January 01, 2018

Article at Neil on Authory

Double-Crossing Capone

By Neil Root

(Published in Real Crime magazine)

To turn against Al Capone, the most powerful mobster in the world in the 1920's and early 1930's, was a brave or foolhardy move, and a deadly one, as one business associate found out

Arriving in Chicago at the age of twenty from Brooklyn, New York in 1919, escaping a murder rap there at the invitation of his cousin Johnny Torrio, Alphonse Capone was already a graduate of the notoriously vicious Five Points Gang, and a hardened criminal. Going to work for Torrio, who in turn worked for the flamboyant Chicago brothel and gambling kingpin ‘Big’ Jim Colosimo, Capone was well-placed in the Chicago underworld when Torrio had Colosimo rubbed out in 1920, Prohibition kicked in with the Volstead Act and the business-headed Torrio and his protégé Capone went into bootlegging, which Capone would later call ‘a public service’, as the vast majority of Chicagoans had never wanted to go dry.

But the increasingly highly lucrative bootlegging racket would mean violent gang wars, including against the Southside O’Donnell’s, the ‘Terrible’ Gennas and their ‘alky’ cooking business in their base in Chicago’s Little Italy, and above all the Northsiders, led by the smiling, trigger-happy and psychopathic Irishman Dion O’Banion. Capone, on his own after Torrio retired from the frontline in 1925 after an almost fatal assassination attempt by the Northsiders, would take them all on, killing O’Banion, his successors Hymie Weiss and Schemer Drucci along the way, and many others, to gain full control of the Chicago gangs, when tommy-guns were known as ‘Chicago typewriters’-rat-a-tat-tat- and the Capone gang controlled, through graft or bribery ‘on the payroll’, the police, judiciary, and even the Mayor of Chicago, the unprincipled and openly corrupt ‘Big Bill’ Thompson.

Chicago was Al’s town, often called Caponeville at that time. Added to the bootlegging racket were gambling and horseracing, prostitution, labour racketeering and protection/extortion. But it was a murderous town, with mob hit after mob hit, and even the infamously ruthless New York mobster Charles ‘Lucky’ Luciano remarked, after visiting Capone in the city in the late 1920’s, that it was ‘a goddam crazy place’ and that he hadn’t felt safe on the streets, with Capone himself going everywhere surrounded by bodyguards and triggermen, and being driven around in his custom-built armour-plated Cadillac, Capone himself surviving several assassination attempts, including a drive-by, car chases and poisoning. But in the end, it wouldn’t be poison or a bullet that took down Capone, but a betrayal, from a business partner.

Going to the dogs

One of Al Capone’s great passions was gambling, and eight bookmakers would later reveal on oath under fear of perjury that in 1924 Capone had paid over $12,000 to them, and by 1929 this had risen to $110,000- huge sums then, and testament to the fact that Capone was neither a lucky nor studious gambler. He was frivolous when placing bets, but the massive income from his rackets meant that he could afford it, and his profits from racing and gambling interests alone covered his losses many times over. By the mid-1920’s, when his gang was really starting to gain dominance in Chicago, he was investing in horseracing tracks, and by the late 1920’s he became involved in greyhound racing too.

Dog racing had started significantly in America in the late nineteenth-century, and by the roaring twenties it was really becoming established, with a regulatory (though not stringent) and promotional body overseeing it, and dog tracks opening in and around major cities. It was a working man’s gambling sport, though still in the shadow of baseball even after the New York gambler Arnold Rothstein fixed the 1919 World Series of baseball. Greyhound racing and gambling was soon gaining in popularity. Chicago was no exception, having the Hawthorne Kennel Club, located in Capone’s stronghold of suburban Cicero, where Torrio and Capone had built a thriving brothel and bootlegging empire when forced to retreat from central Chicago when the far less sympathetic Mayor Dever was elected, temporarily ousting the Caponeite ‘Big Bill’ Thompson.

The attraction of investing in a dog track was obvious to a man of Capone’s business acumen. It was much cheaper to keep and train dogs than horses, track overheads were far lower, and of course there were no jockeys to be paid and retained. As he might have said, it was a ‘swell’ opportunity to maximise profits at little outlay risk, and with greyhounds often starved or doped before races, the fix was often in. But Capone wouldn’t buy nor run the Hawthorne Kennel Club alone: someone with dog track expertise and a unique selling point approached him. Enter Eddie O’Hare.

Doing Business with Big Al

Also known as ‘EJ’, Easy Eddie’ and ‘Fast Eddie’, O’Hare was a native of St Louis, Missouri, where he practised as a lawyer. A big, forceful and gregarious man, O’Hare was only too happy to make moral compromises and deal with unsavoury and ‘heavy’ characters if there was the promise of financial gain. Besides, he had a daughter, Patsy, and a son to support, later nicknamed Butch. The father doted on his son, and was trying to turn him into a high achiever, not like his opportunistic self, but as a naval man, very much wholly respectable. O’Hare senior was far from respectable in his methods, legally representing shady characters from the St Louis underworld, gaining a reputation for getting defendants off hard charges, nothing being impossible for Easy Eddie. But counting your fingers would surely have been a wise move after shaking O’Hare’s well-manicured hand.

By the late 1920’s, O’Hare was expanding his interests into business, and his association with a former client, Owen T Smith, a bigwig in greyhound racing, who had invented a mechanical rabbit to act as a metaphorical carrot to keep the dogs focused and running, just as the electronic hare does at British dog tracks today. O’Hare saw his connection with Smith as his route into the business big time, and he became a minority partner to Smith in his dog track and mechanised rabbit licensing business. When Smith died suddenly in early 1927, O’Hare obtained full ownership of Smith’s rabbit patent by dubious means, and set about capitalising on it, first in St Louis, and then in Chicago.

On a visit to the Windy City, O’Hare came across the Hawthorne Kennel Club, and approached Capone, through intermediaries, to buy it with him. Capone agreed, seeing the financial potential, and it would indeed reap them both huge profits, and to be a partner in an outwardly legitimate, although really only a partly-legitimate business, must have been appealing to the already infamous Capone who was by now attracting national, and soon international, headlines. Above all, O’Hare owned the mechanical rabbit concept, and Capone knew the importance of that in greyhound racing.

O’Hare ran his dog tracks ruthlessly, sometimes appearing in court to defend his operations, such as gambling at tracks in Chicago temporarily became illegal, and O’Hare won the right to continue dog racing with the defence that punters were merely making ‘contributions’ to the upkeep and running of the greyhounds, rather than gambling. The fact that he was able to convince a judge of this should have been the ultimate proof of Easy Eddie’s alpha articulacy, razor-sharp brain and manipulative charm, but in reality. With Al Capone as a silent partner- Al and O’Hare very rarely had personal contact- it wasn’t such a feat, as that judge may very well have been on Capone’s payroll.

The Capone-O’Hare partnership thrived, and O’Hare undoubtedly benefitted hugely in terms of power and clout from his business association with Capone. But being associated with Capone could make you rich and other you protection, but it could also be a dangerous business, making you a target too, both from the authorities and rival gangs, but O’Hare was willing to take those risks. But O’Hare told his daughter Patsy that he didn’t feel morally compromised by working with Capone, a murderer by his own hand and behind ordering multiple gangland hits, even though Big Al was never convicted of that offence, everybody in Chicago knew. But on a more practical level, Easy Eddie said that he never accepted any freebies from the Capone gang, ‘not even a glass of beer’, as he didn’t want to owned, but just make and receive the dog racing profits to which he was entitled because of his hard work.

This business arrangement could have gone on for years more, but by 1930, the heat was finally coming on Capone from the Federal Government, with President Herbert Hoover himself said to have taken an interest in Capone, who was becoming the victim of his own success and flamboyance, the first ‘film star’ gangster, and indeed, Hollywood would make two films based on him in the early 1930’s- Little Caesar and Scarface. But above all, it was the St Valentine’s Day Massacre of 1929 which really put Capone on the spot. The brutal slaying of seven of the Northside gang- its’ then leader George ‘Bugs’ Moran being the missed target- in a Chicago warehouse, all of whom had been disarmed before being shot through the back with tommy guns and shotguns, made international headlines, and the authorities knew that they now had no choice but to crack down on Capone.

But Capone wouldn’t go down for murder, or any of his rackets- this would be hard to prove. The Inland Revenue Service (IRS) realized that they could go after him for tax evasion, although first they needed proof of his income year after year, and therefore non-payment of income tax. A chink in Capone’s heavy armour was needed, and as his business manager Jake ‘Greasy Thumb’ Guzik had been very careful to cover the financial tracks of Capone’s empire, an inside informant was needed. Enter Eddie O’Hare once again.

The Double-Cross

Frank Wilson was tasked with leading the tax investigation into Capone. Thin and bespectacled with the look of an accountant, Wilson was also wily, cunning and analytical, just what was needed to track down Capone’s elusive income sources so as to estimate the amount of backdated tax he owed, and then launch a prosecution that would put Capone, now the first Public Enemy Number One, in prison. Wilson used an unusual tactic- knowing that Capone was fond of talking to newspaper reporters, and that hacks all over the American Midwest were constantly thirsty for Capone-related scoops, Wilson went to John T Rogers, who covered the crime beat on the respected St Louis Post Dispatch, O’Hare’s hometown. But Rogers had also exposed other bootlegging gangs, and had been following Capone stories in Chicago, and knew a great deal of inside information about the mobster and his associates.

Rogers immediately gave Wilson a name, a man who had been doing business with Capone, and who must know something about who controlled Capone’s finances: Eddie O’Hare. Wilson then needed to convince Easy Eddie to spill, which could be a suicidal move for O’Hare. A low-level financial link in the Capone organization was needed to turn State’s Evidence, as Jake ‘Greasy Thumb’ Guzik was much too far up the Capone gang pecking order, being within Capone’s fiercely loyal inner circle, along with Al’s brother Ralph, Frank Nitti, ‘Machine Gun’ Jack McGurn, Frankie Rio, Frank Diamond and several others. Wilson hoped that O’Hare could lead him to that missing revenue link.

The journalist John T Rogers took Frank Wilson to meet O’Hare at the Missouri Club in St Louis. O’Hare was surprisingly easy to persuade. Firstly, he too would be implicated in Capone’s criminal affairs, and his own tax affairs were probably not in order. He also had no long-built loyalty to Capone, as they were just business partners and had had very little face-to-face contact, and the provably unscrupulous O’Hare may have reasoned that if Capone was incarcerated, he could take full control of their business. Another key reason may well have been that O’Hare was desperate to get his son Butch into the prestigious Annapolis Naval Academy, entry to which required a reference of recommendation from a US Congressman. If he informed, could Wilson swing it for Butch to get into naval school. Butch did later attend Annapolis, and this theory is very plausible.

Although most serious gangsters, let alone businessmen, would never have dared go against Capone with the Feds, O’Hare began to sing to Wilson, who would later write in his memoirs that O’Hare was ‘one of the best undercover men I have ever known.’ On top of saying that Wilson could inspect the Hawthorne Kennel Club financial records for any irregularities caused by Capone’s henchmen, O’Hare told Wilson that Capone’s men regularly wired profits to Miami, where Capone famously had his holiday home at Palm Beach., and in Miami the bagman who collected the dough was one Parker Henderson Jnr. Added to this, Easy Eddie named two Capone bookkeepers, Leslie Shumway and Fred Ries, who apparently had inside knowledge of the inside financial workings of the Capone empire- how much was coming in, and where it went.

Both Shumway and Ries turned evidence against Capone in return for immunity and witness protection, when told by the Feds that the Capone mob would probably kill them if they didn’t, as knowing so much they would be too much of a liability to remain alive. Nervously, they had to accept, and the evidence they supplied allowed Wilson and his investigative team to trace large amounts of money which had been earned illegally and no tax paid on it, running back to 1924, with the amounts increasing annually as Capone’s grip on Chicago grew. But O’Hare wasn’t finished yet.

When Capone finally went before the Federal Court in Chicago in the autumn of 1931, Easy Eddie told the Feds that the Capone gang had bribed and intimidated the jury, as was their custom, and at the last minute the judge swore in a new jury before the fix could be put on it. Although Wilson’s team had only managed to uncover a fraction of the gang’s true illicit earnings to court evidence standards, Capone went down for ten years for evading tax, to get him off the streets where he was far too powerful to control, and also to send a message to other gangsters that their earnings were taxable.

Capone began his sentence in the cushy Cook County Jail, where he had considerable clout, and was then transferred to the tougher Atlanta Penitentiary, before being sent to the newly opened and hellish Alcatraz, the island prison in San Francisco bay, where Capone’s syphilis, which he had contracted from a prostitute in his Chicago heyday, slowly went to his brain. When Capone was finally released early due to his mental and physical deterioration, even the loyal Jake Guzik told a reporter that Big Al was now ‘as nutty as a fruit cake.’

Eddie O’Hare continued to thrive, building up his business interests, becoming a wealthy man, proudly watching his son Butch become a naval cadet and then train as a pilot. And throughout the 1930’s, Easy Eddie continued to snitch to the Feds, either a very brave man or one who didn’t care about his own safety.

Serve it Cold

On the morning of Wednesday, 8 November 1939, eight years after he had ratted on Capone, Eddie O’ Hare, wearing an expensively smart three-piece grey suit and hat, came out of his office at the Sportsman’s Field track in Cicero, Chicago, climbed into his highly-polished black Lincoln-Zephyr coupe automobile and drove away. When he reached Odgen Avenue, he continued to make his way towards the crossroads between with Rockwell. But he never made that crossing.

A dark sedan car came up next to him, and two over-coated and hatted triggermen fired a rapid volley of heavy slugs, later found to be ones used to kill big game, into Easy Eddie’s car, hitting him numerous times, killing him instantly and leaving him a bloody mess. O’Hare was forty-six years old. O’Hare’s Lincoln continued to go as he died and smashed into a lamppost at speed. His two killers sped away down Odgen Avenue and disappeared. It was a classic gangland hit, Capone-era Chicago-style. Nobody was ever caught or prosecuted for Eddie O’Hare’s murder. But just eight days after his murder, Al Capone was released from prison.

A well-maintained Spanish .32 revolver was found in O’Hare’s car, and those who knew him well said that it was unusual for Easy Eddie to carry a gun, although it was hardly a high-powered weapon. Was he nervous or had he been threatened? No proof has ever been found, but he had every right to be nervous, for his betrayal of Capone and continued informing, a cardinal sin to the fellas of the underworld, and many had been killed in Chicago in the twenties and thirties for far, far less.

Numerous motives for O’Hare’s rub-out were mooted in the newspapers, but it soon became clear to most that it was almost definitely the Capone mob, an act of revenge for Big Al, a welcome home present. Capone would retire to his Miami home to be with his wife Mae and son Sonny and other family members, including his mother Teresa and sister Mafalda. Al Capone died in 1947, and he was buried in Mount Carmel Cemetery in Chicago, just a short walk away from the graves of Northsiders Dion O’Banion and Hymie Weiss, whose murders he had ordered, and other Chicago hoods.

Eddie O’Hare’s son Butch went on to become a war hero, shooting down numerous enemy planes in the Pacific and coming to the aid of other members of his squadron while under heavy fire in the air. He received the Congressional Medal of Honor in April 1942 from President Roosevelt. Butch was later shot down in action and Chicago’s airport was renamed O’Hare International Airport in his honour. Many believe that his father’s government connections sealed this dedication, but he was a bona fide war hero, and the Chicago Tribune newspaper had campaigned for the honour to go to him. Eddie O’Hare had paid the ultimate price for turning against Al Capone and had a violent death, but he would have been proud of his son.

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