St. Valentine’s Day 1929 began like most other winter mornings in Chicago, with gray skies and stinging cold. A light snow, like confectioner’s sugar, powdered the city’s sidewalks. Bakers and florists woke early to prepare for the crush of holiday customers. All over the city, children put the finishing touches on cards before leaving for school.

Of course, not everyone was engaged in thoughts of loving kindness. Over at the Cook County Jail, guards prepared for the planned midnight execution of three convicted killers. On LaSalle Street, bankers and stockbrokers nervously watched their stock tickers as trading began in New York. And inside a humdrum garage at 2122 North Clark Street, in a quiet residential neighborhood, an unusually large number of hoodlums gathered for purposes unknown.

Except for a single white light bulb dangling from the ceiling, the big garage on Clark Street was dark, the parked trucks and cars almost lost in the vast shadowed spaces. A bit of weak winter sun filtered through the grimy front window. The garage was rented by the George “Bugs” Moran gang, which controlled much of the North Side’s illegal booze traffic and ran most of its brothels and casinos. The garage was used for storage and repairs, not as a hideout or hangout. So there was only one explanation why seven men would be there at an hour when most thugs were still sleeping off the prior night’s intoxicants—and it wasn’t to exchange valentines. They had a job.

With the exception of the mechanic, the men all were well dressed that morning in suits, ties, tie pins, and street shoes. One of them wore a carnation.

Soon they would all be dead, victims of the most infamous unsolved crime in U.S. history, the St. Valentine’s Day Massacre.

The massacre changed everything.

Though Americans had never been very happy with the effects of Prohibition, they weren’t clamoring to do something about it. Prohibition had made millionaire celebrities out of gangsters like Al Capone and turned the nation’s justice system into a cesspit of corruption. But people tolerated the situation because they counted on the bootleggers to get them their booze and because almost

all the related violence was of the gangster-on-gangster variety. But the slaughter of seven men—with gruesome photos flung nationwide in newsprint—proved too much to stomach for many.

The president-elect, Herbert Hoover, had made criminal justice a central part of his campaign. Now, as he vacationed in Florida and prepared for his inauguration, the reverberation of gangland savagery shook the nation. Hoover would take office more determined than ever to clean up this mess. He was a brilliant bureaucrat but also a shrewd public-relations man. So he determined to repair the nation’s criminal justice system and to make an example of Capone, the nation’s most notorious gangster and the man widely believed responsible for the St. Valentine’s Day Massacre.

For all its impact, the full story of the St. Valentine’s Day Massacre has never been told, and most of the world still assumes that Capone orchestrated the attack. Yet new evidence suggests that the crime was almost certainly not the work of the man referred to within his own organization as the Big Fellow and known to the public as Scarface or Public Enemy Number One. Herbert Hoover almost certainly knew that, as did the men in Chicago assigned by the president to get Capone, and their refusal to acknowledge his innocence was one of many reasons the crime went unsolved.

As it happened, the explanation for the massacre may have been much simpler than anyone imagined. It may have been attributable to one of the oldest and surest motives of all: revenge.

But that wasn’t what the feds wanted to hear.

The day after the massacre, a coroner’s jury watched police reenact the killings at the scene of the crime. For more photos, see the gallery »

At around 10:30 in the morning on February 14th, a big black Cadillac turned from Webster Avenue onto Clark Street, heading south. It stopped in front of the SMC Cartage Company at 2122 North Clark Street. Four or five men got out of the car (eyewitness accounts varied). One man, the driver, wore a fancy chinchilla topcoat and a gray fedora. Two wore police uniforms. The wind blew snow dust as they stepped across the sidewalk and into the garage through the front door.

Seven men waited inside. Johnny May, dressed in greasy brown coveralls, was lying on his back under a jacked-up truck, repairing a wheel. He was a former safe-blower hired by Moran as an auto mechanic and one of the countless Chicagoans who could thank Prohibition and the bootlegging business for giving him a good, steady, and relatively safe career. May lived with his wife, his seven kids, and a dog named Highball, who was tied by leash to the axle of the truck. The other six men were milling about, trying to stay warm. There were the Gusenberg brothers, Frank and Peter, two of the city’s most troublesome goons; James Clark (real name: Albert Kachellek), a convicted armed robber and a reputed killer; Adam Heyer, a.k.a. Frank Snyder, an accountant and embezzler; Albert Weinshank, a nightclub owner and a newly appointed official of the Central Cleaners and Dyers Association; and an optometrist named Reinhardt H. Schwimmer, who hung around the Moran boys mostly so he could brag to friends about his underworld connections.

If Moran’s gangsters were frightened by the new arrivals, they didn’t show it. Most of the Moran men were armed. But not one reached for his weapon in time to do anything with it. Maybe they had been expecting the company. Maybe they knew their guests. Or maybe, seeing men in police uniforms, they decided to play it cool. If it was money the officers wanted, Moran’s men had plenty of it.

But this wasn’t about money. The intruders raised their weapons—two Tommys and a 12-gauge shotgun—and ordered Moran’s men to move away from the doors and windows. They lined them up shoulder to shoulder against the wall on the garage’s northern side.

They raised their guns.

In a haze of sprayed machine-gun fire, brick dust, and smoke, seven men fell. Bullets tore through flesh and sinew and lodged in the wall. Shells pinged to the ground and spun. Blood dark as motor oil surged across the cold concrete floor and slid thickly down a drain. Some men died instantly, some gasped briefly for air.

Out on Clark Street, neighbors heard popping noises, which some took for the sound of a backfiring engine. Others heard the desperate howling of a dog. A few peered out of their windows in time to see men leaving the garage and getting into the Cadillac. It looked as if two cops were leading two or three other men, possibly at gunpoint. The automobile sped south on Clark Street, zigzagging to avoid a trolley, and disappeared from view somewhere around Armitage Avenue.

Soon one of the neighbors walked over to the garage and pushed open the door. He spotted mutilated bodies on the floor and inhaled the stench of blood. Smoke still hung in the air. The dog Highball continued howling. Six men were dead. The seventh, Frank Gusenberg, was still alive.

Sergeant Thomas J. Loftus, a veteran of the 36th District station, responded first to the call. After moving a bunch of neighbors away from the bodies, he spotted Frank Gusenberg, shot 14 times but hanging on. “Do you know me, Frank?” the sergeant asked.

“Yes, you’re Tom Loftus,” the gangster said between gulps of air. Then Gusenberg added: “I won’t talk,” as if he knew from experience the copper’s next question.

But after sucking more air, Gusenberg (according to some newspaper accounts) did talk, briefly. “Cops did it,” he said.

Loftus pressed for details but got none.

“For God’s sake,” said Gusenberg, “get me to a hospital!”

He got to the hospital and died there without further comment.

Al Capone in a 1931 mugshot. For more photos, see the gallery »

At the time of the crime, Al Capone sat in a Dade County, Florida, courthouse, wearing one of his fashionable summer ensembles: white flannel trousers, a checkered sport jacket, and a light gray fedora. He was 30, overweight, but still powerfully built, and had a sharply receding hairline. Though world famous now as a villain, he was almost never photographed without a smile.

Capone had come for an interview with Louis Goldstein, a prosecutor from Brooklyn, who was investigating the murder in New York of Capone’s old friend and mentor, Frankie Yale. Capone was so confident that he arrived without a lawyer. But he may have regretted his decision when the questions began to bore in on his personal finances and not the murder of Yale.

“What has money got to do with it?” the Big Fellow asked at one point. He’d known for months that the feds were looking at his taxes, but he may have been fooled because no representative of the Bureau of Internal Revenue had come to the meeting.

By the time the interview was done, news of the massacre in Chicago had spread by telephone and telegraph wire across the country. The black-and-white photos accompanying the stories were among the most graphically violent ever to appear in the American press. Chicago may have already been known as the nation’s gangland murder capital, but this crime was shocking even by Chicago standards.

Capone, still feeling cocky, would brag in the days after the crime that he had an airtight alibi: his Dade County sit-down with the law. But it didn’t matter. This crime raised the nation’s simmering resentment over gangland violence to a boil. From coast to coast, people seemed suddenly to reach the conclusion that a line had been crossed, that the violence had become too much, that the experiment known as Prohibition had blown up once and for all.

In Chicago, the mild-mannered U.S. attorney George E. Q. Johnson—the man in charge of the federal effort to put Capone behind bars—called the massacre “the most amazing crime in Chicago’s amazing criminal history.” Detectives, federal law-enforcement officers, and newspapermen blanketed the city’s North Side, talking to neighbors, searching for the killers’ black Cadillac, trying to make sense out of what had happened. Nobody knew.

Was this the work of Capone? Sure, he might have wanted to hurt Moran, given their competing interests in booze and gambling, the thinking went, but Moran also had plenty of other enemies around town. Besides, Moran wasn’t even in the garage at the time of the killing. There remained a strong possibility that the killing had nothing to do with him. Maybe the assassins were gunning for the Gusenbergs, who had an uncanny knack for getting in trouble. Or maybe the motive was something much simpler. Maybe it was business related. Almost every day in Chicago someone was hijacking a bootlegger’s truckload of booze or muscling a speakeasy owner to get him to switch suppliers. These disputes routinely ended in violence.

Every hour, more clues and more theories emerged among cops and newspaper reporters, until no one could possibly keep them straight.

Some investigators initially pursued the simplest and most obvious explanation: that Frank Gusenberg had been right in blaming the cops. After all, the men looked like cops, and their vehicle looked like a police car. The investigators quickly dispensed with that theory, though, claiming that Gusenberg must have been mistaken and that the men in uniform must have been impostors. They never explained their reasoning. Their next theory was that the murder had been the work of the Purple Gang, an outfit from Detroit, acting in retaliation for the recent hijacking of a truckload of whiskey. Members of the Purple Gang had supposedly rented a room across the street from the garage, presumably so they could watch for the arrival of Moran’s men. Then came the notion that the killing might have been connected to a vicious aldermanic election in the 20th Ward, where Capone supported one candidate and Moran another. Investigators also considered the possibility that the killing was tied to the fight for control of the dry-cleaning rackets. Albert Weinshank, one of the dead men, was a central figure in the laundry business.

Police even considered Moran himself as a suspect at one point. The gang boss was seen driving past the garage at about the time of the murder. Why didn’t he go in? Was it possible that he had tired of the Gusenbergs’ insubordination and decided to put an end to it? But why would Moran eliminate the other, innocent members of his gang, including a lowly mechanic?

After five days of hopping from one theory to another, police officials reverted to their original notion, saying they had new evidence suggesting that the killing had in fact been the work of police officers.

Moran’s gang had stolen a truckload of liquor from a crooked cop, according to a story in the Chicago Evening Post, and the unnamed cop had retaliated. The Evening Post quoted a witness who said that the car seen in front of the garage was “a police squad automobile beyond any doubt. It even had a gun rack fastened on the rear of the front seat.”

A week after the crime, cops found a stripped-down, burned-out Cadillac that may have been the one used in the St. Valentine’s Day attack. Still, the investigation went nowhere. “I can name 50 motives for this crime,” complained David Stansbury, the lead investigator for the state’s attorney’s office, “but no one stands out as being important enough to be called the probable cause of the murders.” The only thing Stansbury seemed fairly sure of was that Al Capone had not been involved.

The police had been looking for “Machine Gun” Jack McGurn, Capone’s top executioner, on the hunch that he was always a suspect when multiple shots were fired. But when they finally located him, Machine Gun Jack didn’t seem worried. “Me, mixed up in that gang killing?” he chortled. “Don’t make me laugh! The Gusenberg boys would have plugged me if they saw me a block away.” Asked by an Evening Post reporter for his own theory on who had killed Moran’s men, McGurn did not hesitate: “It was coppers,” he said flatly.

A decent answer, too, although not a perfectly satisfying one. For starters, it didn’t explain why the men had gathered in the garage that morning, why they were so well dressed, or why Bugs Moran was not among them. If the cops had indeed wanted to kill Moran’s men, why didn’t they do it in the usual way—by arresting them, shooting them, and claiming subsequently the men had tried to escape?

Also, it would appear that at least two of the dead—the mechanic, Johnny May, and the optometrist, Reinhardt H. Schwimmer—were innocent victims. For these men to get killed, the perpetrators must have been acting in anger, with little interest in precision. There must have been more than money involved. Finally, if the attack was made in retaliation for the theft of whiskey, why didn’t the killers empty the pockets of their victims and recapture at least some of their lost revenue? The dead men had thousands of dollars in their pockets. Not a dime was taken.

Less than one month after the crime, Herbert Hoover took the oath of office as the nation’s 31st president. Seven months before the stock market crash, America’s prospects still looked rosy. Yet, like a fussy schoolmarm, Hoover found it necessary to caution Americans that grave danger loomed. “The most malign of all these dangers today is disregard and disobedience of law,” he said. “Crime is increasing. Confidence in rigid and speedy justice is decreasing.”

Right away, he began asking about progress in the case against Capone. Hoover believed the arrest of the gangster would show Americans that his administration intended to enforce the law with vigor. What he learned, though, was that George E. Q. Johnson, the prosecutor heading the effort in Chicago, had so far failed to find any solid evidence to indict Capone. Johnson thought he might be able to bring a contempt of court charge based on a note Capone had submitted from his doctor claiming the gangster was too sick to appear in court. Johnson thought it was a lie. But the prosecutor also realized he would face ridicule if perjury was the best charge he could come up with.

On March 20th, Hoover met at the White House with a group of prominent Chicagoans. “They gave me chapter and verse for their statement that Chicago was in the hands of the gangsters,” the president recalled years later in his memoirs, “that the police and magistrates were completely under their control, that the governor of the state was futile, that the Federal government was the only force by which the city’s ability to govern itself could be restored.”

Given the pressure, and given the struggles of Johnson to put together a case, it begs the question: Why not charge Capone as an accessory to murder in the St. Valentine’s Day Massacre? Even if the evidence was weak, what harm was there in trying? At the very least, they’d get a chance to drag him into court and ask him questions.

But it never happened. Hoover and Johnson were both straight arrows. They had no evidence connecting the gangster to the killing, and they couldn’t bring themselves to play dirty—not even with Capone.

If before E.Q. Johnson was humiliated by his failure to bring charges against Capone, his shame only deepened a few months later when Capone was arrested in Philadelphia for carrying a gun and sentenced to a year in jail. The national press scoffed: Why hadn’t anyone in Chicago ever thought of that?

In December 1929, while Capone was on ice, police finally caught what looked like a big break in the St. Valentine’s Day Massacre case. On the evening of December 14, 1929, Fred “Killer” Burke, a well-known bank robber and hired gun, smashed his car into another near the police station in St. Joseph, Michigan, a hundred miles from Chicago. When a cop came after him, Burke shot him dead. Police searched for Burke at his home near the town of Stevensville. They didn’t find him, but they did discover a huge arsenal, including two machine guns, seven revolvers, eleven tear-gas canisters, and enough ammunition to support the overthrow of a small government. Ballistics tests provided dramatic results: Burke’s machine guns were the same ones used in the St. Valentine’s Day Massacre. And one of them had been used in the assassination of Frankie Yale in New York.

Astonishingly, though, Burke was never charged with either of those crimes. If Chicago authorities ever asked him whether the guns had been in his possession on February 14, 1929, or if he had been working for Capone at the time, his answers were never made public. After eluding the cops for more than a year, Burke was arrested on March 26, 1931, and sentenced to life in prison for the murder of the St. Joseph officer. In 1940, he suffered a fatal heart attack in prison. He was never pressed to answer questions about the St. Valentine’s Day Massacre.

On its face, it defies logic. How could a man in possession of weapons used in the massacre—a notorious gangster with ties to Capone—not be deemed a serious suspect? How could the Chicago police or the Department of Justice possibly explain the failure to consider charging him?

Only one answer makes sense: If the feds couldn’t pin it on Capone, they preferred to at least permit the cloud of guilt to hang over him.

Fast-forward four years, to January 1935. A bank robber named Byron Bolton, already in custody on an unrelated charge, is looking to reduce his time in jail and tells the feds he knows who committed the St. Valentine’s Day Massacre. He names Burke and four other men. Bolton says he was a lookout on the job. He says Capone ordered the hit in order to kill Bugs Moran.

Bolton’s story makes huge headlines across the country, even though it doesn’t entirely add up. At least one of the men he identified as a killer had an alibi. Then there is the question of why Capone would hire so many men for a job that required only one assassin. Capone knew where the rival gangster lived. He could have put Jack McGurn or another hired gun in a car across the street and had him wait until he got a clean shot. Sending in a hit squad was completely out of character for Capone and highly unlikely, given that the feds were following his every move at the time. But even if Capone had ordered the hit, and even if the job had gone horribly wrong, another question remained: Why hadn’t he ordered his men to try again? Why was Moran still alive?

And then there’s this: If Bolton’s story were true, why didn’t anyone use his testimony to bring charges against Capone? It wasn’t too late.

As it happened, nothing official came of Bolton’s so-called confession. But his highly publicized yarn did catch the eye of a Chicagoan named Frank T. Farrell. When Farrell read Bolton’s version of events, he sat down and composed a letter to John Edgar Hoover, head of the federal Bureau of Investigation—dated January 28, 1935—saying he had information that might be useful to the feds. His account—recently discovered in the FBI archives and never before revealed—offers the most logical and satisfying solution to the crime ever presented.

In cramped but tidy script, Farrell told the director that he had been doing “Undercover Investigation” work—he gives no more detail than that, and neither do the FBI archives—at the time of the crime. He said that if federal agents would check Chicago police logs, they would find that a 40-year-old former firefighter named William Davern Jr., the son of a Chicago police sergeant, had been shot during a bar fight in November 1928. Davern, the letter said, was the key to unraveling the mystery of the St. Valentine’s Day Massacre.

Davern had been in the kitchen of the C. and O. Restaurant at 509 North Clark Street, a popular gangster hangout, when a fight erupted. Davern was shot in the stomach. Spurting blood, he was carried to a car, driven to the corner of Rush Street and Austin Avenue (now Hubbard Street), and dumped there. Davern managed to crawl to a fire-station call box and ring for help. He was taken to the hospital, where he held on for a month. And while he wouldn’t tell the police who had shot him, Davern did tell his first cousin, William White. William Davern and William White had grown up together in Chicago. Now, as he lay dying, Davern decided there was only one man he could trust, and so he gave White the names of several members of the Moran gang, including one of the Gusenberg brothers. In his letter, Farrell doesn’t say which brother. Those are the guys who shot me, Davern told his cousin.

William “Three-Fingered Jack” White was beady-eyed, bald, and double-chinned. He was even tougher than he was ugly. A boyhood accident or a botched safecracking job—accounts varied—had taken two of the fingers on his right hand. For the better part of the decade he had maintained status as one of Chicago’s most vicious criminals, with a rap sheet as long and savage as the processing line at the Armour meatpacking plant. When Davern died, according to Farrell’s letter, White made up his mind to avenge his cousin’s murder. He contacted the same Gusenberg brother who had been involved in the murder of Davern and said he was planning to hold up a factory for its payroll and needed men to help.

White probably knew both the Gusenbergs. They had allegedly worked together in 1926 on the $80,000 robbery of the International Harvester factory on 31st Street. In that job, they had used eight men, and when one of those men ratted to the cops and started naming his accomplices, White arranged for two of his cohorts to disguise themselves as police, go to the rat’s home, and murder him while he slept. White knew that when people saw police uniforms they tended to be more trusting, and they tended not to notice the distinguishing features of the men in the uniforms. All they saw were hats and badges. And getting uniforms was easy. White knew plenty of crooked cops. In this case, he might have enlisted the help of his uncle, Sergeant William J. Davern, of the Chicago Police Department, the father of the man killed at the C. and O. Restaurant.

Farrell’s letter resolves many of the mysteries surrounding the massacre. It helps explain why so many of Moran’s men were in the garage that morning, why they were dressed well, and why they never fired their guns when faced by their intruders. It also offers a clear motive—one with enough emotional power to explain the fury of the attack. It may even account for why the investigation of the crime went nowhere. Perhaps word had spread through the police department that the garage killing had been carried out in retaliation for the murder of a cop’s kid. Sergeant Davern might have provided the uniforms and the police car. That could have been enough to quell further investigation and persuade the detectives to accept this rough justice.

If White had been arrested and confessed that he’d committed the crime in retaliation for the murder of Davern, the newspapermen certainly would have followed up with the next logical questions: Was Sergeant Davern involved? Did other cops help him commit or cover up the crime? And once those questions were asked, the reporters no doubt would have cited the dying words of Frank Gusenberg, which to this day remain the only testimony from a victim of the crime.

“Cops did it,” Gusenberg had said.

Shortly after the massacre on Clark Street, two eyewitnesses came forward to tell police that they had seen some of the action on the street. Their testimony seemed inconsequential at the time and was quickly forgotten, but it included this nugget of information from one of them: “Just about the time I arrived in front of the place, an automobile I thought was a police squad car stopped in front of the garage. There were five men in it. The fellow who stayed at the wheel had a finger missing. His hand was spread out on the steering apparatus, so the old amputation was apparent.” Police, it seems, never followed up on the lead.

For several years in the early 1930s, White worked as a federal informant, supplying information about Chicago hoodlums to federal agents in exchange for their protection, according to FBI documents released under the Freedom of Information Act. If John Edgar Hoover knew of White’s role in the St. Valentine’s Day Massacre, the bureau might have helped to cover his tracks for fear of losing an informant and jeopardizing the lives of the agents who worked with him.

In January 1934, when some of his peers figured out that White was a rat working for the Bureau of Investigation, White was executed in his home. Federal agents were seen visiting White at home shortly before the murder. The killers were never caught.

A year later, when Hoover received the letter from Frank T. Farrell suggesting that White had been responsible for the nation’s greatest unsolved crime, the director replied that the gangland killing was a matter for local police and of no interest to the bureau. In other words, as far as he was concerned, the case was closed. Farrell was never again heard from. Recent attempts to locate his family were unsuccessful.

Whether Capone had anything to do with the St. Valentine’s Day Massacre or not, one thing is clear: He was punished for it. The crime lit a fire under the federal prosecutors. Capone’s imprisonment became a national priority. The U.S. attorney eventually settled on a charge of felony income-tax evasion, and he wound up winning the stiffest sentence ever handed down for such a crime at the time: 11 years.

“A blow to the belt,” Capone called it. “But what can you expect when the whole community is prejudiced against you?”

The punishment proved effective: When Capone emerged from prison, his mind was wrecked by syphilis, and his criminal power was gone.

Over the course of his prison term, the great gangster was interviewed dozens of times by psychiatrists and prison officials. He spoke of his regrets: He said he wished that he had not been so friendly toward the press, because the publicity he earned had put a target on his back. He said he felt that his lawyers had failed him and that the judge assigned to his case had been unfair. He apologized for the grief he had caused his mother, his wife, and his son.

But he never spoke of the St. Valentine’s Day Massacre, the crime that helped cement his legend and end his career.

He never knew what hit him.

This article appears in the May 2010 issue of Chicago magazine. Subscribe to Chicago magazine.

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