John William Tuohy lives in Washington DC


Is it possible that Tommy O’Connor, the Irish mob boss from the Valley, leader of the Touhy gang who caused the largest man hunt in Illinois history lived out the last of his life under his real name in Chicago?

Early years

Tommy O’Connor was an interesting character. Both he and his brother, “Darling Dave” O’Connor had, at least according to legend, once studied for the priesthood, although considering O’Connor, overall, that seems highly improbable.
He was born the son of Joseph and Elizabeth (Nee Roach) O’Connor in Ireland in 1891 in Gardenfield, near Monagea, Limerick in a place called Scanlon’s Fields (Which is not a field but a geographic area. Locally the area is called Templenamona. )  in a house dubbed Moín a Ghédh, means 'The Bog of the Goose'.
The family arrived in Chicago in 1893 when Tommy was age two years old. His siblings included John, born in Ireland 1887. John like his sister Mary lived a legitimate life as a union electrician. A lifelong bachelor, he died in Elgin Ill in 1936.
Brother Dave, dubbed Darl’n Dave by the newspapers (It’s unlikely anyone ever actually called him Darl’n Dave. He was actually known as “Dapper Dave” along LaSalle Street where he worked) was also born in Ireland in 1889.  As a teen, David took a job as a mail runner on the Wheat Exchange for Logan & Bryan and eventually became a broker. He seemed to be going places until 1918 when he was arrested, tried and convicted for “immoral conduct”.
David and another man, a college professor (Professor of languages) friend named Louis Alberto. Several years before the incident, Alberto, who wore a frock coat and carried a cane) helped O’Connor out of a messy divorce when he told the court that he had kissed and fondled O’Connor’s wife, Ethel Rose. According to Ethel Rose, who married O’Connor in 1912, Alberto lured her to his apartment, got her drunk, had her dress in a kimono, turned on the Victrola and was dancing with her in the bedroom when Dave O’Connor and a police detective rushed into the room “Cathcing them in the act” (The couple were also seen at the Green Mill Tavern, later run by Machine Gun Jack McGurn)
Based on Alberto’s testimony (He worked out of an office at 4346 North Campbell Avenue in Chicago. The building is still there) which was backed up by the police detective’s testimony, O’Connor was exempted from alimony payments higher than $75.00 a month. During the divorce proceedings Ethel Rose told the court that O’Connor had carried on a multitude of affairs. She said that she had uncovered a batch of love letters from a young woman to her husband, with each letter referring to O’Connor as “My Darl’n Dave”.
 Now in 1918, O’Connor and Alberto were accused to taking a 15-year-old girl named Irene Meyers to a bar, getting her drunk and then raping her.  It took two trials to convict to a year in prison (and the temporary loss of his broker’s license) and the facts surrounding the case appear to support O’Connor’s claim that Miss Meyers was an extortion artist, mature far beyond her years.
 As much as anything, the public’s hatred for his flamboyant brother Tommy, widely considered an arrogant and merciless cop killer, convicted Dave O’Connor. The State Supreme Court later over turned the case but by then O’Connor was forced to sell his seat on the Exchange for $7,000 to pay his legal fees.
 He spent the rest of his life one the right side of the law, became a highly successful commodities broker, had completed a year of college and lived with wife (Gladys, whom he had met on the L on his way to work in 1916 while she was a student at the exclusive Belmont College for Young Women in Nashville Tenn. his parent and mother- in- law (Loubdda Heistand) in affluent Oak Park and later Maine, Illinois. (503 Golf Road)
 O’Connor’s father was, by all accounts, a loving family man who worked two jobs most of his life and early on saved up enough money to buy a modest house on West 13th Street near Paulina Street.  (An apartment house stands on the property today)

O’Connor and Jimmy Cherin

Despite his reputation as a lifelong thug, Tommy O’Connor was unknown to the police until he was 21 years old. He more than probably fell into a life of crime through his childhood friend, a tough hood named Jimmy Cherin whose father, Dominick Cherin was a political wardheeler who owned a saloon. The police held that the saloon was actually a front for the elder Cherin to fence for stolen goods and were certain that most of his customers were criminals.
In their late teens, Tommy O’Connor and the younger Cherin became regulars at Cherin’s saloon where they met Tribley Thompson a legendary criminal in the valley neighborhood took them under his wing and taught them how to steal cars.
Unlike O’Connor, Cherin became a protégée of Trilby Thompson and Eddie “Ammunition”” Wheed, largely because all three were said to indulge in opium and cocaine.

Eddie “Ammunition”” Wheed

On April 21, 1917 Wheed’s gang robbed a bar at 418 Wells Street, (It’s a parking lot today) murdering bartender Tommy Connolly without cause. The entire take was less than $300.00.
Then on July 13, 1917, Wheed and others robbed the Chicago City Bank and Trust at 6233 South Halstead, (It’s an empty field today) killing police officer Peter Bulfin in the process. (One of the four men was a thug named Big Danny Romano, a driver and go-fer for Barney Grogan, who was later suspected of hiding Tommy O’Connor after O’Connor’s prison escape. Another part of the robbery gang that day was Jimmy Cherin) Wheed later admitted that he also robbed the Winslow Brothers payroll robbery with four other men and that he took a cut of $2,500 from the hold up.
On September 1, 1917, Wheed stood off 250 Chicago policemen for two hours from a shack on his mother’s property on Thomas Street. When police finally forced him to give up, Wheed was found with several revolvers, a shot gun, a rifle, a battery of knifes 500 cartridges of steel jacketed bullets, 300 shot gun shells and two bottles of nitroglycerin. “This gun toting habit of mine” Wheed said “is the cause of my downfall.”
The incident later brought about the formation of the Chicago Crime Commission
Captured, Wheed wrote a diary, in underworld lingo, which he handed over to the States Attorney’s office, admitting to 30 robberies in Chicago and twenty more in other cities.  Most of the dairy was gibberish and mad ravings enough so that Wheed’s lawyer, Robert L. Cohan insisted that Wheed was insane and should be committed to an insane asylum. Wheed solidified that statement by rushing at several witnesses and wrestling with two bailiffs.
On February 15, 1918, at 9:00 in the morning Wheed was hung by his neck until dead. He went to the gallows cool and calm. Minutes before he was executed he told a reporter “I am an anarchist but I am a devout Catholic who believes in God. I go to church when there is no danger from the police. I say my prayers on my knees every night. But the world is upside down. It is filled with injustice. The rich have everything and the poor have nothing. I have never robbed a poor man. I am no cheap stick up artist who lurks at the mouth of an alley for chance victims who may not have more than 30 cents in his pocket. I rob only the rich who can afford to lose money. I play for the big game. I stake my life against the gold. If I lose I lose my life”

Frank Trilby Thompson

The other criminal mentor in Jimmy Cherin’s life was Frank Trilby Thompson, the leader of a car thief gang and convicted on a charge of armed highway robbery, escaped from Joliet prison in October of 1913 with a Valley crook named William Sunny Dunn and another hood named Vic Sander. Both Sanders and Dunn was where quickly captured. Thompson crawled out of shop window and made his way over the prison wall. The chief of police, who had the unfortunate name of Weeney, told his men to “bring in Thompson, dead or alive”
James Henry Higgins, a stick up artist who specialized in robbing bars was one of Trilby’s top men until he was shot and killed in 1913 while robbing Harry Martini’s saloon at Robey and Orden Streets in the Valley. (The bar had once been owned by Jimmy Cherin’s father, Dominick, although it is likely that Dominick still held a stake in the place) Higgins was also close to Jimmy Cherin and newspapers of the day reported that Higgins, Cherin and Tribley Thompson were “Kings of the walk” and were known for shaking down other burglars who worked in their areas of interest (Mostly large postal way lay stations)   
But even then O’Connor was well enough behaved so that in 1916, when O’Connor was 25 years old,  a burglar named Harry Fieldhouse was paroled from Pontiac Prison into the care of Tommy O’Connor whom the parole board found to be a “fit and decent citizen who would assist in (Fieldhouse’s) reform”
Physically there wasn’t much to Tommy O’Connor. He stood five foot seven and weighed 138 pounds. Dr. Francis McNamara, once the medical director of the Cook County jail recalled that O’Connor’s “hair stood up on his head like a crown or as if he had just seen a ghost. He had high inched eyebrows that gave him a constant startled expression.
 He always looked as if he was frightened and I believe he was most of the time. As the day fixed for his execution this look became more intense. He was a coward, of this I am certain. There were lines of nervous tension on his lean cheeks.
 He only fought when cornered, like a rat or when he could take his victim by surprise. Once, before he was famous, he threatened to kill a police officer on sight. Sargent Herman Otten.
Otten was a detective Sargent with the West 13th Street Station. On February 3rd 1913, Otten shot and killed Jimmy Higgins. Higgins and another hood named Billy Cantwell were robbing Harry Martini’s saloon at 2000 Ogden Avenue. (There is a green space to an office building there today). Reading the newspapers of the day it seems that Martini’s (Martini was Harry Martini, a convicted pick pocket) was robbed on a monthly basis.
 The pair were in the midst of forcing the bars customers into the freezer when Otten and a Detective Morrissey entered the bar. Higgins drew on the Otten but Otten fired first, putting a bullet through Higgins forehead. As for Billy Cantwell, he was beaten so severally he had to be taken to a nearby hospital. 
According to police Higgins and Cantwell were paid $25 each to rob the bar by Martini’s former business partners, the Gill Brothers. The Gills ran a successful bar with Martini at 1055 Ogden Avenue. Since Martini was a convicted criminal and unable to get a license to operate a saloon, the Gills held the license in their name, allowed Martini to run the bar and took most of the profits. Martini grew discouraged and talked a brewery in to paying to open his saloon on 2000 Ogden and placing the license in their name.
It wasn’t the first time that the Gills had paid to have Martini robbed.  On New Year’s Day, 1913, Trilby Thompson (Trilby was a regular at the Gils saloon. They even let him burn his prison uniform there when he escaped from Joliet in 1913) came out of hiding and robbed Martini’s at gunpoint at 3:30 in the afternoon. He also robbed the patrons telling them “Put em up and put up now, this is my busy day” including Police Detective George Garry. As Trilby fled out the back door, Garry pulled out his service revolver only to have the gun misfire twice. Garry, who said he thought at first that the robbery was a joke, said he was in the bar during working hours “On police business”
Trilbly was suspected of killing a cop during a daylight robbery in January of 1916 and Deputy Chief of Police Schuettler offered a $5,000 reward to anyone who would lead the cops to Trilby. In turn, Trilby sent Schuettler a note “Come and take me. I have consumption and I am dying but I would like to kill a few policemen first”
A small man like O’Connor but unlike O’Connor he was a brave man. O’Connor sent him a note promising to kill him on sight because he had arrested a bandit named (James) Higgins one of Tommy’s pals and mentors. The offcier put the note in his pocket and went in search of the young bandit. When he found him he deliberately spat in his face and then turned on his heel and walked away and O’Connor did not have the nerve to shot him, not even in the back”
O’Connors, according to popular opinion anyway, was also a burglar and, like the Touhy brothers who were his childhood friends, drove a taxi at night as a cover since because it gave him a legitimate reason for being in any neighborhood at any time of the day or night.

O’Connor’s other gang affiliations

It was, legend says,  O’Connor who introduced his friend Tommy Touhy, the future leader of the Touhy gang to his love of nitroglycerin which the Touhy Brothers  used to blow safes during their burglary years (between 1900 and 1924.) before prohibition turned them into bootleggers and killers. But again, although O’Connor’s childhood friendship with Tommy O’Connor is factual, there is no evidence that O’Connor was burglar.
Just prior to joining the so-called Emerson gang, O’Connor may have done some work with the Gloriana Gang, led by “Long Charlie”  Gloriana that was mostly Italian but occasionally allowed in an Irishman to round out their association of burglars’, stick up artists and  payroll robbers. O’Connor was also suspected in robbing the Southwest Side Saving Bank where police officer Edward Flynn was shot.
Tommy O’Connor met William Ray Emerson AKA “Babe” and Harry Harrison, at the Cherin’s saloon when Emerson was on the run after escaping from the Minnesota State Prison.  Emerson robbed the Illinois Central ticket office on Park Row in Chicago. Emerson put a gang together that included Abraham Schaffener a safe blower and bank robber. On August 14 1910 Schaffner, then a teen, was arrested on charges of horse thievery, burglary and swindle.
The others included James Hanraty a former prize fighter turned criminal and George Raymond a knock around guy who robbed the Astor Restaurant in 1913. A police detective leaped in Raymond way as he escaped and Raymond pulled out a revolver and pulled the trigger several times but the weapon locked each time.  A few weeks later he was arrested and convicted of attempted murder but somehow got the charge dismissed. At the end of the year he was arrested and convicted of robbery, served four years and was paroled with a clean record. A month later he killed a police man during a robbery of the Normal Avenue saloon at gun point.
At first Emerson said he played no role at all in the robbery that would lead to Tommy O’Connor’s downfall and that George Raymond killed Tierney and that the other involved were only Abe Schaffner and Willie Sharkey, a mentally unbalanced thug who later worked for Roger Touhy as a hired gun.
 Emerson said that the gang was planning another robbery the night before Tierney was killed and that Hanraty was the one who told them about the Illinois Central Railroad job. The original job may have been to rob millions of dollars in cash from the City Treasury in town hall.
Emerson said that after it was decided to rob the railway deport that they intended to steal a getaway car but that went awry so they walked to the taxi stand at Union  Station and hailed a cab driven by a young man named Jimmy Pelikan.
They arrived late to the depot, at 10:00. Cash collections at the depot started at 8:54.  Emerson said that he and O’Connor were supposed to jump the armed guard accompanying Tierney, a man named Quinney and that Raymond was supposed to handle Tierney alone. But Raymond arrived late so Emerson walked up to the guard and put a gun to his head and searched him but found no pistol on him. Quinney’s pistol was in a holster that had slide on to his back when Emerson grabbed him from behind and Emerson had only frisked the front of Quinney’s body. Quinney later identified O’Connor as “Very nervous and whistled through most of the robbery”
At the same time O’Connor jumped Tierney, the man carrying the cash, and struck him over the head with the butt of his gun and tried to wrestled him to the ground but Tierney was considerably larger than the slightly built O’Connor and easily put O’Connor on his back on the floor.  At that point all of the robbers had their weapons in their hands. Emerson joined the fray with O’Connor and beat Tierney over the head with his pistol.
Emerson said that O’Connor finally got control of the black leather money bag and ran out of the depot just as Raymond arrived. Emerson that he and O’Connor were out of the building by then and that they heard shooting.  However witnesses said that Tierney staggered to his feet drew a weapon and fired and that Emerson and O’Connor turned and returned fire. One bullet hit Tierney in the upper right breast killing him.
Leaping into the waiting cab, O’Connor yelled at the driver “Get the hell out of here and fast if you don’t want your head shot off” but Emerson put then a gun to his head and told him to follow orders. “Take orders from me and you’ll be all right” Emerson told the driver “If you don’t you’re a dead one I’ll croak you”
Seconds later, Emerson said, Raymond flew down the depot stairs with Tierney in hot pursuit. Raymond fell and tumbled down several stairs and Emerson leaped out of the car and pulled Raymond into the back seat and yelled for the driver to take off. At that second Quinney, the armed guard fired off a shot at them, emptying his chamber, probably grazing one of the robbers since a bloody cap was later found at the scene. Emerson returned fire and started screaming at the driver “Faster!” and a minute later they barely escaped a head on collision with a street car at Randolf and State Streets.  A block later O’Connor gave the driver $40, put the car in neutral and pushed him out of the car, took the wheel and floored it.
As they drove away Raymond said that “I threw five slugs at the guy (Tierney) and I think I bumped him off”  A few years later corrupt newspaper reporter Jake Lingle would also be murdered not far from where Tierney fell dead.
Emerson was renting a room in a boarding house at 4140 West Monroe Street run by Mrs. Tillie Sullivan who was lasted arrested for her role in a bank robbery that included George “Bugs” Moran.
After the robbery the gang gathered at Sullivan’s boarding house and divided up the loot (Emerson said he got only $350) on the kitchen table in front of Mrs. Sullivan.  They each tipped Mrs. Sullivan ten dollars and let keep the coins from the robbery and then they split up and he and Raymond had spent the night after the killing at the home of Big Tim Murphy after stopping to have Chop Suey at a restaurant on Paulina Street. Emerson said that Raymond was a friend of Murphy’s and that Raymond said to Murphy “Well I guess I croaked a guy tonight”
On February 3 1918, after a vicious gun battle that left two policemen dead,   George Raymond was killed by police after a tip led them to the gangs hide out on 4140 West Monroe Street. There the police found the black leather bag taken from Tierney at the depot. Arrested on the spot were Raymond friend and partner in crime George “Bugs” Moran and Emerson.
Emerson was eventually tried and convicted and was sentenced to thirty years in prison. While he was in custody, and already facing a long sentence in Minnesota, Emerson probably tried to cut a deal and started naming names and one of the names he gave was George Raymond but then he found out that Raymond dead and the cops wanted Tommy O’Connor.
So Emerson pointed the finger at Tommy O’Connor of killing Tierney at the depot. Emerson told a good tale, he said that prior to robbing the ticket office, he had warned O’Connor not to bring a weapon on the job which took place on February 1, 1918. Dennis E. Tierney, an ex-policeman and the collector of the daily ticket sales funds, was jumped and beaten to the ground by Hanraty, the Emerson gangs muscle. Hanraty took Tierney’s cash satchel that contained $2,500 in small bills. (Another figure was $1,500.00)
The gang ran for it but Tierney, badly beaten and bleeding staggered to his feet and chased them. Then, according to Emerson, O’Connor turned d and shot Tierney once in the chest, killing him.
“What did you do that for?” Emerson asked O’Connor.
“Because I felt like” O’Connor was said to have replied and then stuck the pistol in Emerson’s ribs and said “If you don’t like it, I’ll give the same to you” Emerson later told the police that he believed that O’Connor had panicked. Emerson was the only person to accuse O’Connor of firing the fatal shot.
On November 12, 1918, O’Connor was arrested on robbery charges and promptly offered to cut a deal with the police. He said he would finger Harry Emerson as the cop killer but the States Attorney turned down Tommy’s offer. They already Emerson pointing the finger at O’Connor and O’Connor was a much larger catch than Emerson and they told O’Connor as much.  At that point O’Connor might have thought that Emerson had to die before he went to trial.
Supposedly, and there are many versions of the story, O’Connor wanted Emerson dead and asked Jimmy Cherin to visit Joliet Prison where Emerson was being held and stab him to death with a knife claiming self-defense. The second most popular version of the story is that O’Connor told Chjerin to take $200 in cash to Moran as a down payment for the assassination of Harry Emerson.  Moran was jailed with Emerson. Chjerin, his father says, refused the offer, telling O’Connor that he had promised his father he would go straight so O’Connor killed him. Or so his father, another common criminal.
Cherin, “The Peacock of the underworld,” and the “The bad boy of the west side”) was a very far cry from weakling who could be pushed around by O’Connor. In fact, considering Cherin’s willingness to use his sizable brawn and fists in any circumstance and O’Connor weak knees and small stature, it was probably the other way around. Cherin had already had a very long criminal record that included a stint at Bidwell Prison.
Unlike O’Connor Cherin was a veteran criminal who was widely hated in the underworld because of his habit of agreeing to one percentage of the take from a burglary and then demanding a larger share after the job was done.  If the other half refused, Cherin clubbed them and in some cases, shot them.
Cherin’s first arrest came in 1911 when he was 13 years. On December18, 1912 when Cherin was 15 years old he was identified by over fifteen  witnesses as the kid who held up a cigar store at  2002 West 12rh Street at gun point and escaped with $1,500. Cherin’s intended victim seems to have been a big time gambler named Jacob Goldman. Apparently Cherin, who lived with his father at 1121 South Lincoln Street, (Cherin’s father’s saloon was on the first floor) who followed Goldman into the cigar store, decided to rob the store as well. The papers reported that Cherin’s father was “Indignant” at the cop’s assertion that his son was a stick up artist. In all, Cherin did at least one term in the Bidwell prison (For sticking up 25 men at one time) and racked up another twenty arrest overall.
Jimmy Cherin’s other partner in crime was a teenage hood named Jimmy “Bozo” Shupe (Born 1894) who lived 1526 West 13th Street. A week before Cherin was killed he had Shupe were arrest for driving around town in a stolen car.  (Cherin preferred to steal Ford’s because their street value was higher than other cars)
Shupe’s Brother Tommy, of 1608 West Madison Street, a partner of Fur Sammon and Three Fingers Jack White, later received a parole from Governor Len Small. Shupe was released to the care of State Senator George Van Lent who promised the Governor he would employ Shupe as “Political worker”. Jimmy and Tommy Shupe were believed to have murdered John Lafferty, a police informant.  A few months after his parole, Tommy Shupe robbed the International Harvester Company payroll. He was sentenced to 15 to 20 years in prison.
In 1926, Jimmy Shupe was a full-fledged member of the Capone operation and was caught up in small scandal when it was revealed that he, Three Fingers Jack White and Fur Sammon, while in the county jail lived like kings and held regular drinking session with booze brought in by the guards.
In May of 1929, the machine guns used in the St. Valentine’s Day Massacre were traced to Jimmy Shupe, who had received some of the weapons. By then Shupe was working with Machine Gun Jack McGurn. 
Later that year, on July 31st, Shupe was shot to death in an early morning gun battle near West Madison Street at Aberdeen. He died of his wounds at the Bridewell Hospital. At least three others were wounded in the shootout including Tommy “Big Six”McNichols, who, like Jimmy Cherin, was the son of a bailiff. His father was also a former state representastive.  By then Shupe had a twenty year arrest record ranging from petty theft to murder.
One version of the event sbehind the shooting said that McNichols ran a handbook and had moved in on Shupe’s gambling territory. Another version was that McNichols had fallen in love with Shupe’s live in girlfriend Corrinne Gillespie (Who had also lived with James LaPorte who would later escape from prison with Tommy O’Connor) and decided to girl Shupe to get him out of the way.
From what police were able to reconstruct, Tommy McNichols stepped from a car, weapon in hand and fired at least five shots at Shupe who stepped out of his car to return fire. Both men shot each other in the stomach and both died within an hour of each other. A man named George Riggin’s, who owned the cigar store where the shooting occurred, stepped out on the street and also fired at Shupe but was cut down with a shot through the chest. Remarkably he lived. But he killed on October 14, 1929, shot in the face none times as he entered the Jefferson Park Hotel.
The tall blonde who was sitting in Shupe’s car and drove him to the hospital, Corrinne Gillespie (She left the body at the hospital before police arrived telling the nurse “I’m going to get his mother”)
Gillespie had been married to a low level thug named Johnny Lafferty, who grew up with Shupe, Cherin and O’Connor. Gillespie and Lafferty had one child but soon she took up with Shupe and with her child, left lafferty to live with Shupe. Lafferty starting making threats about turning the Shupe Brother’s for their role in the mail robberies. The day after he went to the police with his story, he was murdered as he slept and stashed in the basement of an apartment house on the west side. When the cops told Gillespie what had happened she said “What’s that to me?”
On May 30, 1924, Shupe’s Brother Tommy was released from Joliet Prison on a highly dubious pardon by the very corrupt Governor Len Small. Unfortunately for Shupe, federal marshals were waiting at the gates. When Shupe stepped into freedom, the marshals cuffed him and charged him with having a role in the $1,500,000 Union Mail Station robbery on January 18, 1921. Shupe was on parole at the time of the robbery. His brother Jimmy was suspected of being the other gunman in the robbery that made off with a thousands of negotiable corporate bonds.
 Police surrounded the Shupe Brother’s at 1522 West 13th Street, where Jimmy Shupe lived (Tommy O’Connor grew up several houses away)  but the brother’s shot their way out of the apartment, overpowered a passing motorist, stole his car and escaped. Jimmy Shupe was arrested two days later on the corner of Pauline and Madison and in 1921 Tommy, carrying two pistols, was arrested at an apartment on 1448 West Harrison. Tossed into the Bidwell jail he promptly slashed his wrists and was committed to a mental asylum to recover.
Unlike the Shupe’s and his other doomed friends, Jimmy Cherin 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 part time crook and local political figure who was willing to pay off to keep his out of jail. 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. He blamed all of his son’s deadly habits on the neighborhood he raised him in. 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 and married her.

Gamblers war?

Jimmy Cherin was a punk with an attitude problem who had many, many enemies. He was also involved in a myriad of criminal enterprises including car theft, armed robbery, and gambling. He was also widely hated in the underworld for extorting other criminals. In a “pay up or pay” scheme, Cherin would either forcefully cut himself in for a percentage of a burglars take or threaten to use his father's  influence in the courts to have the crook arrested. There were a lot of reason that a lot people wanted Jimmy Cherin dead and on January 21, 1919, Cherin’s body was found in the back seat of a stolen Model T car on 79th Street and State Road in the town Stickney. (Today the area is mostly strip malls) he had been shot three times under the left ear; a pistol in his right hand was unfired. The corpse was identified Detective Charlie McShane of the Auto Detail.
The original source of the story that O’Connor killed Cherin’s came from Cherin’s father but it appears that his son may have been killed in a gamblers war that ripped the west side that year. The turf war was between the Stillwell Mob and the Jimmy Cherin Gang.
On January 16, 1919, Peter Badorf, a dice game operator, was shot and killed by his competitors, two well-dressed men wearing fur collar coats, as he left his dice game at Fifty-First and Wentworth Avenue. The men found Badorf on the street, pulled him into a waiting car and killed him and then tossed him out on the street. That same day freight thief Tony Dubrouse (AKA Tony Renni AKA The Tamale Kid AKA Rex) was shot none times and tossed from a speeding car at Ninetieth and South State Street.
Two days later Charlie Stillwell AKA Spider Man, (Stillwell, from Minnesota, ran a gang called “The West Sides Thieves Trust”) was killed in Alderman Barney Grogan’s 18th Ward Democratic Club (It was little more than a saloon) on West Madison.  Grogan, being Grogan, denied he knew who the legendary Stillwell was. Jimmy Cherin was killed in much the same way that Badorf and Dubrouse were murdered that same week.
The accepted story was that Jimmy Cherin’s 2o year old wife, Adelaide, had killed herself and her three year old daughter on June 4, 1919. Their bodies were found in bed at their apartment at 1121 South Lincoln Street. One newspaper story stated that she held a newspaper clipping about Cherin in her hand, but this seems to be a Romanized plant. Cherin’s father said that she had been having problems with the gas being turned doff for non-payment and that the death was accidental. But the version of the story that sold more papers was the one that essentially blamed the murderous Tommy O’Connor for driving a child bride to kill herself.


On November 13 1919 O’Connor was arrested…without incident…. for the murder of Dennis Tierney at the train depot, at his father’s home at 3329 West 16th Street. When police arrived O’Connor was in bed fast asleep. The state had a rock solid case and it all rested on Harry Emerson’s testimony.
Four days later, on November 17, 1920 Harry Emerson, who had already escaped from the Minnesota state Prison, escaped from Manard State Prison in southern Illinois while being transported from Chicago. Without Emerson, the state had no case against O’Connor and so on April 9, 1920 O’Connor was acquitted of the murder of Dennis Tierney.  Aside from a missing key wittiness, somehow, O’Connor’s defense managed to produce three witness who swore O’Connor was with them in Houston Texas on the day of the shooting. As soon as O’Connor was acquitted he was indicted for his role in the depot robbery.

The Louie Miller angle

Using his own criminal connections, Jimmy Cherin’s father had Louie J. Miller kidnapped from a Montrose Avenue saloon and brought to police headquarters where he was booked for the murder of Jimmy Cherin and where, after a beating, he swore that he had seen Tommy O’Connor gun down Jimmy the Peacock.
In his first statement, Miller, a Valley hood, told the same story about the Cherin killing that Cherin’s father had been telling people. He said he was sitting in the front seat of the car. 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.  Detectives picked up Tommy O’Connor and booked him for murder based on Miller’s statements.
In his second statement, Miller said that he stepped out of the stolen car they were in because the radiator had overheated and he walked to a nearby saloon to get water for the engine.  When he came back, Cherin was dead in the back seat.
On September 9, 1920, the day before the Cherin murder case was to begin Louis Miller was “kidnapped” at gun point from a saloon at 2335 Montrose Boulevard. (The saloon has changed names but the building is still there and remains a bar)  Miller later that said he was driven to a hotel in Madison Wisconsin and kept there for two weeks watched over by two guards at all times. He said “They gave me two hundred and warned me not to go back to Chicago and sequel and told me to beat it to California”
On January 8, 1921, acting on a tip from a Chicago Tribune reporter, the police grabbed Miller at his sister’s home in Rogers Park. The tip may have come from the Tribune but it was Cherin’s father who led police to Miller’s hideout in Rogers Park. “I got me a witness to prove he killed my boy and I’ll see that he suffers too” Cherin father said
 Miller 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. Miller was told that he could testify against O’Connor or face charges of stealing the car Cherin was killed in and accessory to murder. It was also agreed that the police would not pursue charges in December 1911 meat store robbery on Lawrence Avenue, at gun point, where Miller got away with $50.00
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. That same day Jimmy Cherin’s father Dominick and another man, John Witt, were indicted for stealing a car and selling it. The charges were later dropped.

The murder of Officer Patrick O’Neill

A series of unfortunate circumstances led to belief that Tommy O’Connor gunned down a Chicago policeman in cold blood. However a closer look at that story leaves questions. For one thing, O’Connor had no reason to draw on the police. He wasn’t wanted for anything that he knew of.  It’s not even certain O’Connor was armed when the police arrived at his sister’s home to arrest him. There is also a very good case that can be made to show that police accidently gunned down the patrolman in question.
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, married to O’Connor’s sister Mary, at 6415 South Washtenaw Avenue. The first official version was that five police detectives circled the house and O’Neill called inside for Tommy to surrender. According to the police, O’Connor burst through the door, guns blazing and yelled “Well, I’ll get one of you anyway! “and then fired five shots.
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. At that second, the police drew their weapons and fired. Offcier O’Neill fell dead. 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 Condon who drove O’Connor to Stickney where one of his men ran a saloon. There he was provided with clothes and food.
Exactly what happened on that back porch will never be known. The cop’s version of O’Connor bursting through the door shooting seems highly dramatic and very, much out of character for O’Connor who was, to put it simply, something of a coward when it came to a fair fight.  All agreed that the cops and the O’Connor were less than 15 feet away from each other and that the cops were grouped closely together, yet only one bullet of the five O’Connor was said to have fired struck anyone.
It appears that what actually happened was that O’Neill led three detectives up to the front door, their pistols drawn, a fourth detective circled around the front of the house. O’Connor walked out on to the porch and asked them what they wanted and that when the shooting started.
 On March 28, 1921 at 3 in the morning, a squad of heavily armed police, acting on a tip, surrounded a house on Belmont Avenue hoping to capture Tommy O’Connor who was said to be sleeping inside the property. He wasn’t there but minutes later there was a call that O’Connor was sitting in a car on Halstead and the squad rushed, again finding no sign of O’Connor.
At the same time the five cops who were suspended from the force for cowardice during the bungled O’Connor arrest.  At a police inquest into the conduct of the officers involved in the bungled attempt to arrest O’Connor and the death of Officer O’Neill, the officer s involved pointed fingers of blame at each other and contradicted each other statements “It was” said one of the hearing judges “The worst case of dog eat dog I have ever seen” Among the press, the rumors were that it was, as O’Connor said, one of the officers, probably Ronan, who panicked and killed Officer O’Neill.
In his formal report the chief of police wrote that after O’Neill was shot, the officer watched from a distance of cover as O’Neill cried out for help, struggled to his feet and collapsed. Fifty witnesses agreed with the chief summary that the policemen stayed in hiding while O’Neill cried (To officer Ronan) “Joe! Joe! Dear God help me”. But the cops stayed in hiding until the ambulance arrived and remained under cover until the ambulance attendants placed O’Neill in the Ambulance. He died 25 minutes later in the hospital.      
A week later, on April 4, 1921, the police received a tip that a drunken Tommy O’Connor was at the Crystal Palace Dance Hall dressed as a woman. The police raided the bar and searched everyone, including the dancers, but O’Connor wasn’t found. In the meantime a stick up artist named George Bolan was robbing people on the street, telling his victims that he was Terrible Tommy O’Connor.
A week after that on April 11 1921, five car loads of heavily armed police raided a cottage at 3347 16th Street, down the road from O’Connor’s father house, on a tip that Tommy was hiding there. In the house was O’Connor’s cousin, Jeannie O’Connor and her daughter Mary. When police kicked in the door, Jeanie O’Connor flung herself at the lead cop and landed several hard punches on his head before she was restrained. Again, Tommy O’Connor wasn’t there. 
On June 22, 1921, three police detectives were working a tip that Tommy O’Connor was seen several times in the valley neighborhood around 14th and Hastings Streets. The cops waited on 13th and Robey Streets when a car without a license plate drove past. The police put on the siren but the car without the plate came to a standstill and let out a volley of bullets and sped away. Earlier in the month he was said to have been seen in Indiana.

Captured in Minneapolis

By July of 1921, O’Connor had made his way to Minneapolis and brought a train ticket to Omaha. He had been drinking heavily. He yelled for a porter to bring another beer and when it was served O’Connor pulled out a pistol and told the porter to be quite and ran to the back of the car shouting for the porter to stop the train.
When the train stopped O’Connor leaped from the car and tried to board an engine car but the fireman, WL Woods, on the car knocked O’Connor on to his rear end with one mighty swing of his shovel. O’Connor stood, bleeding and tried to board another train but was overpowered by the fireman and an engineer who relieved him of his two pistols, a .32 in his hip pocket and .45 carried in a specially designed vest pocket along with six clips of bullets. He was also carrying a rosary, a scapular and a prayer card to St. Patrick.
Reports had Woods chasing O’Connor three blocks but police reports contradict that story.  It appears O’Connor was so drunk he couldn’t run and was easily overpowered by the two men.
In O’Connor’s view of events he said that “I got drunk and fell into a quarrel with a porter and fell off the train. The police furnished the three guns. I never had them on me, I would weight a ton if I did”
It was the Minneapolis newspapers that named O’Connor “Terrible Tommy” causing O’Connor to complain “What right did the Minneapolis newspaper have to call that? I’ve been made more notorious than Jessie James”
On July 30 1921, 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 Chicago Chief of Detectives Hughes with kidnapping. He sent three carloads of his detectives to bring O’Connor back but they were turned away at the city border.
Hughes (Who would always refer to O’Connor as “The rat”) explained that he didn’t have time to gather the correct extradition papers since he had heard in the underworld that burglar Tommy Touhy was planning to shoot O’Connor’s way to freedom. Tommy Touhy would eventually pick up Tommy O’Connor’s nick name “Terrible Tommy” except in Tommy Touhy’s case the name was actually true.  The underworld has seldom seen the likes of hood like Tommy Touhy, founder of the Touhy gang. 
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.”
“But” a reporter asked “You admitted to killing Tierney”
“No” O’Connor answered “What I said was that “They had me right in that case” but you newspaper boys wanted me guilty so you understood that I said “They had me right” and while we’re on it, I did not kill my good and dear friend Jimmy Cherin”
Later O’Connor asked Hughes “You won’t murder me if you take me back will you?”
“No’ Hughes answered “We’re just going to hang you that’s all”


In Chicago O’Connor would be represented by lawyer, WW O’Brien whose law partner was William Scott Stewart, defense attorney to the underworld. The firm’s clients included Roger and Tommy Touhy, most of the North Side gang including Hymie Weiss. Both Stewart and O’Brien were models for a composite character Billy Flynn in the stage play and film Chicago.
On August 1, 1921, speaking from his jail cell a smiling and optimistic Tommy O’Connor told reporters that he was worried about his upcoming trial since was innocent and held to his claim that the police themselves accidentally shot officer O’Neill. “I’ve had so much publicity since that O’Neill affair I’d have no trouble getting a job as a screen star” he told the press “(In Minneapolis) everybody including the mayor came by to shake my hand. The girls were very nice too.”  
Five days later, on August 6 1921 Officer James Rafferty of Highland Park identified O’Connor as the man who shot him on the night of April 10 1921. That Raffery had been  ordered to stop and question all suspicious cars. He stopped a Packard on the corner of St. John’s and Central Avenue. Someone was huddled in the back seat and Rafferty shown his flash light on the person and asked “Who are you?” and the man sprang forward and shot the cop in the chest and the car sped away. Rafferty claimed he knew O’Connor and could identify him as his shooter. The entire Rafferty issue was very suspicious. He refused to press charges against O’Connor and then disappeared for several weeks and had to be brought into jail house by Chicago police to identify O’Connor.
The most damaging testimony came on September 21, 1921 when Tommy’s first cousin, Mary Millane, and her husband Cornelius and her 10-year old daughter testified that O’Connor came to their house at 1726 Wellington Avenue on the day of the O’Neill killing and told them that he had been in a shooting with police and left a while later armed with two pistols. 
Four days later on September 25 1921 O’Connor was found guilty and sentenced to hang. The jury was out for three hours and took two ballots to decide Tommy’s fate. The second ballot, nine to three, fixed the death penalty on O’Connor. The verdict was read at 2:12 in the afternoon. When it was read O’Connor’s father, David, rose to his feet in shock. “It’s the wronest verdict in the world” he said later “We couldn’t get no justice for our boy. No 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.
O’Connor was scheduled to hang for the O’Neill murder on December 15.  On December 8 1921, the state Supreme Court refused to hear his case and all the while O’Connor repeated his story that the police shot O’Neill and not him.

The Great Escape

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 out-side 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, spent his idle hours with Darling Dave O’Connor at a saloon on Hoyne and Madison Streets in the Valley neighborhood where they were raised. (A library sits there today) boasted openly about providing the two guns for Tommy O’Connor’s fabulous escape from prison. Touhy 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 that were intended for another prisoner, but the jail’s cook, William Fogarty, a convict himself, gave (or more likely sold) 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 when  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.
In this illustration that ran in the Chicago Tribune on Dec. 12, 1921, jail guard David Strauss was grabbed around his neck, choked, and held to the bars by James La Porte, Tommy O'Connor's cellmate. O'Connor held the gun, a nickel plated revolver. After his keys were taken, Strauss was bound and gagged and thrown into a cell. The jail break occurred on Dec. 11, 1921.
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.
In this illustration that ran in the Chicago Tribune on Dec. 12, 1921, Tommy O'Connor holds other inmates at bay with a nickel-plated revolver while his confederates throw jail guard David Strauss in to O'Connor's cell on the fourth floor. Tommy O'Connor escaped from jail on Dec. 11, 1921.
In this illustration that ran in the Chicago Tribune on Dec. 12, 1921, Tommy O'Connor and four of his buddies emerge from the cellar and run across the jail yard to scale a 20 foot wall to freedom. The old county jail was located at Dearborn and Illinois Streets. Tommy O'Connor escaped from jail on Dec. 11, 1921.
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.”
“O’Connor did not escape” said Chicago’s Chief of Police FitzMorris “He was let out”

The man Hunt

On the day he escaped from jail, O’Connor (or someone who looked like him) was spotted near the town of Richmond Ill. And O’Connor’s cousin Jack O’Connor reported that someone had broken in his cottage near Fox Lake, spent the night, stooled nothing and left.
Then there was a report of O’Connor being spotted in Hartford, Wisconsin on December 14 1921, when a detective was almost killed when the squad car he was riding in with five other Chicago Detectives skidded out of control, flew off the road and flipped over. Four other detectives were injured. The cops were on their way to Hartford Wisconsin where local police said they were holding Tommy O’Connor whom they had arrested in the Kasper hotel. Reporters from the Chicago Tribune made it to the city before the police and realized the man being held was not O’Connor but teenager who was travelling across the country with a high school friend.   
On December 17, 1921, the body of a man was found under a bridge three miles north of Palmyra, Wisconsin in rural Jefferson County, about 16 miles north of the town of Elkhorn.  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.
That same day, O’Connor was seen driving out of Chicago with Bernie Grogan, the powerful boss of the 18th Democratic ward. (Later the 20th Ward)  The two were later spotted in the same car in Jefferson County where the body was found.
Grogan “The West Side Boss” who came to power in 1911. He essentially ruled over the area where O’Connor lived and operated out of an unlicensed saloon at 1160 Van Buren Street (It’s a shell gas station today) which was firebombed in 1923.
Grogan was said to have driven O’Connor to his farm near Kosh Konong Wisconsin and Grogan’s housekeeper, Etta Barry, later identified the dead man as a guest at the farm with O’Connor. Remarkably absolutely nothing happened with this information.
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.”
On June 21 1921 Big Tim Murphy, a labor racketeer who controlled several major railroad, laundry and dye workers' unions during the 1910s and early 1920s was arrested for his part in a $380,000 mail robbery and, it was learned through wire phone taps, he was planning a second heist with Tommy O’Connor later in the year. A police informant, Murphy was paying $125 a month for a 3rd floor apartment for O’Connor and his girlfriend on Sheridan Road near Irving Park Blvd.
When police learned that, they tapped the house phone lines and put the entire block under a twenty four hour watch, hoping to catch O’Connor out in the open and rented an apartment across the street from the place he was supposed to be staying.  They learned that apartment had been rented in the name of Abe Meyers, Attorney. Actually the person calling himself Meyers was Abe Schaffner, part of the original Emerson gang that robbed the depot. After a week, police raided the apartment only to find O’Connor long gone.  Murphy was eventually convicted and sentenced to seven years in prison for the robbery. On June 26, 1928, Murphy was shot and killed as he answered the front door of his home.
On December 19 1921 another note arrived for Harold R Wakeham a wealthy owner of a fruit packing company. He had place a public reward of $100 to anyone who would lead the police to Tommy O’Connor. On that same day, someone placed a hand delivered note in Wakeham’s mail box telling him that if he didn’t withdraw the offer he would be killed.  Although Police suspected a local crank of writing the note Wakeham was given round the clock police guards anyway.
A day later, December 20, 1921, police in Louisville Kentucky identified a man who had leaped to his death from a bridge into the Ohio River as Tommy O’Connor. A detective from Chicago later disregarded the claim because the corpse had a long jagged and very old scar on its right hand which O’Connor did not have.
On January 3 1922, Alec Portman, a train brakeman, identified Tommy O’Connor as the man who bordered the engine car of a train and tried to rob it near Horwden Iowa. Portman struggled with the gunman and tossed him from the train and the robber fled.  That same week, on January 11 1922 Abraham Schaffner, the crook who took part in the depot robbery, was arrested for the daylight robbery of a Chicago bank manager.
Two months later on March 18, 1922 Iowa police suspected that O’Connor was behind a rash of bank and postal robberies across the state and the US Secret Service confirmed that O’Connor was linked to the robberies as well and that was the last that was ever heard of it. A few months later, acting on a tip that O’Connor was working as a cook in a railroad camp near Carkinville Ill., raided the camp and arrested a man named Sullivan, whom, they assured the Chicago Police, was O’Connor. It wasn’t.
On April 18, 1922 Detroit police arrested John Kelly, another O’Connor look alike. Chief of Detectives Hughes drove to Detroit only to discover that the cops had arrested the wrong man.
In May, a man named John Drexel walked into the LA Police headquarters and said that he had been one of Tommy O’Connor’s get away drivers after bis escape from prison (He said O’Connor used several get away car). He was held, determined to be insane, and released.
On July 4 of 1922, a woman called the Chicago police and said that O’Connor was having a drink at Hallstead and North Avenue. (It’s a jewelry store today) Police rushed to the site but O’Connor wasn’t there.
In early December of 1922 Tommy O’Connor was reported to have been seen in Detroit and Gary Indiana, in an apartment at 518 Washington Avenue, rented by a man named John Rees (The house is long gone, replaced by a parking garage) where Chicago detectives, led by Detective John Ronan, raided an apartment, and according to them, they missed O’Connor by only moments.
On December 10, 1922, O’Connor was reported to be in the town of Elkhorn, Wisconsin where, eleven years later, Roger and his gang ran into a telephone poll. A local policeman searched their car, found a small armory and phoned the FBI who promptly arrested Touhy and company for the kidnapping of St. Paul brewer William Hamm.
A year later on September 21 1923, a man was held in Carlinville Ill. on suspicion of being Tommy O’Connor but was released and two months after that, on November 22 1923 O’Connor was said to have been spotted in Texas by a man who said he recognized O’Connor from his photo in detective magazines.
In 1924, a man named Mays found out that the man his daughter married was not named Ryan as he had said, but O’Connor.  Ryan said he changed the name because he too was originally from Chicago and knew that he bore a striking resemblance to Terrible O’Connor so he changed his name to Ryan.  Further, Ryan said he knew O’Connor and was a friend of his and had visited him at the jail three days before his escape. Even more incriminating, the man had recently sold an unregistered revolver at a pawnshop.
The most interesting claim came on January 29, 1927, when two Chicago hood drove to Detroit and started a robbery campaign.  The police found them as they were staging the last of seventeen robberies that day. Six members of the Chicago police gunned it out with the pair. One policeman was killed and another seriously wounded.
The shootout took place in front of the Garden Court Apartments on East Jefferson Street.  The two gunmen entered the drug store and demanded every present to lie down on the floor, however one person, the store clerk crawled out of the store through the back and phoned police. Officer Stacy Mizner and Officer Edward Gerring walked into the store and said to one of the robbers “I understand there has been a stick up here”
“Yes, there has” one of the robber’s responded “Come back this way”
Officer Gerring stepped forward and the robber stuck a gun in his ribs but Gerring grabbed the gun and as the two men struggled, the second robber shot Gerring in the back.  Officer Mizner opened fire and the two gunmen returned fire hitting Mizner three times and killing him instantly. The robbers fled out the back door but another policeman was waiting for them and fired three shots into Dale.
 The second gunman listed only as “Scotty” in the newspaper accounts, (Probably Chicago gunman Ray O’Neil) ran across the street shooting but was gunned down by three other cops who had just arrived on the scene. They shot him 30 times.
One of the bandits, a Chicagoan named Martin Dale, a rapist, car thief and burglar, said as his dying words that  the robberies had “been framed for us a cinch by Tommy O’Connor” and then he died. It was known that they had visited a prison in Jackson Michigan and it was assumed by some members of the Chicago Police that O’Connor was an inmate there.  There was a theory that O’Connor changed his name, moved to Kansas, allowed himself  to be arrested for bank robbery, admitted to the crime and spent five years in prison, long enough for the heat to die down. When he left prison, he left with a new although sullied name and a background.
April 18, 1922 Detroit police arrested John Kelly, another O’Connor look alike. Chief of Detectives Hughes drove to Detroit only to discover that the cops had arrested the wrong man. July 4, a woman called the Chicago police and said that O’Connor was having a drink at Hallstead and North Avenue. (It’s a jewelry store today) Police rushed to the site but O’Connor wasn’t there.
In December of 1922 he was reported to have been seen in again Detroit and Gary Indiana, in an apartment at 518 Washington Avenue, rented by a man named John Rees (The house is long gone, replaced by a parking garage) where Chicago detectives, led by Detective John Ronan, raided an apartment, and according to them, they missed O’Connor by only moments. It should be noted that all of the detectives who were involved in the shooting where Officer O’Neill was killed, were suspended by the chief of police who said he would hold them under suspension until O’Connor was O’Connor.  They arrested three persons, John Fieldhouse, James Stanley and Bessie McAvoy, known as Black Bess who was said to be O’Connor’s girlfriend of many years.
McAvoy arrived in Detroit from Halifax, Canada (Her mother still lived there) in 1915 when she was 22 years old and listed her occupation as “Chocolate Baker”. For many years, members of the Chicago police force assumed O’Connor had hidden in St. Paul’s large underworld and then slipped over the Canadian border before traveling to Ireland. On April 11, 1922 the Niagara Falls Police called the Chicago police and told them they were holding a man who looked exactly like Tommy O’Connor. The man provided them with a name, Edward Beeber, but refused to give them an address. However he was released after twenty four hours when no proof that he was O’Connor could be provided.
In 1923 Carlinvilee Ill., acting on a tip that Tommy O’Connor was working as a cook in a railroad camp, raided the camp and arrested a man named Sullivan, whom, they assured the Chicago Police, was O’Connor. It wasn’t.
In 1924, a man named Mays found out that the man his daughter married was not named Ryan as he had said, but O’Connor.  Ryan said he changed the name because he too was originally from Chicago and knew that he bore a striking resemblance to Terrible O’Connor so he changed his name to Ryan.  Further, Ryan said he knew O’Connor and was a friend of his and had visited him at the jail three days before his escape. Even more incriminating, the man had recently sold an unregistered revolver at a pawnshop.  At the same time, Los Angeles police were certain (based on underworld rumors) that O’Connor was hiding out in the city someplace
In 1928 Dominick Cherin, Jimmy Cherin’s father, was a clerk in the election office (A step up from his first city hall position as bailiff) and was called in for questioning in the Boss Eller conspiracy case. Cherin the elder died in March of 1943. A year later in 1929, Barney Grogan died of a stroke at age 68. He had long since been ousted from power by John J. Touhy
The search for O’Connor went on although now mostly as a curiosity more than anything else. In 1930 a newspaper editor in Chicago let it be known in the underworld that he would pay very big money for an interview with O’Connor but that went no place. A year later, in 1931 O’Connor was said to be spotted in Mineola, Texas, but that turned out to be another false alarm. In 1933 he was reported in the press to be running Roger Touhy’s kidnapping squad. In 1959 Tribune reporter John Gavin also reported that O’Connor was working with Roger Touhy.  It is likely that the Touhy’s hired at O’Connor, at least for a short while.  Most of the heavies in the Touhy gang…the gunmen and mail robbers……were escaped convicts or were on the run from the law, including Touhy’s top lieutenant Basil Hugh Banghart.  Another report had O’Connor fleeing to the North woods of Minnesota and settling down.
In 1937 rumors began to circulate that Tommy O’Connor had died of tuberculosis, a disease he had contacted as a child in Chicago but the most oft repeated story among those who knew him was that O’Connor had escaped to Canada and then back to Ireland where he ran bar until his dying day. He certainly knew a thing or two about running a bar since he all but lived at Cherin’s saloon in Chicago and his father, Joseph, left a number of siblings back in Ballykenny that included his brothers James and Gerald and sisters Bridget, Elizabeth and Mary.
It was also rumored that Terrible Tommy O’Connor died in 1951. The source of that rumor is gravestone in the Holy Sepulchre Cemetery, Cook County Ill.  Under the tombstone lays one Thomas O’Connor who died on January 31, 1951. Buried next to him is his wife, Annie Connor (nee Fitzgerald) who passed away on February 16, 1956.
Thomas and Irish born Annie were both waked at funeral home at 1136 West 87th Street, Chicago but the management has changed several times since then and the funeral director has no record of the burial.   A service was held for both of them at St. Killian’s Church 3200 East 91st Street in Chicago.
The cemetery lists Thomas O’Connor’s date of birth as March 10 1880 in Ireland in the village of Kilcolman, Limerick which is 15.4 Km (about a 20 minute car ride) from Tommy O’Connor’s birth place in Monagea, Limerick. However, several times the US census listed Citizen Thomas O’Connor birth year as 1881. Terrible Tommy O’Connor was born ten years later in 1891.   On another census Citizen O’Connor listed his birth year 1883.
 Citizen O’Connor said he arrived in the US in 1905 and his wife in 1900 and that he worked as a municipal laborer. They lived for most of their lives 8843 South Halstead Street, Chicago, about ten minutes from the end of Polk and Damen where Terrible Tommy O’Connor was raised and lived until he disappeared.  The couple, who were married in 1919, is found at the same address in 1935. In the 1940 both were listed as 59 years old. Citizen O’Connor attended school up to the 5th grade.

The significant difference is that Citizen Thomas had a brother, Richard according to the Obit posted by the wife. However there are no census records listing Thomas O’Connor with a brother Richard in the US that matches the other data around citizen named Thomas O’Connor. It should be mentioned that a quick look at the US Census records show at least a half dozen Thomas O’Connor’s who could match almost all of the above date.
It is more than likely that the high strung, rash, O’Connor, who appears to have had a developing drinking problem and no skills, remained a criminal and was most likely killed in a caper gone wrong. 

Tommy O’Connor was the last person sentenced to die by hanging in Illinois. Due to lack of use the gallows were disassembled (actually the wood had rotted by the mid 1960s) but by law could not be destroyed and were stored as a big pile of wood in a basement for over 70 years in the unlikely event that O’Connor ever resurfaced. In 1977 Judge Richard J. Fitzgerald decided that O’Connor was gone forever and ordered the gallows to be disposed. The city of Chicago sold the gallows to Donley Wild West Town in Union, Illinois where they stayed for nearly 30 years.