A number of mysteries still surround the ambush murder of Edward Joseph O’Hare on Chicago’s West Side on November 8, 1939. But one thing is certain; his assassination was a revenge for crossing Al Capone.

O’Hare was born and raised in the tough Kerry-Patch neighborhood of St. Louis who lucked into a fortune through dog racing. The inventor of the mechanical rabbit for dog racing was a St. Louis promoter named Oliver P. Smith. He first tested the device with greyhounds in 1909 and spent the next decade developing it. After he filed for a patent, he formed a partnership with a sharp, young St. Louis attorney named Eddie O’Hare. For the right to install a mechanical rabbit dog track, the owners paid Smith and O’Hare a percentage of the gate. Smith died in 1927 and under an arrangement with his widow, O’Hare obtained the patent rights for the metal rabbit. He became a major player in the racing world and an overnight millionaire.

He started his own dog track in Madison, Illinois, across the river from St. Louis, and founded the Madison Kennel Club. The money poured in until a series of police raids forced him to shut down. A Cook County judge, Harry Fisher, meanwhile, had come to the aid of the Capone outfit by declaring dog tracks legal and preventing the police from raiding them. The judge’s brother, Louis Fisher, was the lawyer representing the dog track owners. The Illinois Surpreme Court eventually overruled him, but for a time, Capone prospered with the Hawthorne Kennel Club, located on the outskirts of Cicero.

Unlike the later closely supervised legal sport, the dog racing of the 1920s was easy to fix, much to the dismay of innocent bettors. For example, if eight greyhounds were run, seven of them could be overfed or run an additional mile before the race, leaving the eighth dog as the almost guaranteed winner.

O’Hare despised the men that he had to work with, almost as much as he loved the money that he was making. However, he believed that there was money to be made working with mobsters, as long as he didn’t associate with them personally and kept all of his dealings professional.

But O’Hare had his own brushes with the law in his past. At the outset of Prohibition, the authorities permitted a liquor wholesaler named George Remus to store about $200,000 worth of whiskey in the same building where O’Hare had his law office. Remus had to put up a $100,000 bond as surety that he would not remove a single bottle without government sanction. Nevertheless, by 1923, all of the liquor had found its way into the bootleg markets of Chicago, New York and other cities, even though Remus never saw a cent of profit. Enraged, he filed charges and caused indictments to be filed against twenty-two men, including Eddie O’Hare. The lawyer was sentenced to a year in jail and fined $500, but won a reversal on appeal when Remus withdrew his original testimony. O’Hare, it was learned later, offered to pay off Remus to drop the charges against him.

O’Hare quickly made a name for himself in Chicago and earned the nickname of “Artful Eddie”. He was a well-mannered, cultivated and handsome man. A strong athlete, he rode, boxed, swam, and played golf. He never smoked and never drank hard liquor. Married young, he fathered two girls and a boy. His son, Edward H. O’Hare, nicknamed “Butch”, was twelve when his father first met Al Capone. O’Hare idolized the boy and more than anything that he wanted for himself, he wanted a great career and wonderful life for his son.

O’Hare decided to inform against Capone for paternal reasons. His son, Butch, was determined to attend the U.S. Naval Academy at Annapolis  and O’Hare wanted to smooth the way for him by helping the government bring down Capone and his organization. “If O’Hare had ten lives,” John Rogers later said, “he would gladly risk them all for the boy.”

Wilson heard from O’Hare frequently after that, either directly or through Rogers. It was O’Hare who told him about the structure of the Capone dog track management and verified that more than half of the profits went directly into Capone’s pockets. He also called Wilson one morning to warn him that Capone, acting against the judgment of cooler heads, had brought in five gunmen from New York with a contract to kill him. The contract called for a payment of $25,000, O’Hare told him, and the killers were driving a blue Chevrolet sedan with New York plates. Wilson heeded O’Hare’s warning and he and his wife immediately moved to another hotel. They told the desk clerks at the Sheridan Plaza that they were going to Kansas City, drove to Union Station, then circled back and took a room at the Palmer House. A twenty-four hour guard was assigned to look after them.

Capone went to prison but O’Hare’s undercover activity didn’t end with the Capone case. Despite his long and profitable association with gangsters, O’Hare had detested them from the start, and he went on informing against them to both county and state police, undaunted by Wilson’s warning that some policeman in the pay of mobsters would betray him. And Wilson was right – O’Hare’s secret would not remain hidden for long.

Ensign Henry “Butch” O’Hare graduated from Annapolis in 1937 and was sent overseas just after the attack on Pearl Harbor, which marked the United States’ entry into World War II. On February 20, 1942, he single-handedly saved the U.S. Navy carrier Lexington from certain destruction. The lone pilot attacked a wing of Japanese fighters and wreaking havoc on the enemy craft, he prevented an aerial bombardment of the fleet. For his bravery, President Franklin Delano Roosevelt awarded him with the Congressional Medal of Honor. More than a year later, in November 1943, Butch O’Hare vanished near Tarawa Island while establishing night radar flights. His body and plane were never found. On September 18, 1949, Orchard Depot, an isolated airfield on the far Northwest Side of Chicago was formally dedicated O’Hare Field in honor of the brave fighter pilot.

Unfortunately, the hero’s father never lived to see the recognition that was given to his son. The word had leaked out that Eddie O’Hara was an informant and the news reached even Al Capone, who was, by that time, serving time at Alcatraz. A team of gunmen were recruited from the Egan’s Rats gang of St. Louis and plans were set in motion to kill O’Hare.

It is thought that perhaps Frank Wilson’s warnings had made an impression on O’Hare. He was still enjoying considerable success in his professional life as the president of the Sportsman’s Park racetrack in Stickney, as a developer of legal dog racing tracks, manager of the Chicago Cardinals football team, real estate investor, and the owner of an insurance company and two advertising agencies. But in spite of his wealth and the respect that he earned as a business leader, he became a very paranoid man. Remembering Wilson’s words, O’Hare began carrying a gun with him every day. On the day he was murdered, though, he never even had a chance to draw it from its holster.

On November 8, 1939, O’Hare was driving from the dining room at the Illinois Athletic Club on Michigan Avenue to his office at the racetrack. He had no idea that his assassins were waiting for him at Twenty-Second Street and Ogden Avenue. As O’Hare drove past the intersection, a car pulled out and followed close behind him. Moments later, they pulled alongside him as he approached 2601 West Ogden. O’Hare clumsily tried to pull out his gun, but it was too late. Two men fired shotguns from the other car and Eddie was hit in the face and the head. The new Lincoln Zephyr automobile that he was driving swerved sharply, jumped the curb, rattled over the streetcar tracks, and smashed into a trolley pole in the center lane. The second car roared away and O’Hare’s killers were never found.

Inside of the wrecked car, the police found O’Hare’s handgun and the items in his pockets included a rosary, a crucifix, a religious medallion, a  love note to a girlfriend that he had written in Italian and a poem that he had apparently clipped from a magazine. “Margy, Oh, Margy,” the note read, “Quanto tempo io penso per te. Fammi passer una note insieme con te”.  [How often I think of you. Let me spend the night with you.]

The poem read:

The clock of life is wound but once

And no man has the power

To tell just when the hands will stop

At late or early hour.

Now is the only time you own.

Live, love, toil with a will.

Place no faith in time.

For the clock may soon be still.

It could have easily served as an epitaph for Eddie O’Hare.