Sometime around 1915 "Terrible Tommy" O'Connor brought Tommy Touhy, and his brothers, Johnny, Eddie and Joe into the fold of organized crime. O'Connor was an interesting character. Both he and his brother, "Darling Dave" O'Connor, once studied for the priesthood in their native Ireland. Terrible Tommy ended up as a graduate of the Valley Gang. Many even say that he was the true leader of the gang before Druggan and Lake converted it into a Capone satellite.
The O'Connors were primarily burglars, and, like the Touhy brothers, ran a taxi service as their cover since it allowed them a legitimate reason for being in any neighborhood at any time of the day or night. It was the O'Connors who introduced Tommy and the older Touhy boys to their true love, nitroglycerin. The Touhy boys used nitro to blow safes while they were active criminals between 1900 and 1924.
O'Connor was also dubbed "Lucky Tommy" because he seemed to always get away. But Tommy's luck ended one muggy Chicago night, when he and others burgled the safe at the Illinois Central Station and in the process somebody shot and killed the night watchman, Dennis Tierney, an off-duty Chicago policemen.
Although O'Connor and a hood named Jimmy Howard escaped, one of O'Connor's men, Harry Emerson, was captured. Emerson informed the police that it was O'Connor who fired the fatal shot that killed young Officer Tierney. He offered to tell that story in court in exchange for consideration and the State's Attorney agreed.
On November 12, 1919, O'Connor was arrested on robbery charges and promptly offered to cut a deal with the police. He would finger Harry Emerson as the cop killer but the States Attorney turned down Tommy's offer. O'Connor, who had dozens of childhood friends on the force, heard about the deal that Emerson had cut and decided that Emerson had to die before he went to trial.
O'Connor offered $200 to a childhood friend named Jimmy Chjerin if Chjerin would take the money to a hood named "Big Joe" Moran as a down payment for the assassination of Harry Emerson. Chjerin refused the offer, telling O'Connor that he had promised his father he would go straight.
"The Peacock of the underworld," as the papers called Chjerin, was a tough guy with a long record which included a stint at Bidwell Prison. He got away with most of his minor crimes because the cops liked him, and because his father Dominick Chjerin was a municipal court bailiff and saw most of the beat cops several times a week. The Peacock's father tried to keep his son out of trouble but when that failed, he fixed the records for him or called in a favor from the cops to let his son walk away from a charge.
But the cops and judges were growing tired of looking the other way. Jimmy the Peacock, they said, was out of control. Then Jimmy impregnated his girlfriend. In an effort to do the right thing he married her. When their child was born Jimmy the Peacock swore to his father and wife and infant son that he would change his ways and go straight. This is why he turned down Tommy O'Connor's orders to take the murder money to Big Joe Moran. The only problem was that O'Connor didn't take disobedience in the ranks lightly. O'Connor was worried that the next time Jimmy the Peacock got into trouble he might tell the cops what O'Connor had asked him to do.
The Peacock didn't worry about it very much. The cops had O'Connor on a rock-solid charge of murder with an eyewitness.
Then, friends bailed out Terrible Tommy O'Connor.
On January 21, 1919, Jimmy Chjerin was sitting in the back seat of a stolen Model-T Ford with Tommy O'Connor. A Valley hood, Louie Miller, was sitting in the front seat. The three of them were laughing and joking when suddenly O'Connor stopped laughing, turned to Jimmy the Peacock and pumped three shots from an army service revolver into the young man's temple. Jimmy the Peacock died immediately. O'Connor barked at Miller to drive to Stickney, a town just south of Chicago and find an empty ditch where they would dump the body. Miller did as he was told.
Six months later Jimmy The Peacock's young widow turned on the gas in her coldwater flat, killing herself and her infant daughter and Jimmy the Peacock's father swore revenge against O'Connor. Using his own criminal connections, Jimmy's father had O'Connor's driver, Louie Miller, kidnapped from a Montrose Avenue saloon and brought to police headquarters where, after a beating, he swore that he had seen Tommy O'Connor gun down Jimmy the Peacock. Detectives picked up Tommy O'Connor and booked him for murder.
On January 8, 1921, acting on a tip from the Chicago Tribune, the police grabbed Louie Miller at his sister's home. He was wearing only underwear and was clinging to the edge of the second floor window when the police dragged him inside and hauled him downtown for another beating and more questioning. Again Miller gave a sworn statement that it was Tommy O'Connor who killed Jimmy the Peacock and once again the cops arrested O'Connor for Jimmy the Peacock's murder. This time they had him. But O'Connor was able to post the $45,000 bail, which was the largest bail ever required in Chicago at that time. O'Connor disappeared as soon as he was released.
On March 23, 1921 Detective Sergeant Patrick O'Neill got a tip that O'Connor was hiding out at the home of his brother-in-law, William Foley, at 6415 South Washtenaw Avenue. Five detectives circled the house and O'Neill called inside for Terrible Tommy to surrender. O'Connor burst through the door, guns blazing and yelled "Well, I'll get one of you anyway!"
Officer O'Neill was standing in the center of the yard and was taken off guard by the suddenness of the attack. O'Connor cut him down before he could point the pistol in his hand. Detectives Tom McShane, Joe Ronan and William Fenn started shooting the very second O'Connor raced out the door and assumed that they shot O'Neill by mistake. Badly rattled the detectives stood over O'Neill's body weeping "Joe! Joe! Oh God!"
O'Neill would lie in his own blood for fifteen minutes, twisting in agony before the ambulance arrived and rushed him to St. Bernard's hospital where he died. Meanwhile, Tommy O'Connor leaped over a fence at the rear of his sister's yard and ran down 63rd and Western where, at gunpoint he leaped into a checkered cab and was driven a mile before leaping out. He commandeered another car driven by William Condonn who drove O'Connor to Stickney where one of his men ran a saloon. There he was provided with clothes and food.
The search for O'Connor was one of the greatest manhunts in the history of the city. The search by an angry police force went on for days in the city and the suburbs, but the cops came up empty. Then a report arrived that O'Connor had been seen at the Crystal Palace dance hall on the far south side. Cops raided the place while O'Connor was dancing the shimmy with some girls.
"Throw 'em up, Tommy!" the cops shouted.
There was chaos. The hall emptied quickly, some of the dancers were pressed against the wall and searched but O'Connor once again slipped away to freedom. It was rumored that O'Connor was dressed in women's clothes so as to make an easy escape.
The cops finally caught up with O'Connor on July 25, 1921. He was arrested with a Valley hood named Jimmy Gallagher in Minneapolis after an unsuccessful attempt at robbing a Pullman car on the Chicago Great Western passenger train bound for Omaha. As an extra embarrassment, the most wanted man in America was captured by a switch operator named W.L. Woods who was only armed with a hammer at the time.
A squad of heavily armed detectives was sent to St. Paul to bring O'Connor back to Chicago. It was an illegal transport, but since O'Connor was a two- time cop killer, no policeman in Chicago or St. Paul really cared about his civil rights. However, the state of Minnesota was charging O'Connor with an earlier payroll robbery and wanted him to stay in their state to stand charges. But the Chicago cops took O'Connor out of the city with such speed that the City Attorney, Floyd Olson, formally charged the Chicago Chief of Detectives with kidnapping. He sent three carloads of his detectives to bring O'Connor back but they were turned away at the city border.
On the way back to Illinois, O'Connor told the cops "It wasn't my revolver that killed him. He [Officer O'Neill] was shot down by his own pals. It was a mistake of course, but they shot him and after that mistake they ran away and put the blame on me. Do you wonder why I ran away? What chance did I have with every policeman in the city out to get me dead or alive? Me, the con, only a hundred and thirty-eight pounds? I never shot anybody, at least not to kill, in my life."
He said the same thing in court but nobody was listening then either. On September 24, 1921, O'Connor was found guilty of first degree murder and was sentenced to be hanged. The date of execution was set for December 15, 1921. When the judge read the verdict, there was a cry from O'Connor's father who was sitting with his other son, Darling Dave. Since his time working as a hood with Tommy, "Darling Dave" O'Connor had become a LaSalle Street investment broker. However, he lost his license for immoral conduct in 1919. "It's the wrongest [sic] verdict in the world," he told reporters about his brother's sentence, "we couldn't get justice, we couldn't get justice."
On October 15, 1921, Judge Kickham Scanlan denied O'Connor a new trial and the decision and the death sentence stayed. O'Connor was ordered to be held in the criminal courts building until his hanging. From his cell there, he could hear the scaffolding of the hangman's platform being built.
On December 15, 1921, a man was seen driving his car to a street outside of the criminal courts building where O'Connor was being held. The man parked and then walked up and down the street outside the jail and then tossed a package into an open window. Most believe it was the guns O'Connor would use to escape that day.
O'Connor may not have needed the guns since it's commonly agreed that either he bribed his way out of his death cell or was simply let free by guards; one way or the other, his daring daylight escape was spectacular.
Tommy Touhy, who hung out with Darling Dave O'Connor at a saloon on Hoyne and Madison Streets in the Valley, boasted openly about providing the two guns for Tommy O'Connor's fabulous escape from prison. He even claimed that he had engineered the entire incident. However, another story was that the guns were smuggled into the jail by way of a pork chop sandwich. The guns were intended for another prisoner, but the jail's cook, William Fogarty, a convict himself, gave the weapons to Tommy's cellmate, a man named Charles McDermott.
Since it was a Sunday the prisoners were allowed to walk in the yard for their exercise. The guard on duty in the yard was David Strause who later reported that LaPorte and O'Connor stood up close to him while O'Connor said he was ill and needed a pass to the hospital.
When the guard bent over to write the pass, Laporte and O'Connor jumped him from behind and then O'Connor whipped out a pistol and stuck it into the guard's ribs while Darrow took his keys.
The other prisoners in the yard saw the escape and crowded around but O'Connor turned his gun on them and ordered them back into their cell blocks. Then, O'Connor and his four men ran down the stairs and overpowered guards Charles Moore, Thomas Jefferson and Thomas Wetta. They were all bound and gagged but not before Wetta managed to yell out, "Prisoner escaping!" alerting the other guards on duty.
On the run now, the prisoners scaled a wall by jumping on a shed and then over the 9-foot wall. Laporte, a heavy set man, broke both of his ankles as he fell and was quickly recaptured.
Darrow and McDermott fled in a different direction than O'Connor. They were recaptured by the police within a half hour. O'Connor escaped by leaping onto a passing car's running board. As he jumped, the clerk of the jail, Austin Jacobson, grabbed his coattail but let go when O'Connor spun around and pointed the gun at him. After the car turned the corner Tommy O'Connor was gone.
When questioned by police about the escape, Dave O'Connor, Tommy's father said "We knew the power of God would save Tommy and show the police and all the people that were against him that he was innocent. We're going to have a merry Christmas at our home now."
On December 17, 1921, the body of a man was found under a bridge three miles north of Palmyra, Wisconsin in rural Jefferson County. He had been shot with a .32-caliber revolver. The police theorized that O'Connor had forced his way into the man's car and then made him drive out across the state line. There, O'Connor found it more expedient to kill the man rather than face a kidnapping charge. The body was stripped of its clothes and wallet and left face down in the mud.
Then a note arrived from Milwaukee in Tommy O'Connor's hand "Chief: Don't send anybody after me. I am innocent. Much obliged to Struass. I am gone but my friends will reward him/Good luck to you all. I will be posted by friends and will shoot the first man who comes near me."
The Chicago police assumed O'Connor had hidden out in St. Paul and then slipped over the Canadian boarder before traveling to Ireland. However the last place that Tommy O'Connor was seen alive was in that tiny village of Elkhorn, Wisconsin, on December 10, 1922.