised his hand to take the Morans out. Traditional history cites only Capone's supposed troubles with Moran: the sinister connection with Aiello, booze shipments hijacked by Moran, the deaths of Lombardo and Lolordo-- Capone's chosen heads of the  Unione Siciliana. But none of these are the real reason the St. Valentine's Day massacre went down.

Again, it's difficult to imagine the day to day management of Capone's empire, and to understand the level of insulation and detachment Al Capone must have had in 1928 from  the outfit's day to day business. The Northsiders hijacking a dozen booze shipments wouldn't have been a blip on Capone's day-to-day radar screen; Lombardo and Lolordo's deaths were troubling, but the reality was that, by 1928, the former power of the Unione Siciliana had seriously dissipated.14

If there was any pressure on Capone to address the Aiello/Moran threat in a more proactive manner, it would have come from within his organization, from below. Capone, as the top CEO of a hundred million dollar combine, needed to demonstrate that, 1) his control of the organization was solid; and, 2) he cared about the problems of his top underlings, even if he was out of touch with their day to day issues.15

Jack McGurn's most pressing problem was that he had became a walking skeet target because of his participation in the 1926 Weiss hit. Even a cursory review of the history of the Northsiders clearly demonstrates their raison d'etre, after 1924: vengeance for the deaths of their spiritual leader, O'Banion, and their organizational genius, Weiss. McGurn's death was the number one priority for Moran's top killers, the brothers Frank and Peter Gusenberg, and James Clark.  Three attempts on McGurn's life between 1926 and 1928, including being nearly machined gunned to death in a Chicago hotel phone booth, moved the destruction of Moran's killers to the very top of McGurn's "things to get done soon" list. No doubt, Frank Nitti, McGurn's former running buddy, shared his pain.

So the scenario was set when Capone empowered his best and brightest, demonstrating that he understood their concern for their own future and for the future of the organization. In 1926, Capone mandated that Nitti and McGurn solve his Weiss problem; in 1928, he provided Nitti and McGurn the authority and resources to solve their Moran problem.