My father was a Chicago policeman. An honest one.
Otherwise, he would have had a hell of a lot less
trouble getting up the grocery and rent money. And I might
have managed to get farther in school than to squeak
through the eighth grade.
I was born in 1898, although the prison records say '97,
in a house at 822 South Robie Street, not far from one of
the places where I hid out while on the lam in 1942.
There were seven of us kids, two girls and five boys.
We lived in an area of working people, big families and
low incomes. My father's pay as a policeman wasn't enough
to keep the wolf off the front porch but, at least, he never
made it in to eat the potatoes and meat—when we had
meat, that is—off the table.
Some of Chicago's most notorious gangsters came out
of that part of the city. So did business leaders, college
professors, clergymen and a couple of mayors. I was doing
all right myself until the big Factor frameup came along.
My mother died when I was ten. She was fatally
burned when a kitchen stove exploded. After that, my
father, my two sisters and I moved to Downers Grove, a
suburb. The older boys stayed in Chicago, living with rela-
tives and friends. I graduated from the_£L._Joseph Roman
Catholic Parochial School i^TJowners Grove" when I was
It was a good enough boyhood. I played baseball and
raised the usual amount of the devil and got teased because
my hair was curly. If I had anything to gripe about, I
didn't realize it, because other boys didn't have any more
than I did, generally speaking.
I often thought in prison of the priest in charge of the
school, a Father Goodwin. My family couldn't afford to
pay tuition for me, so I was a sort of handyman around
the school and the church. I mowed the lawns, served mass
as an altar boy, tended the furnace, ran errands and did a
little janitor work. It was fun.
Once or twice a week, Father Goodwin rented a horse
and buggy from a livery and went calling on his parishion-
ers. I was his driver. At whatever house we stopped, there
would be refreshments—apple pies, lemonade, thick sand-
wiches, salads, pickles, ice cream. Father waved the food
away, but I ate fit to bust a gut.
In the church there was a big oil painting, a copy of The
Last Supper. Father Goodwin explained it to me, saying
that a man called Judas had betrayed Jesus Christ for
thirty pieces of silver. A thing like that can have a re-
markable influence on a kid.
I began thinking of Judas as a stool pigeon, a word I
knew, as did all youngsters. While sweeping up the church
and dusting the pews, I would stop and look for a long
time at the painting. I picked out the face of a man I
figured was Judas, and I would stand there hating him.
I thought of cutting the face of the man I concluded to
be Judas out of the picture, but that would have ruined
the painting and Father Goodwin would have been un-
happy. So I just went on despising Judas—something which
I never told the "bug doctors," which is what psychologists
and psychiatrists are called in prison.
My contempt for informers grew on me as the years
passed. When I later got into the labor union movement, I
despised the company finks. After a few years in prison, I
got to distrust everybody around me, except for a few
convicts. Too many inmates are stoolies; the bug doctors
can call my attitude antisocial if they want to.
My feeling about informers can be summed up by an
anecdote which seems very, very apt to me. Funny, too.
I once knew a confidence man called Yiddles Miller. He
spoke with a Weber and Fields Dutch accent, but he was
a shrewd operator. Con men are, I learned in prison, the
elite of all lawbreakers, in the opinion of other felons. They
never tattle on each other.
Well, Yiddles and another bunco expert, Gus London,
were sharing a twin-bed hotel room in Pittsburgh. Each
of them folded his pants across the back of the chair near
his single bed. E£ch fell asleep, but in the middle of the
night Yiddles, a light sleeper, was awakened by a prowler
in the room. London slept on, snoring a bit.
The thief took London's pants from a chair at the bed
nearest the door. He then moved toward the second chair.
Yiddles, feigning sleep, stirred and pretended to be awaken-
ing. The burglar left, taking only London's pants, with $3,-
000 in the pockets. Yiddles got out of bed, double-locked
the door, propped the back of a chair under the doorknob
for added security and went back to sleep.
In the morning London awakened, demanded to know
whether his pants had walked away with his $3,000, and
was told by Yiddles: "A burglar came in and stole your
trousers." London was indignant, demanding to know why
Yiddles hadn't awakened him, summoned the hotel house
officer, or called the police.
Yiddles propped himself up on an elbow, stared in as-
tonishment at his comrade in larceny and demanded:
"What do you think I am, a stool pigeon?"
London thought over the questionable ethics involved,
agreed that Yiddles was right, and apologized for having
suggested calling in the law.
Whatever the moral, or immoral, angles of the story
may be, I always have despised stoolies, and I always will.
The only thing worse is a perjurer. I have had more than
my share of troubles from both.
When I got out of the eighth grade, it was hunt-a-job
for me. Only rich kids went to high school back then, and
I didn't qualify. I had a little edge on other youngsters,
because my hobby was ham radio, or wireless as it was
called. I had built my own set at home, and I knew the
I tried for a job as a wireless operator, but there wasn't
a chance at my age. Too young for responsibility, I was
told. So I ran my feet down halfway to my ankles as an
office and stockroom boy for a few months and then hooked
on with Western Union. They made me manager of a little
residential section branch office. A real big dealer, I was.
Salary: $12 a week.
I lied about my age to get the job, but it was easy to get
by. My hair was gray at the sides of my head —maybe I
worried as an infant—before I got out of knee pants, and
every day I would have a five o'clock shadow by lunch time.
Western Union gave me a chance to learn the Morse code
which wasn't too difficult because I already knew the In-
ternational. They moved me to the main office downtown
and I was an operator.
My father went into retirement about that time, and he
liked to play the horses. He would bet fifty cents, or one
or two bucks on a race, and only one race a day, when he
had the cash to spare. And now I was in a position to be
his personal tout.
The stable owners, trainers and jockeys would send
messages on the chances of their horses over the wires. I
tipped off my father. He had nine winners, mostly long
shots, in a row. He would have broken half the bookies in
Chicago if he had started with ten bucks and parlayed it.
But no, he never risked more than two.
But the really important thing that happened to me—
back then in 1915—was that a dark-haired Irish girl
went to work for Western Union in the company's branch
office in Chicago's finest hotel, the Blackstone.
She was sixteen, and fresh out of telegraph school.
From the main office, I sent the Blackstone's messages to
her and received the ones she transmitted. She sent better
than she copied, but she wasn't so good at either. I tried
to help her.
Since she worked from four p.m. to midnight, I could
drop in and see her evenings after my day shift ended. The
first time I called only to help her with telegraphy. After
that I courted her by the Western Union's wires between
the main office and the Blackstone. And in person, too.
I'd take her home now and then when she finished work
at midnight, but she always had a chaperon. Another
pretty girl, Emily Ivins, was night telephone operator at the
hotel and she made certain that everything was proper on
those late-at-night-ride-home dates.
Miss Ivins, incidentally, was to be an important witness
in trying, many years later, to keep me out of prison on
the Jake the Barber hoax. She was to tell the truth, but it
wasn't good enough against the screen of lies behind
which Factor and his friends stood grinning.
I would have been a telegrapher for the rest of my life
but, odd as it sounds, I was too damn honest. The Com-
mercial Telegraphers Union of America was trying to or-
ganize Western Union and the Postal Telegraph Company.
I didn't know anything about unionization and I wasn't
interested, but I knew some of the operators in the office
Every hour, the operators got a ten-minute "short," or
relief, and we would go into the men's lounge for a smoke.
One of the CTU boys scattered organization pamphlets
around the room. I picked up one and, like a dummy, read
it right out in the open. A company fink saw me and
within an hour I was on the pad in the superintendent's
office. He had a lot of questions to ask.
Did I belong to ther union? No. Did I know any men who
did belong? Yes, I did. Would I give him their names?
No, I would not. Did I have any plans for joining the
union? "Well," I said, "if I decide the union is a good
thing, 1 probably will take out a card."
Whammo! I was fired and out on the street. A company
guard escorted me to the door and told me never to come
back. Now, I'm not rapping Western Union after all these
years. Every employer fought the unions then, and the
National Labor Relations Act was nearly 20 years in the
future as the bosses' nightmare. I would have been fired
anywhere for giving the same answers about unionization.
I should have lied to the superintendent, of course.
Honesty was my downfall. A CTU organizer came to visit
me at home that evening. He brought along an armful of
union literature and a paid-up card in the union for six
"You're all through as a telegrapher, Touhy," he said. "By
this time, your name is on the blackball list. No telegraph
company or brokerage office will hire you. But if you want
a job with us as a union organizer, we'll hire you."
I didn't believe him about the blackball, but he was
right. Nobody would accept an application from me, much
less give me a job. The hiring boss at the Associated Press
needed operators, but he turned pale and looked ready to
climb the wall when he heard my name. I could have been
a bearded bolshevik with a bomb under my coat.
I read the union literature and got impressed with the
rights of the working man. I took the job as an organizer,
which was a lot of hard work and a smattering of prankish
fun. We would call up Western Union and Postal, dictate
long telegrams to fake addresses in distant cities and send
them collect. We kept the companies' messenger services
jumping with requests to pick up telegrams from vacant
One of the union men telephoned the non-union Asso-
ciated Press, posed as the AP's reporter at Rockford,
Illinois, and turned in a long, fake story about a hotel fire
that had killed twenty people. The story would have got
on the wires, too, but some smartie called Rockford to
It wasn't too difficult to sign up telegraphers in the un-
ion. The working hours were long, the pay was skinflint
and the bosses were nasty. The trouble was that as soon
as a key-pounder signed a secret union application card he
was fired. I figured we had a stool pigeon in the CTU of-
fices and I suspected one of our office secretaries.
So we forged the names of ten Western Union finks to
application blanks and gave them to the secretary. Sure
enough, all ten of the informers were fired, including the
one who had squealed on me. We got rid of the girl we
suspected and things went better.
Unions didn't have big enough treasuries to hire meeting
halls, so we usually met in saloons. I got to know the big,
tough, two-fisted pioneers of unionism. There were Pete
Shaunnessey of the bricklayers, Tom Reynolds and Tom
Malloy of the movie projection operators, Steve Sumner of
the milk wagon drivers, Umbrella Mike Boyle of the elec-
tricians, Big Tim Lynch, Con Shea and Paddy Burrell of
the teamsters, Bill Rooney of the flat janitors, and Art
Wallace of the painters.
Those men were to figure, innocently, in my being rail-
roaded to prison. Their names will crop up later in this
story. Some of them were honest enough to get murdered
and others were so crooked they could sleep comfortably
only on a circular stairway.
Their faces were scar-tissued from fighting hired strike-
breakers on picket lines. Their skulls were permanently
creased from bumping their heads on the tops of police
paddywagon doorways. Their knuckles, sometimes, were
driven halfway up to their wrists from past impacts. I
admired their courage and I made lifelong friendships with
them—short as some of their lives were.
Con Shea was an erudite character who delighted in us-
ing fancy words. I recall his saying to me one night at the
bar at the Ansonia Saloon: "Roger, a divided or deviated
septum is an occupational hazard of the profession of un-
ion organization." I nodded wisely, not wanting to appear
dumb. When I got to a dictionary, I learned that he was
talking about a busted nose.
Union organizing was fascinating, but there didn't seem
to be a secure future in it. Anyway, I liked telegraphy. I
joined the Order of Railroad Telegraphers, went west and
wangled a job from the Denver & Rio Grande Railroad.
The pay was magnificent—$185 a month.
Everywhere the Denver & Rio Grande went, it seemed
to parallel streams alive with big, fighting mountain trout.
I learned about game fishing there. Also, I became
acquainted with ranching, horseback riding and financial
security. I worked in small towns where living costs were
low, and I sent half my pay home to help out the family.
I wrote long letters and sent small gifts to Clara, the
girl telegrapher back in Chicago who was going to be my
wife. I was sure of that even then, although I never had
proposed to her.
I worked in the depots, with their round-bellied wood-
burning stoves in Buena Vista, Glenwood Springs and
Eagle, Colorado. In Eagle, I got my first warning of
western bad-man danger when a local merchant told me:
"You won't be here long, sonny. We got a rancher, Clyde
Nottingham, who runs depot agents out of town. He carries
a gun. Guess he don't like you depot agent dudes."
It was cold that first night in Eagle and I had the stove
red hot as I jiggled the telegraph key, handling freight car,
stock car and personal messages. The waiting room door
opened and in came a big man in cowboy clothes and a
sheepskin coat. He spat on the potbellied stove. Sizzle, siz-
zle, the stove went.
I walked to the ticket window, looked out and saw the
caller was carrying a .45. He didn't look pleasant, but
damned if he was going to run me out of town. "Mr.
Nottingham?" I asked. He nodded and I said: "Mr. Not-
tingham, any time you want to spit on the stove, go right
ahead. But come back next day after the stove cools, and
polish it. I ain't going to do it."
He stared at me for a long time. My proposition was
reasonable to him, I guess. He came to my window,
reached into an inner pocket and handed me a half dozen
letters. He asked me if I would put them in- the slot of the
mail car on the late train.
I made another proposition: "I put your letters on the
train and you stop spitting on the stove? Right?"
"That's the idea, young fellow," he said. "Only reason
I been running depot agents out of town is they don't want
to mail my letters for me."
A fine friendship started right away. He invited me out
to his ranch. He had a ten-year-old daughter called
"Toots," and I always get along well with kids. The three
of us went fishing and hunting and horseback riding to-
Meeting Nottingham taught me a lot, as a young fellow
away from home. I learned from the incident in the depot
that the town bad man—or later, the rioting con in prison
—pretty often isn't bad at all. His trouble is that he can't
make himself understood to the depot agent, or the yard
screw, or to his family—and he gets sore at people as a
Being with Nottingham and his kid gave me a sense of
belonging, of being liked and being part of something.
Second to my own wife and sons, I thought a lot about the
Nottinghams at night in Stateville.
But nothing could be permanent back then. A war was
going on in Europe, and then the United States stepped in
and it was World War 1.
I got patriotic and headed back for Chicago to enlist in
the Navy. The Nottinghams saw me off at the station and I
tried to make Toots stop crying by promising to bring her
back half of Kaiser Bill's waxed mustache.
I didn't win the war, or have any active part in it, but the
war did something for me. It gave grounds for me, a boy
from the eighth grade, to say honestly to cops, bootleggers,
convicts, prison screws and interviewers: "I've been to Har-
vard." It was the truth, too. I taught telegraphy at Harvard
to classes of enlisted men and officers.
After my discharge from the Navy, I spent a couple of
weeks with my father, living in Franklin Park, a Chicago
suburb. I saw that cute little girl telegrapher a few times,
but I had a job of getting back on my financial feet be-
fore becoming serious about marriage.
I drifted out to a small Iowa town near Des Moines,
on a telegraphing job for the Rock Island Lines, then to
Kansas City, figuring I might go back to Colorado. But
I met one of my Morse code students from Harvard.
He was a bright young man, a lawyer, although I hadn't
been able to pound telegraphy into his head. He just didn't
have an ear for Morse signals. I'll call him Collins, for the
good reason that he had a different name.
Collins was heading for Cushing, Oklahoma, where his
brother had an interest in a hotel. The two brothers also
had a tire shop in Oklahoma, and I wound up as manager
of the store. There wasn't enough money in that job, but
it was a stopgap.
The oil business was boiling and busting and gushing
in Oklahoma. A guy could make a million overnight. That
was the line for me, particularly when I thought of my
little Irish telegrapher back in Chicago. Marriage was on
I didn't know any more about the oil business than a
mink knows of sex hygiene, but I could learn. For a bottle
of bootleg corn, I got an oil field engineer to give me a
couple of hours of instruction in engineering. Now, all I
can remember of what he taught me is: "Don't bump your
skull against an overhead valve and smash your goddam
I went to a field at Drummond, Oklahoma, told the
superintendent I was an engineer, and went to work. I
was short on technical skill, but long on bluff. And I
knew where to buy corn whiskey to give the mechanics
for doing my work when something went wrong with the
pumps or engines.
wildcat wells. Raymond would study those things, look over
the terrain and decide whether any of the land was worth
leasing from the owners, who were mostly Indians and cattle
I had about $1,000 saved, and there was nothing against
my buying leases that Raymond recommended. I took a
gamble on 150 acres at two dollars an acre in Jefferson
County. Three oil companies were bidding on my lease
within a month, and I made $2,000 on the deal. I bought
and sold about 20 leases, and never lost on any of them.
The money was good, but I was a guy who liked the
city. And my mind was on the girl at the telegraph key in
the Blackstone in Chicago. I went back home with $25,-
000 in cash, a fortune in 1920, and it had taken me less
than a year to earn it.
Clara and I were married on April 22nd, 1922. I had
figured on returning to the west, but Chicago looked too
good to me, and there was a lot of money around. Every-
body was buying cars and trucks and that was the busi-
ness for me.
A boyhood friend, John Powell, had an auto sales agen-
cy on Madison Street. He was a politician, and later he be-
came an Illinois state legislator and went blind. But at
that time he was a real rouser. Powell was a six-footer,
and he had a black bear that was just as tall when it stood
on its hind legs. When Powell went night clubbing, the
bear went along, and both of them would drink bourbon
with beer chasers. It was a race between them as to who got
I went to work for him (Powell, not the bear) as a car
and truck salesman, at no pay. My idea was to learn how
to buy and sell, and then go into business for myself.
My wife and I were living in an apartment in Oak Park,
a sedate suburb where every man was a municipal disgrace
if he wasn't a deacon, or at least a pillar of a church. To get
away from that mad social gaiety, and to keep my bank-
roll intact, I bought a taxicab and drove it nights in Chi-
cago. I learned things in the cab I never heard at Harvard.
In a few months, I opened my own garage and auto
sales place, with a capacity of 15 cars, and did pretty well.
I sold it and moved to a bigger place on North Avenue. I
was becoming a tycoon, in a minor league way, in the auto
business. I should have stayed in that league.
My brother, Tommy, and I bought our father a two-
flat building at California and Warren, where he could be
independent and make a small bet now and then. He died in
1926 on a trip to California, the same year Clara's and
my first son was born. That's nature's way of evening things
up, I guess; like when one guy goes into the penitentiary
and another guy gets paroled to make room for him.
My wife and I moved from Oak Park to another sub-
urb, Des Plaines. I bought a place that some of the news-
papers later called a "mansion" or a "gang fortress." It
was a six-room bungalow and later I put a 60-foot
swimming pool in the back. The only gang I ever had
around there was a guard with a shotgun after the Capone
mob tried to kidnap my kids.
A bargain in trucks got me into the prohibition beer
business by chance. I bought eight of them, sold six, and
wound up with two sitting around my garage, using up
space and showing no profit.
It happened that I knew most of the bootleggers and
saloon owners in my area. Why not? They were the guys
who had money to buy fancy cars. If Chicago's best stores
catered to them and their wives, why shouldn't Roger
I called on a few saloonkeepers and then made a deal
with two young lads who would work hard to make a buck
or two. Also, I fixed it to buy beer from two breweries
which turned out legal one-half of one per cent prohibi-
tion beer—and sneaked good brew out the back door.
My trucks hauled the beer, the drivers made a profit of
twenty dollars a barrel, they paid me a percentage on the
purchase price of the trucks and everybody was happy.
The police generally expected a payoff of $5 a barrel
for beer being run into any given district. I didn't pay it and
neither did my drivers. Our operation was too small for the
law to bother much with us.
And then Tubbo Gilbert stepped into the picture. I had
known him for a long time, first as a labor skate and later
as a ward politician. We never got along well and, later on,
he swore that he couldn't remember having seen me until
July 19th, 1933, an important date in my life.
Anyway, Tubbo, a sergeant at the time, stopped one of
my beer trucks, carrying three barrels of beer, arrested the
driver and took the beer to his stationhouse.
The payoff was that the beer in the^ barrels was legal
stuff—a half of one per cent. It was no more illegal than
lollypops or baby Pablum, and it carried about the same
kick. He had to release the driver, the beer and the truck,
I circulated the story around Chicago and the back of
Tubbo's neck turned red as a gobbler turkey's wattles in
Gilbert liked me even less after that. It took him a
long time to get even with me, but he finally did—99
years of even.
One of my friends at the time of Tubbo's near-beer
humiliation was Matt Kolb, a bootleg beer distributor with
a saloon on California Avenue, not far from my garage.
He was a fat, gentle old gent who weighed about 220
pounds, beer belly and all. Anybody who thought all
bootleggers were gangsters with machines guns and gun
molls had only to meet Matt. He would run away from a
ten-year-old kid armed with a flyswatter.
I sold Kolb a car, giving him a good deal and splitting
the commission with him, a thing all dealers did then to
promote sales. Matt came to me a few months later with
a proposition. He had a partner, but they weren't getting
along. I could buy out the partner for $10,000. Kolb once
had been tied up with the Capone mob, but violence had
scared him away.
My automobile business then was bringing me in from
$50,000 to $60,000 a year. But the big money was in
alcoholic beverages. Everybody in the racket was getting
rich. How could the bootleggers miss, with a short ounce
of gagging moonshine selling for $1.25, or an eight-ounce
glass of nauseating beer going at 75 cents?
I drew $10,000 from the bank, handed it to Kolb and
said: "You got a new partner."
My next on-the-job training in oil was as a telegrapher
for the Empire Pipe Line Company at Ardmore, Okla-
homa, and there I learned the big words about petroleum
—plus a few names to drop.
The Sinclair Oil people, in a moment of laxity, hired me
as a scout.
The experience I had had in that line was confined to
watching silent western movies in which Army scouts
killed Indians. But what the hell, I was an oil field en-
gineer, wasn't I? And I could talk as good a gusher as the
original Carbon Petroleum Dubbs.
Word came to me that a famous New York geologist,
Dick Raymond, needed a helper. He had located oil fields
all over the world. I went after the job and got it. It put me
in the big money.
Raymond and I drove all through southwest Oklahoma.
At each county seat town, we would get a plat, or dia-
gram, on oil leases, along with figures on production of