The Nazi Saboteur on Fremont Street

The apartment building at 2234 North Fremont Street has been renovated, but it’s still the same building.  On the morning of June 27, 1942, Herbie Haupt walked out the front door and into history.

2234-n-fremontHaupt was 22 years old.  He got into his new Pontiac and drove a block south to Webster, then turned right.  At the ‘L’ underpass another car forced him to the curb.  Three FBI agents emerged from the second car and placed him under arrest.  He was charged with being a German spy.

The U.S. had been at war with Nazi Germany for about seven months.  Haupt was one of eight men who’d been dropped off the Atlantic coast by submarine a few days before.  Their mission was to blow up American defense plants and transportation facilities.  The plan had been personally approved by Adolf Hitler.

Herbert Hans Haupt was born in Germany in 1920.  His family moved to Chicago when he was a boy.  He became an American citizen at age 10, and later went to Schurz High School.  While there he belonged to ROTC.

Haupt was in Germany when his native country declared war on his adopted country.  His explanation for this was vague.  He never denied that he’d been part of the sabotage mission.  He claimed to have joined the plot only so he could get back home to America.

The eight spies had landed in two groups.  One unit came ashore in Long Island, the other in Florida.  Soon afterward, two men from the first group decided to abandon the mission.  One of these men contacted the FBI.  The FBI began tracking the others.hhaupt

Haupt was part of the Florida group.  Along with another man, he took a train to Chicago.  The two of them were supposed to settle in and prepare for the next phase of the mission.  Haupt went to his parents’ apartment on Fremont Street.

Did they wonder why Herbie suddenly appeared?  They didn’t ask, he didn’t tell.  He seemed to have plenty of money.  He bought a new car.  He began dating a neighborhood girl.

Then the FBI nabbed him.

President Franklin D. Roosevelt ordered the eight terrorists be tried by military tribunal.  Their lawyers attempted to get the cases moved to civilian courts.  The U.S. Supreme Court denied the appeal, saying the accused were “unlawful combatants.”

All eight men were quickly found guilty and sentenced to death.  Roosevelt commuted the sentences of the two Germans who’d dropped out, giving them prison time for illegally entering the country instead.  The other six—including U.S. citizen Herbie Haupt—died in the electric chair on August 8, 1942.

In recent years, the Supreme Court ruling in the Nazi terrorist case has become part of the discussion about the Guantanamo detainees.  The building where Herbie Haupt spent his last hours of freedom is privately owned.

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2 Responses to “The Nazi Saboteur on Fremont Street”


  1. 1 Garry December 27, 2016 at 12:22 pm

    Don’t forget about the local Nazi idiot that had himself crucified after the war, on the L pillars, not that far away.

    • 2 J.R. Schmidt December 27, 2016 at 3:04 pm

      Good memory! It happened on March 9, 1945. I described that incident in my book On This Day in Chicago History. For anyone who hasn’t yet bought the book (why not???), I also did a post about it on this website. Just type “crucifixion” in the search box.
      –JRS


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