HAPPY ST. PATRICK’S DAY… WITH A BULLET

THE RISE & FALL OF DEAN O’BANION

One of America’s most successful Irish gangsters was Dean O’Banion, who ran the liquor operations on the North Side of Chicago during the early days of Prohibition. At the start of Prohibition, when John Torrio divided up the territories among the opposing factions, O’Banion managed an area between the Chicago River and Lake Michigan. It was a lucrative area that was given to O’Banion to keep him in line. He was, undoubtedly, Torrio and his protégé Al Capone’s most dangerous opposition. He was an often reckless Irishman who always carried three guns with him. He could shoot accurately with either hand. Chief of Police Morgan Collins once called him “Chicago’s arch criminal” and stated that O’Banion “has killed or seen to the killing of at least twenty-five men.”

Chicago Irish gangster Dean O'Banion

O’Banion never spent a day in jail for shooting any of those men. His political usefulness was too great. O’Banion controlled the Irish vote in the city and while bribery and intimidation usually did the trick, he and his men never hesitated to beat, kidnap and murder. He always delivered his district and the Democratic bosses of the Forty-Second and Forty-Third wards prized O’Banion’s vote-getting abilities so much that they once gave him a testimonial dinner at the Webster Hotel and presented him with a gem-encrusted platinum watch. Among those present at the dinner were Colonel Albert Sprague, the Cook County commissioner of Public Works and a Democratic candidate for U.S. Senate; Robert M. Sweitzer, then Cook County Clerk; and Chief of Police Michael Hughes. Ironically, O’Banion personally always voted Republican.

Schofield's Flower Shop, in which O'Banion had a controlling interest. He used the upper floor as the headquarters for his rackets. 

To offset his violent involvement in the rackets, O’Banion loved flowers. He acquired a half interest in William Schofield’s flower shop at 738 North State Street, directly across the street from Holy Name Cathedral, where he once served as an altar boy. On most days, he could be found in the shop, cutting flowers, potting plants and putting together arrangements for weddings and burials. He became gangland’s favorite florist, which was a lucrative business because underworld etiquette required both friends and foes of a fallen gangster – including the man who killed him – to honor him with elaborate floral creations. Everyone ordered from O’Banion and the moment that word reached him of a gangster’s demise, he was on the telephone to his wholesale supplier. At the same time the undertaker was starting to prepare the corpse, and before the orders even started coming in for flowers, O’Banion and his staff were already at work making wreaths and elaborate bouquets and choosing banners that could be gilded with suitable sentiments like “Sympathy from the Boys” and “Gone, but not Forgotten”. All a caller had to do was telephone the shop, identify himself and name the amount he wanted to spend. O’Banion would take care of the rest.

O’Banion was happily married and his wife, Viola, insisted that he was a devoted family man: “Dean loved his home and spent most of his evenings in it. He loved to sit in his slippers, fooling with the radio, singing a song, listening to the player piano. He never drank. He was not a man to run around nights with women. I was his only sweetheart. We went out often to dinner or the theater, usually with friends. He never left home without telling me where he was going and kissing me goodbye,” she told an interviewer.

O'Banion and his loving wife, Viola

Dean and Viola never had children. They occupied a twelve-room apartment on North Pine Grove Avenue. He drove a late-model Locomobile and his proudest possessions were a player piano, for which he had paid $15,000, and a Victrola. He was constantly setting them up to play the same tune and trying to synchronize them. Sadly, he died before the invention of stereophonic sound systems, for a set of speakers would have produced the effect that he sought. He dressed stylishly, always wearing a tuxedo when he attended the theater or went out to dinner. He spoke well, minding his grammar, and insisted that his associates follow proper etiquette. O’Banion walked with a limp, his left leg being shorter than his right, the result of a boyhood fall from a streetcar, but he was otherwise unremarkable. He was strong and fit with a round face, cleft chin and a genial personality. 

Dean (he later adopted the name Dion) Charles O'Banion had been born in 1892 in the small Central Illinois town of Maroa. His father, Charles, was a barber by trade who hailed from Lincoln, Illinois, and his mother, the former Emma Brophy, was the Chicago-born daughter of an Irish immigrant father and American mother. She had been just eight months old when the Great Chicago Fire leveled the city in 1871. Charles and Emma married in 1886 and moved to Maroa the following year, where Charles' parents lived.

Dean spent the early years of his life in Maroa but soon after the birth of his sister, Ruth, his mother contracted tuberculosis and died in 1901. Dean was only nine years old at the time and the loss was a devastating one. The remaining family members packed up and moved to Chicago, where Emma's parents had a place for them. With the move came the end of Dean’s innocent years. The hard times, and the legend, were about to begin.

Upon moving to Chicago, O'Banion found himself turning to the streets for a playground. The family settled in a tenement flat on the edge of the North Side’s Little Sicily, a maze of narrow, dirty streets that reeked of smoke from the nearby factories. The flames from a gasworks chimney that reddened the sky at night gave the neighborhood its nickname – Little Hell. It had formerly been an Irish neighborhood dubbed Kilgubbin and about a 1,000 Irish remained. The Sicilians started arriving around 1900 and were soon the majority. Although only a square mile in size, Little Hell was one of the most dangerous spots in the city and averaged between 12 and 20 murders each year.

O’Banion became involved with a junior street gang known as the Little Hellions and began picking pockets and rolling drunks. At the same time, he sang in the choir at the Holy Name Cathedral and, on Sundays, he served as an altar boy. Some of the priests at the church believed that perhaps his devotion might lead to a calling to the priesthood but O'Banion soon learned to ration his religion to Sundays and to devote his remaining time to robbery and, as he reached young adulthood, to burglary, what he called "a man's profession." He soon hooked up with a number of other hardcase young men, including George “Bugs” Moran, Earl “Hymie” Weiss, Vincent “The Schemer” Drucci and Samuel “Nails” Morton. With these toughs at his side, O’Banion put together one of the most devastating gangs in Chicago history. They devoted themselves to burglary, safecracking, and after 1920, to bootlegging.

In 1909, O’Banion served three months in the House of Correction for robbery and two years later, another six months for beating a victim. Those short sentences turned out to constitute his entire prison record. He soon demonstrated his ability to bring in votes and he was able to count on his political patrons to keep him out of jail.

A handful of missteps were all that ever gained the attention of the police. He was not always the most subtle of safecrackers. Once, when attempting to open a safe with a stick of dynamite, he blew out the entire side of an office building but barely put a scratch on the safe. In 1921, Detective Sergeant John J. Ryan caught O’Banion, Hymie Weiss and a couple of other men in the act of blasting open a Postal Telegraph safe. O’Banion cheerfully told the police officer things weren’t as they appeared – they were actually in the office late that night applying for jobs as apprentice telegraph operators. An alderman furnished a $10,000 bond for O’Banion and another $30,000 in bribes to make the case go away. Not long after, the fingerprints of O’Banion, Weiss, and Vincent “The Schemer” Drucci, were found on the dial of an empty safe in the Parkway Tea Room. A jury acquitted them. O’Banion spoke to a reporter when he left the courtroom: “It was an oversight. Hymie was supposed to wipe off the prints but he forgot.”

O’Banion might have had a questionable reputation with the authorities, but was well liked in the neighborhood. As his fortunes soared, his acts of charity went beyond those of a man just trying to make himself look good. He had genuine feelings for poor and miserable people such as his parents had been. Often, the police would get excited when they saw O’Banion’s car cruising about in the shabby districts and suspected that a crime was in the wind. In truth, he was merely out on an expedition of charity, his car filled with food and clothing. He visited the slums, dropping off money for widows, the elderly and the orphans. He gave groceries to those who couldn’t afford them, bought shoes for ragged children and kept many men and women from the poorhouse. A newsboy would sometimes be stunned to find that O’Banion gave him $100 for a two-cent paper. He sent many sick children to the hospital and paid their medical bills. He once sent a crippled boy to the Mayo Clinic and, when told that neither surgery nor medication could cure him, set up a trust to take care of him for as long as he lived.

O’Banion also had an odd sense of justice. After an altercation at the LaSalle Theater that put a man named Dave Miller in the hospital for several weeks -- O’Banion later apologized, saying, “it was just a piece of hot-headed foolishness,” -- Miller’s brother, Hirschie, was approached by someone who offered to kill O’Banion for money. The would-be assassin’s name was John Duffy and he came to Chicago after killing a policeman in Philadelphia. He was a blustering, swaggering fellow who was proud of the fact that he had committed four murders. He had earlier met O’Banion and the Millers (who were usually friends – the Millers declined to prosecute Dean for the shooting) and all of them sized Duffy up as a drunken braggart and wanted nothing to do with him. Duffy approached Hirschie about killing O’Banion and Hirschie turned him down cold. He later told O’Banion about it and while angry, he vowed to watch his back around the man. He and the Millers were convinced that Duffy was crazy and Hirschie warned him, “Lay off that guy. He’ll kill somebody yet.”

Duffy continued to throw his weight around in Chicago with no thought of danger. He was oblivious to the fact that his situation was growing precarious. He brought it to an abrupt climax with an impulsive but brutal crime that offered O’Banion the perfect excuse to revenge himself on Duffy.

At the time Duffy was living with a likable young woman named Maybelle Exley in a little apartment on Carmen Avenue on the North Side. They had a volatile relationship, mostly caused by Duffy, who sometimes flew into terrible rages when he was drinking. One night, a pal named Billy Engelke was drinking with them in their apartment and Duffy went into another of his alcohol-fueled outbursts. Suddenly, he pulled out a revolver and shot Maybelle in the head. She was dead before she hit the floor.

Duffy snapped. He began to weep as though his heart was broken and began rushing up and down the room, waving his arms and crying. He couldn’t believe what he had done. Billy Engelke later said that he was sure the man had gone insane. Duffy picked up Maybelle and gently laid her down on the davenport. He bent down and kissed her on the forehead before covering her with a sheet. “Goodbye Maybelle,” he said.

Panic-stricken, Duffy knew that he had to get out of Chicago. Not knowing what else to do, he went to see O’Banion. He told O’Banion that he had “accidentally” killed his sweetheart and needed money to leave town. O’Banion listened in silence and then told him that he would meet him later that night. O’Banion drove up alone to where Duffy and Engelke waited for him, arriving around midnight. He had a few words with Duffy, told him that he had a plan for him to escape, would stake him some money and drive him to an outlying railway station where he could board a train without worrying about the police finding out. Duffy, feeling better with the prospect of a safe getaway, climbed into the car with O’Banion and they drove off into the night.

Duffy was found dead the next morning with three bullet holes in his head. O’Banion had his revenge – and he managed to get a little justice for the poor farm girl who had died at Duffy’s hand.

On another occasion, one of O’Banion’s close friends, Samuel “Nails” Morton (who earned his famous nickname for being “tough as nails” fighting in the streets of the old Maxwell Street neighborhood) was killed by an unlikely adversary. Morton and O’Banion were avid horseback riders and the men liked to rent horses from the Brown Riding Stables at 3008 North Clark (later the site of the old Ivanhoe Theater) and then go riding in Lincoln Park.

On this morning, Morton mounted a frisky colt named “Morvich” after a famous jockey of the day. The plan was for “Nails” to ride east down Wellington toward the Lincoln Park bridle path, where he would rendezvous with friends. Unfortunately, the nervous horse began behaving erratically and as Morton rode away from the stable, Morvich bolted south down Clark Street. Near the intersection of Clark and Diversey, Police Officer John Keyes saw how fast the animal was approaching and tried to curb him when he realized the rider has lost control. Then suddenly, the left stirrup gave away and fell to the ground. Morton clung to the horse’s neck, and then decided to take a chance and jump to the ground. He landed headfirst on the street and on the way down, one of the horse’s hooves hit him in the head, causing a skull fracture that would turn out to be fatal. Morton was rushed to the hospital and died on the operating table.

As far as his pals were concerned, “Nails” had been murdered – a crime that could not go unpunished. Late on the night of his funeral, several members of the North Side gang broke into the Brown Riding Stables and executed the guilty horse. One of them later telephoned the stable manager and told him “we taught that horse of yours a lesson.” Dean O’Banion threw a party in celebration of this unusual act of vengeance.

Chicago crime boss John Torrio

For three years after Torrio divided Chicago into gang territories, O’Banion remained in the good graces of Torrio and Capone. In fact, after the death of Frank Capone in April 1924, he had even prospered because of that uneasy friendship. Capone had not forgotten the extravagance with which O’Banion had prepared the arrangements for his brother’s funeral and he maintained a grudging fondness for the North Side gangster that likely kept the man alive longer than he deserved to be. O’Banion’s business flourished, not just the flower shop, but bootlegging, which was netting him almost a million dollars a year. He supplemented his income with daring hijackings that netted him high-quality whiskey, pulled off trucks by members of his eccentric gang. On one occasion, he raided a warehouse that contained almost 2,000 barrels of liquor and replaced the booze with water as a joke. In spite of all this, he wasn’t happy. Officially, he was allied with Torrio and Capone, which offered him protection from rival bootleggers and the numerous freelancers that lurked about Chicago, but even though he had contributed men to act as muscle during the Cicero election, he felt slighted, used and unappreciated.

To improve O’Banion’s mood, Torrio offered him a small piece of the action in Cicero, a beer territory that added up to less than $20,000 a month – walking-around money by the standards of the Torrio organization, but it was still something. O’Banion took it and ran with it. He owed his talent for making money to the fact that he was a little bit crazy and he proved this once again by encouraging speakeasies to move to Cicero. Torrio and Capone were impressed and more than a little resentful. Capone complained about giving O’Banion the territory to begin with and urged Torrio to take it back. But ever the peacemaker, Torrio proposed that O’Banion kick back a percentage of his new business in exchange for a percentage of the outfit’s income from prostitution. The deal was typically Torrio, linking possible adversaries in a mutually beneficial enterprise. But O’Banion, like many Irish-Catholic racketeers, hated prostitution. It was a filthy business they believed better left to the Italians and the Jews. During his time as leader of the North Side, not a single bordello could be found in Chicago’s Gold Coast neighborhood. He refused Torrio’s deal.

O’Banion tolerated Torrio and Capone but he outright despised their closest allies, the “Terrible Gennas.” The Gennas sold their homemade poison for just $3 a barrel, which was half the price of O’Banion’s high-class whiskey. Each of their stills produced as much as 350 gallons of the wretched high-proof stuff each week with ingredients that cost less than $1 a gallon. When the Gennas began selling their whiskey in O’Banion’s territory on the North Side, he implored Torrio to send the Sicilians back to their own neighborhood on the West Side. Torrio stalled for time. He knew how dangerous the Gennas were – heavily armed, entrenched in Sicilian blood oaths and connected to the police – and he didn’t want to get involved in the dispute. So, O’Banion dared to do what no sane bootlegger would do and hijacked a truck that carried $30,000 of the Gennas’ liquor. The Sicilians were infuriated but with Torrio acting as a peacekeeper, the animosity between O’Banion and the Gennas stopped short of bloodshed.

Even though the situation was close to boiling over, O’Banion made matters even worse by developing his own private relationship with the police. Capone complained, “He was spoiling it for everybody. Where we had been playing a copper a couple of hundred dollars, he’s slip them a thousand. He spoiled them.” In return for his money, O’Banion received information that he planned to use against his bootlegging partners in a complicated scheme that proved just how clever – and reckless – he could be.

Six weeks after the funeral of Frank Capone, and days after the murder of Joe Howard, O’Banion paid a visit to the Hawthorne Inn in Cicero. He met with Torrio and Capone and stunned them with the news that he planned to retire from bootlegging. He was tired of dealing with the Gennas, he explained, and wanted to leave the dangerous life in Chicago and settle down in Colorado. Although they tried not to show it, Torrio and Capone were thrilled by the news and were even happier when O’Banion named his price. The three men jointly owned the Sieben Brewery and O’Banion offered to sell his share for half a million dollars. He even volunteered to transport the last shipment of beer as partners; it was scheduled to go out on May 19, 1924. Torrio and Capone immediately agreed to his terms and saw to it that O’Banion received his payment in full.

Sieben Brewery -- years after O'Banion sold out to Torrio

Unknown to Torrio and Capone, O’Banion’s offer to sell his share of the Sieben Brewery was nothing more than an elaborate ruse. Prior to the meeting, he had learned through his police contacts that the brewery was going to be raided by the police on the night of May 19. Normally, a brewery raid was of little concern in Chicago. It usually just meant that a precinct captain had not been paid off, or wanted more money, and it was easy to avoid if the right amount of cash ended up in the right pocket. But this raid was different. This time, federal authorities under orders from the U.S. Attorney were running the operation with Mayor Dever’s full approval. Since Torrio already had a prior federal conviction for violating Prohibition laws in 1923, a second conviction would lead to a large fine and a mandatory jail sentence.

On the night of May 19, the raid on the brewery occurred just as O’Banion knew it would. Torrio and O’Banion were supervising the loading of the trucks that would take the beer to speakeasies all over Chicago when the police broke in and arrested everyone in the place. Torrio was detained, as was O’Banion, so that he could maintain the ruse that he knew nothing about the raid. Only Capone managed to avoid arrest since he was not present at the brewery that night. Once Torrio was delivered to the federal authorities, he realized that O’Banion had betrayed and humiliated him. Seething, he refused to post bond for O’Banion, as he routinely did for his other partners and employees. Torrio himself was soon free on bail, but he was later convicted of owning a brewery and was sentenced to nine months in jail and a $5,000 fine – all thanks to Dion O’Banion.

After the raid and Torrio’s arrest, O’Banion’s days were numbered. Strangely, he seemed completely oblivious to the fact. He worked each day at his flower shop, cheerfully greeting his customers and spent his evenings at home or having dinner with his friends. Months passed and O’Banion had no idea that several of his old bootlegging partners were plotting his demise. Only Torrio hesitated to have him killed. He knew that O’Banion’s death would spark all-out war in Chicago. However, after the brewery raid, even the cautious Torrio was leaning toward O’Banion’s murder.

On November 3, O’Banion and Hymie Weiss arrived at The Ship, a Capone-run gambling joint in Cicero, to divide up profits with his partners. Business proceeded as usual until Capone mentioned that Angelo Genna had racked up $30,000 in gambling debts that had never been paid. In the interest of preserving the peace, Capone suggested that they forgive the debt. O’Banion adamantly refused. He went straight to a telephone, called Genna, and demanded that he pay the debt within a week’s time. Capone and Torrio were shocked at O’Banion’s rash behavior. Capone and Torrio were doing all they could to keep the murderous Gennas happy, but they could not control the reckless O’Banion – and were not sure they really wanted to. As they left the gambling den that day, Weiss cautioned O’Banion to stop antagonizing the Gennas and Torrio. But O’Banion, in a typically rebellious mood, waved away his friend’s words. “Oh, to hell with them Sicilians,” he said.

    

This bold statement soon became a refrain among O’Banion’s men and among many other Chicago bootleggers, most of whom felt the same way but had never been brave enough to say it out loud – to hell with the Sicilians. To the Gennas and other Italian mobsters, though, such words were the worst kind of insult and together with Torrio and Capone, the Gennas put the final touches on their plan to assassinate O’Banion. The murder would be carried out the old-fashioned way, which meant O’Banion would be killed face-to-face, at his place of business, in the middle of the day, and everyone in Chicago would know who was responsible and why it had been done.

To carry out such a public assassination, the Torrio-Capone organization required the blessing of Mike Merlo, the president of the powerful Unione Siciliane. Merlo was opposed to the idea of eliminating O’Banion, however. The murder was bad for business, he told them, and as long as he was in office, O’Banion would not be killed. Torrio took the news calmly for he knew that Merlo was suffering from end stage cancer and would not be around to protect O’Banion for long. He would be patient, knowing the time for action would come. He didn’t have long to wait – Merlo died on November 8.

Initially, Merlo’s death was a windfall for O’Banion, who promptly sold over $100,000 in flower arrangements to the mourners, including a spectacular floral effigy of the deceased that stood twelve feet high. Capone himself purchased $8,000 worth of flowers. O’Banion also received unusual order, so small that he almost overlooked it. Jim Genna, one of his sworn enemies, visited the store and ordered a wreath for Merlo’s funeral. He gave O'Banion $750 to pay for the arrangement and told him that some boys would be by   to pick it up on Monday morning. He left the shop quietly, barely speaking, but he was there long enough to put together a mental blueprint of the place – just in case he had need to visit it again.

The selection of Mike Merlo’s successor as president of the Unione Siciliane brought Frankie Yale back to Chicago. As the head of the powerful New York branch of the organization, Yale had considerable influence over who took over the corresponding post in Chicago. He conferred with Torrio and Capone and the three men decided to appoint Angelo Genna to the position. As the new president of the Unione Siciliane – and a man who had been recently humiliated over a gambling debt by O’Banion and wanted to see him dead – he had no objection to the immediate elimination of the North Side bootlegger. This finally put into motion the most highly publicized and significant gangland slaying in Prohibition-era Chicago – the murder that would make Chicago a city at war.

On Monday, November 10, 1924, two days after the death of Mike Merlo, O’Banion left his apartment and went straight to Schofield’s flower shop on North State Street. There was still much to do in preparation for Merlo’s funeral and he spent most of the morning working on large orders for the event. He worked alongside three of his employees, surrounded by plants and flowers of every description. Late in the morning, the telephone rang and the caller asked if O’Banion had the Genna wreath ready to be picked up. O’Banion replied that it could be picked up at noon.

At five minutes past the hour, a blue Jewett sedan parked in front of the flower shop. The driver remained at the wheel, the motor idling, and the passenger door standing open. Gregory Summers, an 11-year old junior traffic officer who was guiding some children across the street near Holy Name Cathedral, saw three men get out of the car. “Two of them were dark and looked like foreigners. The other man had a light complexion,” he later said. The three men passed him and entered the flower shop.

Inside Schofield's flower shop -- where O'Banion met his end

O’Banion was in the back, working on a flower arrangement, but the porter, an African-American man named William Crutchfield, was sweeping up flower petals and looked up to see the men enter the shop. He assumed they were racketeers, like many of the men that O’Banion did business with. He didn’t recognize the men, but it was obvious that his boss did, which is likely why O’Banion never drew any of the three guns that he habitually kept hidden on his body. O’Banion, who was dressed in a long white smock and holding a pair of florist's shears in his left hand, came out from behind the counter and extended his right hand in greeting. He said to them, “Hello, boys. You want Merlo’s flowers?”

The three men walked abreast and approached O'Banion with smiles on their faces. The man in the center – either Frankie Yale or Mike Genna, depending on which version of the events you believe – reached out his own hand. The two men beside him were almost definitely John Scalise and Albert Anselmi. They were shorter and stockier, with dark complexions, and would kill anyone on the orders of whoever their boss happened to be at the time. 

Crutchfield heard the man in the middle reply, “Yes, for Merlo’s flowers.” He then stepped closer to O’Banion, grabbed his hand in greeting and pulled him close. The two men at his sides moved around him and drew pistols. Then, at close range, the center man rammed his own pistol into O'Banion's stomach and, holding his arm in a vice-like grip, opened fire. The other two men also fired their weapons, the bullets ripping into O'Banion. Two slugs struck him in the right side of the chest, two hit him in the throat and one passed through each side of his face. The shots were fired at such close range that powder burns were found around each wound. From that point on, this up close and personal method of murder became known as the "Chicago Handshake."

The leader of the North Side gang fell, having died on his feet, into a display of geraniums. O’Banion’s pistols were unfired, not even drawn. The three men fled from the store, jumped into the blue sedan and, as young traffic patrol Gregory Summers watched in amazement, sped away.

With the death of O’Banion, the Torrio-Capone syndicate had eliminated the most unpredictable and dangerous bootlegger in the city. They had also ingratiated themselves with the Gennas and set the wheels in motion to take over O’Banion’s wealthy North Side territory.  O’Banion’s funeral, for the South Side outfit, was not an occasion for mourning, but a time for celebration. Torrio and Capone were glad to see him go and were happy to contribute to his send-off. But it wouldn’t be easy. The Catholic Church, under the authority of Cardinal Mundelein, refused to permit a funeral mass for O’Banion to be held at Holy Name, the cathedral across the street from the flower shop and the place where the young O’Banion had served as an altar boy. Mundelein also forbade him to be buried in consecrated ground. But Torrio and Capone refused to let this dampen the festivities. They were intent on throwing O’Banion the most lavish gangster funeral that Chicago had ever seen.

The funeral procession was so large that it became the subject of national fascination. It extended for a mile and included three bands and a police escort dispatched by Capone from the village of Stickney. Chief Collins had issued an order that prevented Chicago police from joining the parade or an embarrassingly large contingent of city police officers would have most assuredly been involved. More than two dozen cars were required to transport floral tributes from the funeral home to the cemetery, including a large basket of roses that bore the ironic message: “From Al.”

For blocks in every direction, from the street, from the windows of office buildings, and from rooftops, thousands watched the cortege forming. It reached gigantic proportions – 10,000 people walked behind the hearse and when they reached Mount Carmel Cemetery, they joined another 10,000 mourners assembled at the gravesite. Mounted police had to clear a path through the mob so that the motorcade could advance. Every trolley car to the area near Mount Carmel was packed with curiosity-seekers.

A grave was dug for O’Banion in a section of unconsecrated ground. This area, reserved for lapsed or excommunicated Catholics, was as close to holy ground as could be found. At the grave, Father Patrick Malloy, who had known and liked O’Banion since he was a boy, delivered a short eulogy. Cardinal Mundelein had forbidden a funeral service, but Malloy defied him just enough to at least offer words of comfort and prayers. Five months later, Viola O’Banion managed to have her husband’s remains disinterred and reburied in consecrated ground. Although this was brought to the attention of Cardinal Mundelein, he did not have the body removed. A stone obelisk bearing O’Banion’s name stands in the cemetery today, a short distance from some of his rival gangsters and a few feet from a mausoleum that contains the remains of a bishop and two archbishops. The irony of this turn of events led Police Captain John Stege to remark, “Strange, isn’t it? A murderer and he’s buried side by side with good men of the church.”

The author at O'Banion's grave

Capone and Torrio were in attendance at the cemetery, although they knew that O’Banion’s friends saw past the elaborate floral arrangements and empty words of grief and knew exactly who was responsible for his death. A reporter came up to Hymie Weiss and asked him who he thought was responsible for O’Banion’s murder. Was it Al Capone? Weiss mockingly recoiled. “Blame Capone?” he asked, his voice dripping with sarcasm, “Why Al’s a real pal. He was Dion’s best friend, too.” Passions ran so high that all mourners were ordered to check their weapons until the funeral was over. It was likely a good thing. Capone and Torrio spent a long, uncomfortable afternoon being glared at across O’Banion’s grave by Weiss, Drucci and Moran.

Relieved that another racketeer was out of the way, the police didn’t try too hard to catch O’Banion’s killers. The half-hearted investigation went nowhere. As a matter of routine, they questioned John Torrio, Al Capone and the Gennas, all of whom claimed to revere O’Banion. They were deeply grieved by his death, they said, and pointed to the large and expensive floral arrangements they purchased as proof. Frankie Yale was also questioned but he claimed to be in town only to attend the funeral of Mike Merlo. He had nothing to do with the death of O’Banion, he said. After making a statement to the police, he returned by train to New York.

After the inquest, the Cook County Coroner made a note in the margin of the court record: “Slayers not apprehended. John Scalise, Albert Anselmi and Frank Yale suspected, but never brought to trial.” Officially, the murder of Dion O’Banion was marked with one word – unsolved.

O’Banion’s men had no doubts about who had carried out the assassination, though. They knew that Torrio, Capone and the Gennas were behind it and as Hymie Weiss assumed the leadership of the North Side gang, he swore out an oath of vengeance that started the city’s legendary “Beer Wars.”

The streets of Chicago were about to run red with blood.

Who Killed Jake Lingle?

WHO REALLY KILLED JAKE LINGLE?

The Reporter, the Tribune and the Mob

On this date, April 2, 1931, a small-time thug named Leo Brothers was sentenced to spend 14 years in prison for one of the most spectacular murders in Chicago gangland history. In this case, it was not an infamous mobster that was gunned down but an ordinary reporter for the Chicago Tribune named Jack Lingle. But was he really an ordinary reporter? In the wake of his death, most didn’t think so...

For Chicagoans who lived through the turbulent days of the “Beer Wars” in the city, crime, murder and violence became commonplace, but on Monday, June 9, a new and apparently different incident became the talk of the town. It was an outrage that was splashed across the front page of every newspaper in the city. This was the murder of Alfred L. “Jake” Lingle, a crime reporter for the Chicago Tribune, who was shot to death while walking, smoking a cigar, and reading the racing news in the crowded underpass at Randolph Street and Michigan Boulevard during the lunch hour.

$65-a week newsman for the Chicago Tribune Jake Lingle, who owned two homes, kept a fancy hotel suite, had a chauffeur-driven car and maintained a luxurious lifestyle. He was also a close friend of Al Capone. 

It would become the most sensational murder of 1930, even though prior to his death, the general public had no idea who Lingle was. In spite of this, his murder created a furor. In those days, newspaper reporters were not well paid, but they had a place in public regard that was generated by glamour, respect and authority. The murder of Lingle immediately assumed the importance of that of a public official – and was publicized by every newspaper in town.

Lingle’s duties on the police beat for the Tribune earned him $65 a week, which was not a princely sum. He had no aptitude for writing and could only transmit the facts. For eighteen years he had been a “leg man” who gathered crime news and phoned it in to the to the city editor’s desk. For writers at the Tribune, he was a great asset. Crime was front page news in the Chicago of the 1920s and every paper relied heavily on its in-house crime expert. In that category, Lingle had no equal. He frequently scooped the competition, for not only did he enjoy easy access to Capone, he was on intimate terms with both Police Commissioner Russell and Deputy Commissioner Stege.

Lingle never had a by-line in the paper and his name was unknown to most readers. To the public, he became much more famous in death than he ever was in life. And soon, he became notorious as details about his lifestyle began to be revealed. The supposedly humble reporter owned a chauffeur-driven Lincoln limousine and had just bought a $16,000 house at Long Beach on Lake Michigan, where his wife and two children were planning to spend the summer months. He also owned a house on the West Side but had recently taken a suite at the Stevens, one of Chicago’s most stylish hotels. He was an avid gambler at the horse and greyhound tracks, but his lavish way of life couldn’t be bought with winnings at the track.

On the day of his death, Lingle was on his way to the races. He had left his wife packing for her departure to the lake house and he planned to spend the afternoon at Washington Park in Homewood. Later that night, he planned to go to the Sheridan Wave Tournament Club, a society gambling parlor on Waveland Avenue, where the champagne, whisky and food were distributed with the management’s compliments during play. It was due to re-open that evening and Lingle wanted to be there.

In retrospect, it seems that Lingle knew he was in trouble. Attorney Louis B. Piquett later volunteered to the police that 24 hours before Lingle’s death, he had met with the reporter in the Loop. They stood on Randolph Street talking about the discovery of a murder victim named Red McLaughlin, whose body had been found in the canal. Lingle was giving Piquett his theory about the crime when a blue sedan with two men in it pulled alongside them and stopped at the curb. Lingle stopped talking in mid-sentence and looked at the men in a startled way. The two men simply stared at him. Lingle never finished what he was saying to Piquett. He simply told the attorney goodbye and walked into a nearby store. Also, on the day of his murder, after lunching at the Sherman Hotel he met Sergeant Thomas Alcock of the detective bureau and told him that he was being tailed.

And apparently, he was. After buying cigars at the Sherman Hotel kiosk, he walked the four blocks to Michigan Avenue to catch the 1:30 p.m. train to the Washington Park racetrack. He descended into the underground walkway that led to the Illinois Central suburban electric railroad in Grant Park. At that time of day, the subway was very crowded, filled with a steady stream of shoppers and office workers.

Oddly, though, even though he knew he was being followed, Lingle acted unconcerned. According to witnesses, he arrived at the entrance to the subway walking between two men. One had blonde hair and wore a straw boater hat and a gray suit. The other was dark-haired and wore a blue suit. At the entrance, Lingle paused and bought a racing edition of the evening newspaper. As he did so, a man in a roadster on the south side of Randolph Street blew his horn to attract Lingle’s attention. There were two men in the automobile and one of them called out, “Play Hy Schneider in the third!” According to a Yellow Cab superintendent who heard the exchange, Lingle grinned, waved at the man and called back, “I’ve got him!”

Lingle walked on into the subway, where he was seen by Dr. Joseph Springer, a former coroner’s physician and a long-time acquaintance. Springer later reported, “Lingle didn’t see me. He was reading the race information. He was holding it before him with both hands and smoking a cigar.”

Lingle had almost reached the end of the subway. He stopped across from the newsstand about 25 feet short of the east exit and the dark man who had been walking next to him moved away as if to buy a paper. As he did, the blonde man stepped behind Lingle, pulled out a snub-nosed .38 colt, and fired a single shot into the back of Lingle’s head. The single bullet drove upward into his brain and exited his forehead. Lingle pitched forward, cigar still clenched in his teeth and newspaper still in his hands.

The blonde killer tossed away the gun and ran forward into the crowds. Then, for some reason, he doubled back past Lingle’s body and ran up the eastern staircase. He jumped a fence, changed his mind again, ran west on Randolph Street, through a passage (where he tossed away a left-hand silk glove, probably used to prevent leaving fingerprints) and, pursued by a policeman, ran onto Wabash Avenue, where he disappeared into the crowd.

Death calls for Jake Lingle

Meanwhile in the subway, a bystander named Patrick Campbell saw the dark-haired man who had been walking with Lingle and the killer hurrying towards the west exit. He moved to try and catch him, but his movement was blocked by a priest, who bumped into him. The priest delayed Campbell just long enough for the accomplice to escape. He told Campbell that he was getting out of the subway because someone had been shot. Later, Lieutenant William Cusack of the detective bureau commented gruffly, “He was no priest. A priest would never do that. He would have gone to the side of the stricken person.”

Slowly, the method of Lingle’s murder became clear. He had walked into a trap that had been formed by perhaps as many as a dozen men. But what was never put forward as a theory, and which seems the most likely explanation, was that during his progress into the subway between the two men, he was eased along at gunpoint, under orders to keep walking naturally and keep reading the paper.

That evening, Colonel Robert R. McCormick, publisher of the Chicago Tribune, summoned his news staff together and addressed them about the death of a reporter that he had never met and whose name he had likely never heard before. He spoke for 45 minutes and pledged to solve the murder of the martyred journalist. The next morning, the front page of the paper blared with an eight-inch banner headline that announced the dead of Lingle. The story read: “Alfred L. Lingle, better known in the world of newspaper work as Jake Lingle, and for the last eighteen years a reporter on the Tribune, was shot to death yesterday in the Illinois Central subway at the east side of Michigan Avenue, at Randolph Street.

The Tribune offered $25,000 as a reward for information which will lead to the conviction of the slayer or slayers. An additional reward of $5,000 was announced by the Chicago Evening Post, making a total of $30,000.” The next morning, not to be outdone by the Tribune, Hearst’s Chicago Herald & Examiner also offered up a $25,000 reward, bringing the total up to $55,000.

Colonel McCormick, meanwhile, continued to take Lingle’s death as an affront to him personally and an attack on the press. He regarded it as being much more serious than the other hundreds of cases of violence that plagued Chicago. He announced that Lingle’s murder was committed in reprisal and as an attempt to intimidate the newspapers into suppressing stories about the dealings of the underworld. But, he declared, this was now a war and the Tribune and Chicago’s other newspapers would not rest until Lingle’s killers had been brought to justice.

What was especially shocking was that up to that point, gangsters had taken a “hands-off” policy toward harming reporters. Lingle was hailed as a hero who died in the service of the public and over 25,000 people attended his funeral.

Police Commissioner Russell was forced into making a statement. “I have given orders to the five deputy police commissioners to make this town so quiet that you will be able to hear a consumptive canary cough,” he said colorfully, but then added, as a preliminary explanation for the lack of further action, “Of course, most of the underworld has scuttled off to hiding places. It will be hard to find them, but we will never rest until the criminals are caught and Chicago is free of them forever.”

The next day, a newspaper editorial remarked sadly, “These gangs have run the town for many months and have strewn the streets with the lacerated bodies of their victims. Commissioner Russell and Deputy Commissioner John P. Stege have had their opportunity to break up these criminal gangs, who have made the streets hideous with bleeding corpses. They have failed.”

Russell replied to the charges, “My conscience is clear. All I ask is that the city will sit tight and see what is going to happen.”

   

All that actually happened was that Russell and Stege, in the words of the newspaper, “staged a mock heroic battle with crime by arresting every dirty-necked ragamuffin on the street corners, but carefully abstained from taking into custody any of the men who matter.”

   

Meanwhile, some of the blanks that had remained in the accounts of Lingle’s character and lifestyle began to be filled in. It is fair to say that the management at the Tribune was unaware of them, or they likely would not have turned Lingle into the martyr that they did. Some of the facts that had remained so far unmentioned were that he had himself hinted that he was the man who fixed the price of beer in Chicago; that he was a close friend of Al Capone and had stayed with him at his Florida estate; that when he died he was wearing a diamond-studded belt buckle that had been a gift from Capone; that he was on improbably friendly terms, for a newspaper reporter of his lowly status, with millionaire businessmen, judges, and county and city officials, and that he spent golfing holidays and shared stock market tips with the police commissioner – a boyhood chum whom Lingle had helped elevate to his current position in 1928.

By the time a week had passed, certain reservations had started to temper the anger about the newspaperman’s slaying that had been displayed on the front page and in the editorial columns of the Tribune. As more details about Lingle’s extracurricular activities began to emerge, McCormick and his editorial executives began to back-pedal away from their earlier statements and demands. Rumors about Lingle’s background and liaisons were racing around Chicago, supported by muckraking stories in other newspapers, and the Tribune began to take a different stance. They admitted that Lingle was apparently involved in some unsavory activities but they noted that the gangsters who killed him were still out there – and they still needed to be brought to justice.

McCormick’s investigators, as well as the police, had learned a lot about the background of Jake Lingle, a semiprofessional baseball player from the slums who had wormed his way into the lowest levels of Chicago journalism. His first job after leaving a West Jackson Boulevard elementary school was as an office boy at a surgical supply house. He was playing semiprofessional baseball at the time and he met William Russell, at that time a police patrolman, with whom he struck up a friendship. Lingle was hired as a Tribune copyboy in 1918. He had no aptitude for writing, but it was his long list of contacts (mostly made through Russell) and timely telephone calls to the city desk that made him indispensable to editors and rewrite men. The brash and cocky reporter cultivated acquaintances in the courts, the jails and in the gin mills of the North and South sides. Relying on the word of informants and friendships, he became one of the city’s least-known but cleverest crime reporters. He also became one of the wealthiest but whether this was from his dealings in the stock market, his investments in gambling clubs on the North Side, or from some other source is unknown.

Some believed that Lingle operated as a liaison between the underworld and the city’s political machine. Many out of town newspapers were referring to the slain reporter as the “unofficial Chief of Police,” who, for a sum, was able to “put the fix” in for gamblers, bootleggers, and anyone else who was having a problem involving law enforcement. Among the city hall insiders with whom he maintained a close relationship wias attorney Samuel A. Ettleson, the corporation counsel for Chicago and an operator in city government.

 Al Capone confirmed that Lingle was “one of the boys” during an interview in Florida in July 1930. He said that Lingle was a friend and that he didn’t have any sort of disagreement with him that led to his death. Capone also stated, “The Chicago police know who killed him.”

The question of who killed Jake Lingle was temporarily forgotten during exposure of his fascinating financial affairs. In addition to the secret bank account that Lingle kept with the Lake Shore Trust and Savings Bank, he was also known for carrying large sums of cash in his pocket. He had $9,000 dollars on him the day that he was killed. Another interesting branch of his activities that came to light were his “loans” from gamblers, politicians, and businessmen. He had “borrowed” $2,000 from Jimmy Mondi, a Capone gambling operator in Cicero and the Loop, -- a loan that had never been paid back. He had also borrowed $5,000 from Alderman Berthold A. Cronson, nephew of Samuel Ettleson, who later stated that the loan was a “pure friendship proposition.” That loan, too, had never been repaid He also had $5,000 from Ettleson himself, who only said that he had never loaned money to Lingle but often gave him some small remembrance at Christmas. He had a loan of $2,500 from Carlos Ames, president of the Civil Service Commission, that Ames stated was a “purely personal affair.” He had $300 from Police Lieutenant Thomas McFarland, who said that he had given Lingle the money because they had been close friends for many years. It was also alleged that Sam Hare, a roadhouse and gambling parlor operator, had “loaned” Lingle $20,000. Hare denied it.

Investigations also revealed that Lingle had been in an investment partnership with his old friend, William Russell. The account, used for stock market speculation, was opened in November 1928 with a $20,000 deposit. On September 20, 1929 – preceding the market crash in October – their joint paper profits were $23,696. Later, a loss of $58,850 was shown. Lingle showed paper profits at a peak of $85,000 that, after the crash, were converted to a loss of $75,000. Russell’s losses were variously reported as $100,000 and $250,000.

As to the source of the money put up by Lingle and deposited by him into his bank account, investigators noted, “We have thus far been able to come to no conclusion.”

But the press and the public had come to conclusions – and they were painfully obvious ones, which again confirmed that they were the residents of a city that was governed by dishonorable leaders and corrupt officials. The newspapers theorized about why Lingle had been murdered, but the fervor, and righteous anger, had waned. The unofficial verdict was that Lingle had “asked for it,” so to speak, by becoming involved with gangsters and dirty politicians.

Most theories of his death identified Lingle as a favor-seller and most placed the blame on Capone’s opposition, the Moran-Aiello merger. One story that made the rounds in gangland was that Lingle had been given $50,000 to secure protection for a West Side dog track, that he had failed to do so and kept the money.

   

Another story implicated him in the re-opening of the Sheridan Wave Tournament Club, which had been operated by the Weiss-Moran gang, but which, after the St. Valentine’s Day Massacre, had closed. Moran worked for eighteen months to try and find sympathetic officials to help him re-open the club, giving the job to Joe Josephs and Julian “Potatoes” Kaufman. It was said that Kaufman, an old friend of Lingle, had approached the reporter and asked him to use his influence with the police to get the club open again. Allegedly, Lingle   agreed to do so – but only if he were cut in on the action. He demanded fifty percent of the profits but Kaufman refused. Lingle then allegedly retorted, “If this joint is opened up, you’ll see more squad cars in front ready to raid it than you ever saw in your life before.” In spite of this, the story said, the club was permitted to re-open anyway. It was widely advertised that it would be opening on June 9 – the day on which Lingle set out for the races for the final time.

   

An equally plausible story stated that he got too deeply involved in the struggle for money and power in the gambling syndicate. For years, there had been a bitter war between the General News Bureau, a racing news wire service that existed entirely for the purposes of betting, and the independent news services. As an appointed intermediary, Lingle brought the two opposed factions together in January 1930 and a two-year truce was agreed upon. The truce, it was said, may not have extended to Lingle.

Perhaps some of these stories were true, or perhaps all or none of them were. Whatever the reason behind his murder, Lingle likely just got mixed up in the violence and bloodshed of gangland, an arena where even the most experienced can sometimes be torn apart.

The biggest question remained – who pulled the trigger that ended the reporter’s life?

Weeks, then months passed before the police produced a suspect. The serial number on the handgun that the killer had dropped had been filed off, but ballistics expert Colonel Calvin Goddard traced the origin of the gun to a sporting goods store owned by Peter Von Frantzius on Diversey Parkway. Records showed that the gun had been sold to Frankie Foster, a member of the North Side Moran gang. Foster fled to Los Angeles after the Lingle shooting, but was indicted in Chicago as an accessory before the fact to murder. Foster, whose real name was Frank Citro, was eventually extradited to Chicago and was held in the county jail for four months before the evidence against him was deemed inconclusive and the charges against him were dropped.

   

A short time later, a new suspect was named. Leo Vincent Brothers, a labor union slugger from St. Louis, was arrested in New York and indicted for the Lingle murder. Brothers had started out as a member of Egan’s Rats and soon graduated into labor racketeering and contract murder. Dodging a 1929 murder indictment, Brothers fled to Chicago, where he found work with Al Capone. Brothers was convicted and sentenced to fourteen years in prison for killing Lingle on April 2, 1931.

“I can do that standing on my head!” Brothers quipped after the sentence was handed down. Most observers, then and now, believe that Brothers was handed up to the state by Al Capone as a sacrifice, taking the fall for Jack Zuta, a racketeer who ran a string of whorehouses. Zuta was already dead by the time the trial wrapped up.

It seemed that just about everyone had a motive to kill Jake Lingle, but crime historians are in general agreement that Brothers took the rap and served time for a substantial cash payoff – but we’ll never really know for sure.

After his release in 1940, Brothers returned to St. Louis, beat his original murder case, and became hooked up with the local mob. Three months after an abortive attempt on his life, Leo Brothers died of heart disease in St. Louis on December 23, 1950. He took the secrets of the Lingle murder with him to the grave.

The story of Jake Lingle and all of the Chicago gangster murders, violence and ghosts can be found in Troy Taylor’s book BLOOD, GUNS & VALENTINES, available from the website in a print edition or as a Kindle edition from Amazon.