(1900-1933): Assassin
Joseph Zangara is always listed as and was executed
as the would-be assassin of President-elect Franklin
D. Roosevelt and the killer-by-mistake of Chicago
mayor Anton Cermak. However, a strong minority
view is that Zangara never wanted to kill FDR — con-
trary to his own later confession — but was a hired
Mafia hit man assigned to shoot Mayor Cermak
while he was with the president-elect in Miami in
February 1933. Indeed, Judge John H. Lyle, gener-
ally held to be the most knowledgeable non-Mafia
man on Chicago crime, stated categorically that
"Zangara was a Mafia killer, sent from Sicily to do a
job, and sworn to silence."
Cermak, elected as a "reformer," was anything
but that. He waged war on the Capone Mob (at the
time Big Al was already in prison) but not so much
to clean up the city as to replace the Capones with
his own gangsters, headed up by Teddy Newberry.
He moved against Frank Nitti, Capone's at least titu-
lar successor, once Big Al was behind bars. In fact,
court testimony later indicated that the mayor had
dispatched some "tough cops" to erase Nitti, which
they attempted to do after handcuffing the unarmed
gangster. Nitti was shot three times in the back and
neck but miraculously survived, whereupon the
mayor of America's second city hurriedly left his
bailiwick for Florida.
The way the theory goes, Nitti had Newberry
killed and then sent a hit man — Zangara — to take
care of the mayor. Considering the fact that the
mayor had left Chicago on December 21, 1932, and
was still in Florida on February 15, 1933, it is con-
ceivable that he might not have been planning to
return at all, figuring Florida sun was preferable to
Windy City lead.
On February 15 Cermak was in an open car with
FDR in Miami when Zangara opened fire, fatally
shooting the "wrong man" Cermak. Yet Zangara
had won several pistol-shooting awards when he was
in the Italian Army. The fact that he of all people
failed to hit the president-elect led some crime
observers to believe that he might have hit his real
target after all. Lingering in his deathbed for three
weeks, Mayor Cermak declared he had no doubt
that he had been Zangara's real target.
Why had Zangara missed FDR? According to
press accounts, his failure was due to the alert reac-
tions of fearless spectators who grabbed his arm and
shoved it upward as he began to fire. Privately Zan-
gara contradicted this version to his lawyers, saying
his arm had not been seized until he had gotten off
all his shots. A policeman who helped bring him
down confirmed this version of the events. It made
the theory that he had hit his target all the more
Zangara ranted and raved against capitalists, yet
there was nothing on the record to indicate he was
an anarchist, communist, socialist or even Fascist.
Despite all his ravings previously against "capitalist
presidents and kings," Zangara turned out to be a
registered Republican.
Joseph Zangara was almost stripped of all his clothing
after being seized in his unsuccessful attempt to
assassinate President-elect Franklin D. Roosevelt. Some
have insisted Zangara was a Mafia hit man who did get
his actual target, Chicago mayor Anton Cermak.
For two years before the shooting Zangara had
lived in Florida, his main occupation seeming to be
betting on horses and dogs. One researcher on Zan-
gara, the Reverend Elmer Williams, wrote that Zan-
gara had worked in a syndicate "cutting plant" in
Florida "convenient to a canal where the whisky was
run in from the islands." Williams's thesis was that
Zangara got in trouble with his underworld employ-
ers and was given the choice of being tortured and
murdered himself or killing Cermak.
Of course Zangara went to the electric chair pro-
claiming his pride with his act, insisting he had
wanted to kill FDR. He said of Cermak, "I wasn't
shooting at him, but I'm not sorry I hit him."

Was that the real Zangara speaking or the Mafia
hit man sticking to his cover story? If it was the lat-
ter, it was hardly unbelievable. The mob always
could draw on such unlikely sources ready to lay
down their lives in some secret agreement. In The
Godfather Mario Puzo tells of the Bocchicchio fam-
ily, which permitted one of its members to confess to
a murder he hadn't committed and go to the chair for
it. That was fiction but it was hardly outside the
behavior patterns within certain Sicilian Mafia fami-
lies. The family was made an offer, a reward, it
couldn't refuse. Had Zangara got an offer he too
could not refuse? The majority view says no, that he
was a political assassin, period. There are those in
law enforcement and the underworld who laugh at

TOUHY, Roger "Terrible"

(1898-1959): Bootleg kingpin
It has been said by some observers of the syndicate
crime scene in America that FBI chief J. Edgar
Hoover may have done the wise thing to pretend for
decades that organized crime and the Mafia did not
exist. The case of Roger "Terrible" Touhy demon-
strated that the FBI did not fully comprehend the
nature of such criminals and that the agency was
used and abused by organized crime in framing
The FBI may be said to have never understood
poor Roger the Terrible. When they went after him
in lieu of dozens of other more terrifying gangsters,
they picked on a man whom the Chicago Crime
Commission never had on its roster of public ene-
mies, and, as a federal judge would later note in a
major finding, had never even been associated in any
way with a capital offense.
Yet amazingly, just as Touhy proved a thorn to the
FBI, he was equally regarded as a true terror by Al
Capone, who regarded Touhy as one of the stum-
bling blocks to his plans to organize all crime in
Roger "Terrible" Touhy was pretty much a cre-
ation of sharp public relations, his own. As far as the
entire underworld had it figured, the Terrible
Touhys — Roger, the boss, and his five brothers — con-
trolled all booze operations in the Chicago suburban
area of Des Plaines and had their empire backed with
such firepower that they were impregnable.
Press coverage indicated the Touhy Gang to be
about the most vicious in the Midwest. Yet Touhy
was a middle-class bootlegger, one who employed no
more muscle than necessary to convince all the
speakeasies and saloons in his area to handle Touhy
beer and booze exclusively. Indeed, firepower was
less a reason for Touhy's success than his ability to
handle the fix as well as any figure in the under-
world. Not only was Touhy the master of the fix, but
he knew how to supplement cash payoffs with fringe
benefits that meant so much. He rewarded the local
politicians and police brass with bottled beer brewed
especially for them and often bearing their own per-
sonal labels.

Perhaps Touhy's reputation as a ferocious gangster
was sealed by his looks — kinky-haired, beady-eyed,
with a hawklike face, clearly a man to be feared. And
Touhy knew how to act the part, forcing even Al
Capone to back down to him. Touhy had once sold
the Capone boys 800 barrels of his superior beer for
$37.50 a barrel (his cost of production was $5.50 at
most), and Capone then tried to short Touhy with
$1,900 in the payoff, claiming that some of the bar-
rels had leaks. (Capone always pressured people that
way.) Touhy came back with his regular routine. He
assumed his famed hard stare, and said softly, "Don't
chisel me, Al." Capone paid the $1,900.
Roger and his five brothers had not started out as
criminals. They grew up in respectable circum-
stances, the sons of a policeman. In the early 1920s,
the Touhys went into the trucking business, "strictly
legit," at least by Touhys word. Business, however,
did not boom until they started filling the trucks with
beer. The Terrible Touhys raked in a fortune.
Roger Touhy took control of the Des Plaines area
in the northwest section of Cook County. In those
days a bootlegger was hardly an unpopular figure,
and Touhy found ways to increase the esteem in
which he was held. He kept out lowlife criminals and
especially clamped down on brothels. Whenever a
group of mobsters tried to open a roadside whore-
house, Touhy would relieve the local police of the
need to take action. He sent in his own enforcers to
wreck the joint. Even when Capone personally noted
that Des Plaines was, as he charmingly put it, "virgin
territory for whorehouses," Touhy's response was his
hard-eyed stare, which convinced Capone to drop his
Whenever rivals made noise about wanting to
move in, Touhy would invite them to his headquar-
ters for a visit, where they were greeted by what
appeared to be an armed camp, the walls lined with
submachine guns. What the visiting hoods didn't
know was that the weapons had been made available
by cooperative local cops just for a good show. While
the gangsters were conferring with Touhy, underlings
would come rushing in for weapons, mumbling
something about having a great chance to rub out
some party. Touhy would nod his head slightly in
assent and return to the dialogue as though the mat-
ter was of minor importance. When Touhy's visitors
left, they were fully convinced they would be the
loser in any war with the Terrible Touhys. At various
times such Capone gunners as Murray "the Camel"
Humphreys and Frank Nitti were so shaken that they
reported back that Capone would be facing a terrible
bloodletting if he tried to move in.
Still the Capone gang tried to get Touhy — even
after Big Al went to prison. Deciding violence was
out, they resolved to use another method, helping the
law get something on him. Suddenly Touhy found
himself in big trouble with the FBI. It is unclear if the
Chicago Outfit had anything to do with the first inci-
dent, but it is not beyond the realm of possibility.
Touhy and several of his henchmen were arrested for
the kidnapping of William Hamm Jr. The FBI
announced it had a strong case against Touhy, but a
jury thought differently, finding him not guilty. Later,
the FBI switched the charge to the real culprits, the
Barker-Karpis gang. By coincidence Alvin "Creepy"
Karpis had long been close to the Capone Gang.
Next the FBI arrested Touhy for the alleged 1933
kidnapping of Jake "the Barber" Factor, an interna-
tional confidence man with ties to the Capones. This
was despite underworld grapevine information that
indicated the abduction was a fake masterminded by
Factor and the Capones. Special agent Melvin Purvis
announced that his arrest of Touhy in the Factor
snatch was a landmark in the art of detection. "This
case," he said, "holds a particular interest for me
because it represents a triumph of deductive detective
work. We assumed from the start, with no material
evidence, that the Touhy gang was responsible for
the crime."
Touhy's first trial ended in a hung jury. He was
convicted the second time around and was sentenced
to 99 years. Touhy went to prison screaming frame-
up while the Capones swarmed into Des Plaines.
In 1942, Touhy escaped from prison but was
recaptured soon and saddled with an additional
sentence of 199 years. Still, there were many per-
sons, including several journalists, who considered
him innocent of the Factor kidnapping, and took up
the fight to clear him. In the 1950s Touhy at last
won a rehearing on his original conviction. After a
searching inquiry lasting 36 days, Federal Judge
John H. Barnes ruled that Factor had not been kid-
napped at all but had disappeared "of his own con-
nivance." Judge Barnes had plenty of criticism to
hand out to several quarters, especially to the FBI,
the Chicago police, the state's attorney and the
Capone Gang. It took a few more years of legal
jockeying before Touhy was released. He collabo-
rated on a book, The Stolen Years, about his ordeal.
Just 23 days after Touhy won his freedom, he was
gunned down as he was entering his sister's house in
Chicago. As he lay dying, the former gangster mut-
tered: "I've been expecting it. The bastards never
The underworld had no doubts about who had
knocked off Touhy — the word was the price on his
head was $40,000 — that it was the handiwork of
longtime Capone mobster Murray "the Camel"
Humphreys. Six months after the Touhy rubout,
Humphreys bought 400 shares of First National Life
Insurance Co. stock at $20 a share from John Factor,
Touhy's old nemesis, and a man at the time eager to
have an unsullied slate as he was attempting to oper-
ate in Las Vegas. Eight months later, Humphreys sold
the shares back to Factor for $125 a share, turning a
profit of $42,000 in capital gains. The IRS looked at
the transaction and related details and declared that
the $42,000 was clearly payment for services ren-
dered and that it was subject to full income taxes.
The Humphreys-Factor financial dealings were
not the only noteworthy matter occurring after
"Terrible" Touhy lies dying after being shot. Released
From prison after doing 25 years on a mob frame-up, he
said, "I've been expecting it. The bastards never forget."
Touhy's death. Early in 1960, a few months after the
murder, retired FBI man Purvis committed suicide.