America in the 1920s and ’30s was wide open to criminals. The era produced bootleg whiskey, bank robbers, and folk-hero bandits who sometimes drew bigger cheers than the police chasing them. In this issue, we spotlight a luckless gangster who couldn’t catch a break and an FBI legend whose life spanned more than a century.

We’re Dan Williams and M. J. Van Deventer, co-authors of the forthcoming true crime book Madeline Gets Life. As a bonus, you can hear a rare audio clip of our title character, Madeline Webb, recalling how she stood up to a childhood bully.

The Unluckiest Mobster

Above: Roger Touhy is released in 1954 by a federal judge who ruled he was framed for a 1933 kidnapping. An appeals court sent Touhy back to prison after 49 hours of freedom. (Chicago Tribune photo)

Roger Touhy was riding high.

Touhy controlled the bootlegging in the suburbs north of Chicago. It helped that he brewed his own high-quality beer.

Touhy let Al Capone and his Chicago Outfit buy the beer, but the two mob bosses went to war when Touhy refused to give Capone a piece of the action.

In one year alone, more than 100 people were killed. Touhy lost two brothers to gunfire.

In 1933, he was charged with kidnapping William Hamm, president of the Hamm’s Brewery, who was freed after his family paid a $100,000 ransom.

The crime was actually the work of the Barker-Karpis Gang, and Touhy got off.

Then he was tried for another kidnapping – of John “Jake the Barber” Factor, an ally of Capone (and half-brother of cosmetics pioneer Max Factor).

Touhy claimed Factor faked the abduction to avoid extradition to England on fraud charges.

Jurors didn’t buy it. They convicted Touhy and two of his gang in February 1934 and sent them to Stateville Prison in Joliet for 99 years.

But Touhy was right. He was framed by the Chicago Outfit – now led by Frank Nitti after Capone’s conviction for tax evasion – with help from crooked cops such as Dan “Tubbo” Gilbert.

In October 1942, Touhy and six other inmates made a sensational escape from Stateville Prison. Using smuggled handguns, they raided a workshop for ladders and ropes and took control of a guard tower. They ran out the tower’s gate, stole a guard’s car, and vanished.

Touhy’s bad luck reasserted itself less than three months later.

U.S. agents caught up with him and the others in late December after using a wartime draft-registration law to make them federal fugitives.

Touhy had 199 years added to his kidnapping sentence.

He kept challenging his conviction in the courts. Finally, in 1954, a federal judge declared the kidnapping a hoax and ordered him released after 20 years behind bars.

Freedom lasted just 49 hours.

The U.S. Court of Appeals sent him back to Stateville, ruling the judge didn’t have jurisdiction.

Ultimately, Illinois Governor William Stratton bowed to overwhelming evidence and shortened Touhy’s sentences. That allowed the one-time gangster to walk out of prison on November 24, 1959.

Things were finally looking up.

The prison bought him a new suit. His sister put him up at her house on Lotus Avenue in Chicago. And he had a book coming out – The Stolen Years – documenting the frame-up.

On the night of December 16, Touhy was climbing his sister’s front steps when two men with shotguns blasted him in the legs. A bodyguard was also wounded.

Above: Touhy lies mortally wounded after being ambushed in Chicago on December 16, 1959. (Photo by Marshall Marker)

Before bleeding out an hour later, Touhy said, “I’ve been expecting it. The bastards never forget.” He was 61.

After 26 stolen years, freedom lasted just three weeks for the unluckiest gangster.

Sources: The Chicago Tribune, the Minneapolis Star, and the FBI’s history site provided key details for this story. The “bastards never forget” quote comes from the 2002 book The Encyclopedia of Kidnappings by Michael Newton.  

This Month in Mobland Infamy

• October 4, 1931 – “Mad Dog” Coll Nabbed

  • New York police captured mob hitman Vincent Coll, ending a three-month search for the chief suspect in a Harlem shooting that killed a five-year-old boy.

  • Detectives pounced as Coll and an associate stepped out of their suite at the Cornish Arms Hotel on West 23rd Street. They looked relieved their captors weren’t rival gangsters.

  • Mob boss Dutch Schultz was trying to kill Coll, an assassin for Schultz before breaking away to form his own gang.

  • The murder of five-year-old Michael Vengalli earned Coll the nicknames “Baby Killer” and “Mad Dog.” He was acquitted that December after the prosecution’s star witness admitted lying.

  • Five weeks later, Coll was making a call in a drugstore telephone booth when a man opened fire with a Thompson submachine gun. Vincent Coll was just 23.

• October 12, 1933 – Dillinger Busts Out

  • Three men walked into Allen County Sheriff Jess Sarber’s office in Lima, Ohio, asking to interview prisoner John Dillinger. They claimed to be from the Indiana state prison.

  • Sarber asked for ID. Harry Pierpont, the leader, pulled a pistol: “Here are our credentials.”

  • Pierpont shot Sarber in the gut, then smashed him with the gun when he didn’t hand over the keys. Sarber’s wife, Lucy, turned them over.

  • The gangsters freed Dillinger. Sarber died 90 minutes later.

  • Federal authorities named Dillinger Public Enemy Number One. In July 1934, agents tracked him to Chicago and shot him outside the Biograph Theater. Dillinger was 31. Pierpont died in Ohio’s electric chair at age 32.

• October 22, 1934 – “I Am Floyd”

  • Charles “Pretty Boy” Floyd became Public Enemy Number One after Dillinger’s death.

  • He was linked to the June 1933 Kansas City Massacre in which gunmen tried to free a captured fugitive, killing four officers and the prisoner.

  • Floyd stayed on the run for over a year as authorities hunted him nationwide.

  • Agents finally cornered him at a farm in eastern Ohio, flushing him from behind a corn crib. A hail of bullets brought him down.

  • Before dying, he said, “I am Floyd,” and asked who tipped off the authorities. He was 30.

• October 12, 1937 – Brady Gang Ends

  • A shootout in Bangor, Maine, crushed the gang of new Public Enemy Number One Al Brady – and made FBI agent Walter Walsh (below) a legend.

  • Brady, Clarence Shaffer, and James Dalhover had been robbing banks in the Midwest. They came east to buy guns and clips.

  • Their questions at Dakin’s Sporting Goods in Bangor raised suspicions. The manager called the authorities, and the FBI set up an ambush.

  • At 8:30 a.m., Dalhover entered the store to pick up an order. Walsh, posing as a clerk, disarmed him.

  • Shaffer jumped from the gang’s car and ran to the store shooting. Walsh fired five rounds, and Shaffer fell dead in the street.

  • Walsh was hit in the right hand and shoulder. When Brady joined the gunbattle, Walsh cooly switched hands and fired a fatal shot. Brady was 26.

  • Walsh lived to 106. Watch an FBI video honoring him at 101.

Talk Like a Gangster

Nowadays, if someone puts you on the spot, you might suffer embarrassment.

If you were put on the spot in the gangster era, you were dead.

I kept coming across the phrase while researching this issue of the newsletter. Newspapers started using it in the late 1920s and early 1930s as underworld slang for being set up to be murdered. It took on its broader meaning of being placed in an awkward position in the late 1930s.

Other slang terms popularized during the gangster era:

Moll: A gangster’s girlfriend.

Gat: A gun.

Case the joint: Check out a place before a crime.

Get clipped: Be killed.

G-Man: Federal agent, or ‘Government Man.’

What We’re Reading/Hearing

Newsletter recommendation: Murder by Gaslight. Author Robert Wilhelm takes an entertaining look at 19th century killings in America.

I’ve been listening to the audiobook version of Death in the City of Light, David King’s true tale about a serial killer who terrorized Nazi-occupied Paris during World War II. Marcel Petiot was a doctor who preyed upon Jews and resistance fighters who believed he could help them flee the Nazis. The beginning of the end came when firefighters, responding to smelly smoke coming from a mansion Petiot owned, discovered body parts in a basement furnace. Paris police tracked down the murderer with surprisingly little interference from the German occupiers.

M. J. Van Deventer just finished The Alice Network. Two strong women propel Kate Quinn’s novel – Eve Gardiner, who joins the real-life Alice Network in 1915 to spy on the Germans, and Charlie St. Clair, a pregnant American college student who links up with Eve in 1947 to search for a lost cousin. Quinn does a masterful job of telling their stories in parallel and then uniting them when they learn the real – and dangerous – quest they are actually on.

Audio Gem

My favorite anecdote from Madeline Webb’s youth is a story about a boy who made the mistake of chasing her home from school one day. It provides a glimpse of her spunky character — and of her relationship with her doting Daddy, William Webb. The incident probably happened in 1920 when Madeline was eight years old. She recorded the tale for biographer Jack Rogers in the mid-1970s.

Take a listen: 5 minutes

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