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.