Bootleggers, Backwaters and Bears: A Glimpse Into Iowa’s Prohibition History

In 1920, the United States entered prohibition. From 1920-1933, it was illegal to produce, import, transport or sell alcohol. Iowa's bootlegging history is a patchwork of colorful characters who turned necessity into enterprise during prohibition. Nestled between two major rivers and with access to an abundance of corn and rye, Iowa bootleggers took advantage of the state's opportunities during the Prohibition Era.

Bootleggers utilized the river's secluded backwaters and isolated islands to work beyond prying eyes. Freedom Jacobs of Clayton, Iowa exemplified this resourcefulness, keeping his operation mobile by running his still from a houseboat.

Some bootleggers took to the skies, employing small aircraft to land in remote areas, deliver their product, and escape before authorities could catch them.

Others, like Peter and George Dinglebary simply used what nature provided on their own property—a spring-fed pond and rapid creek that flowed through their land, providing perfect cover and necessary resources.

Many bootleggers led double lives. Edward Doll, also known as Edward LaRue, ran a small lunch counter in Burlington, Iowa, often taking "business trips" that later revealed his true occupation—while caught transporting stills in Nebraska in 1924.

While most kept their operations discreet, Kenneth Sonderleiter broke the mold: brazenly promoting himself and advertising where to purchase his product. His audacious approach led to shootouts and car chases with authorities. To eliminate competition, he even disguised himself as a federal agent to intimidate a rival bootlegger.

Law enforcement faced their own challenges during this time. Officers knew where speakeasies operated but needed to catch them with alcohol to make arrests. In 1932, federal agents in Sioux City, Iowa, described entering establishments and making no arrests—instead marveling at the ingenious methods developed to quickly destroy evidence during raids.

When bootleggers were caught and their operations dismantled, most couldn't afford the fines. Yet many found ways to resume their trade upon release. Eventually, larger competition, the inherent dangers, or persistent law enforcement would catch up with them.

Our friend Kenneth Sonderleiter eventually served his time and settled into legitimate business, running a penny arcade, lunch stand, and small zoo. He made headlines again in 1945, but for an entirely different reason—helping capture an escaped polar bear from a train near Boone, proving that Iowa's bootleggers were nothing if not versatile.

Transcript

Bootleggers, Backwaters, and Bears: Iowa’s Prohibition outlaws didn’t just break the law — they refined it.

Iowa's bootlegging history is a patchwork of colorful characters who turned necessity into enterprise during Prohibition. Renowned for their ingenuity, these Iowans leveraged the state's

location between two major rivers, rural landscapes, and abundant corn and rye to create an ideal setting for illicit alcohol production and distribution.

Along the Mississippi River, locals claimed: "The Kentucky mountains probably never harbored more stills than the hills and islands of the Mississippi along northeastern Iowa."

Bootleggers made use of the river's secluded backwaters and isolated islands to work beyond prying eyes. Freedom Jacobs of Clayton, Iowa exemplified this, keeping his operation mobile by running his still from a houseboat.

Others took to the skies, employing small aircraft to land in remote areas, deliver their product, and to escape before authorities could catch them.

Peter and George Dinglebary (B-a-r-y, but also sometimes spelled the other way), simply used what nature provided on their own property—

a spring-fed pond and rapid creek that flowed through their land, providing perfect cover and necessary resources.

Some lived double lives. Edward Doll, also known as Edward LaRue, ran a small lunch counter in Burlington often taking "business trips" that later revealed his true occupation when caught transporting stills in Nebraska in 1924.

While most kept their operations discreet, Kenneth Sonderleiter broke the mold: brazenly promoting himself and advertising where to purchase his product.

His audacious approach led to shootouts and car chases with authorities.

To eliminate competition, he even disguised himself as a federal agent to intimidate a rival bootlegger.

Law enforcement faced their own challenges. Officers knew where speakeasies operated but needed to catch them with alcohol to make arrests. In 1932, federal agents in Sioux City

described entering establishments and making no arrests—instead marveling at the ingenious methods developed to quickly destroy evidence during raids.

When bootleggers were caught, their operations dismantled, most couldn't afford the fines. Yet many found ways to resume their trade upon release.

Eventually, larger competition, the inherent dangers, violence, or persistent law enforcement would catch up with them.

Our friend Kenneth Sonderleiter eventually served his time and settled into legitimate business,

running a penny arcade, lunch stand, and small zoo. He made headlines again in 1945, not for bootlegging — but helping capture a polar bear the escaped from a train near Boone,

proving that Iowa's bootleggers were nothing if not versatile. Cheers!

Do you want to learn more? Step back into the Roaring Twenties and join us for the Prohibition Party on July 13th, from 2 to 4 p.m. at Ken’s Speakeasy located inside the Iowa Taproom in Des Moines' East Village.

You and a guest will enjoy an afternoon of untold stories from Iowa’s Prohibition era, with author Linda McCann, who will share tales from her book Prohibition in Eastern Iowa. Indulge in food and drinks popular from the time, all in a secret speakeasy setting—don’t forget the password to get in! Make your donation today and be part of this event that's sure to be the bee's knees! Get two tickets to attend the party with your pledge of $150.

Cheers!