Although it is not the first place you would think of having a spy pedigree – Chicago, Illinois – smack dab in the middle of the United States, does have a few notable spy connections.

Over the next two posts I will discuss some of the real and fictional spies we’ve seen in Chicago.

True spy stories of Chicago

The heyday of real spies in Chicago was back in the late 1800’s when two men who became best known for their spy exploits were active in the city.

Allan Pinkerton – The first of the Chicago spies was Allan Pinkerton. During the Civil War, he served as the head of Abraham Lincoln’s spy network during the Civil War. Spy of the Rebellion, written in 1883, looked at his work as head spymaster. Among his supposed successes was stopping an attempt to kill Lincoln.

In 1885 he founded the Pinkerton Detective Agency in Chicago with the motto “We never sleep.” The agency was created as a response to the growing need by railway and steel magnates for their own security forces. They were worried about keeping their workers under control and hired the Pinkerton Agency to keep them in line. This resulted in many bloody clashes between Pinkertons, as the agents were called, and labor forces trying to unionize.

Eventually Congress was so concerned about the power and motives of the Pinkerton Agency that it passed the Anti-Pinkerton Act specifically to keep the government from being able to hire non governmental agencies for investigations or security services. Given the privatization of both intelligence and the military in recent years, it goes to show that the country has been dealing with these questions for a long time. This 1980 Government Accountability Office report skeptical that companies could offer a quasi-military armed force appears positively quaint now.

Pinkerton went on to “write” his autobiography and his son wrote several novels fictionalizing, or just making up from whole cloth, some of his adventures. It was a powerful act of myth-making to use the early dime novels as a vehicle to show his agents as heroes. Through the magic of ebooks and copyright expiration most of these can be found online for free and have such tantalizing titles such as The Expressman and the Detective, The Molly Macguires and the detectives and The Spy of the Rebellion.

Many of the positive myths of Pinkerton and his agency, such as foiling an attempted assassination on Lincoln and the hunt for Jesse James, have not held up to scrutiny over time. Historian S. Paul O’Hara goes into the myths and the truths of the Pinkertons in his book Inventing the Pinkertons and talks more about the legacy of the Pinkertons here.

Henrì Le Caron – In the mid to late 1800’s the Fenian Brotherhood was created in America. Its aim was to engineer the release of Ireland from the rule of Britain via raids on Canada, then still a province of the United Kingdom. Making his way into this was Henri Le Caron. Le Caron’s real name was Thomas Miller Beach and he came to America from England to fight for the Union in the Civil War, changing his name at that time. He settled in the US after the war working as a doctor and became acquainted with some Fenians. When a British MP found out about his connection to Fenians, Le Caron was persuaded to spy for the British government on the Fenian movement in America. He did this for an extraordinary 25 years starting in the 1860’s until the late 1880’s providing important information to foil several attacks that had been planned. He lived in Wilmington, Illinois close to Chicago and visited the city often.

In 1889, his cover was blown due to an investigation into the Irish nationalist movement called the Parnell Commission. Le Caron became quite the celebrity and a polarizing figure subject to death threats. He was given the moniker of ‘Prince of Spies’ and went on to write a book about his experience called Twenty Five years in the Secret Service.

I highly recommend this article on Le Caron and his spying by historian Joseph Clark that does a great job discussing the politics of the time and the effect this spying had on the Irish movement. There is an also an exhaustive website looking at his exploits.

Moe Berg – Berg was a catcher for the Chicago White Sox for several seasons in the late 1920’s before working for the OSS during WWII and had his story told in The Catcher was a Spy by Nicholas Dawidoff. He spoke several languages, graduated from Princeton and Columbia and was known for being extremely intelligent guy but a not so great a ball player.

His greatest claim to spy fame is researching various Yugoslavian resistance groups after parachuting into the country, a very Bondian moment, as well as using that well known intellect of his to visit various European physicists to determine how fair Germany was on a nuclear bomb. A movie adaptation of the book was released starring Paul Rudd and has received respectable, if not glowing, reviews.

Herbert Hans Haupt – Chicago was where the Nazis put Operation Pastorius into action. The plan? Recruit spies who could blend in with Americans, send them to the US via submarine with money and explosives and have them sabatoge crucial US locations. One of the recruits was 22 year old American citizen Herbert Haupt. Brought to the US by his German parents and then made a naturalized citizen he left Chicago for Germany in 1941. He and 7 other spies were sent by sub from Germany, half headed to New York City, half to Chicago. The New York bunch turned themselves in to the FBI and Haupt and his fellow spies were rounded up quickly upon there arrival in the city before they could put their plan to steal plans for a bombsight that was one of the nation’s most closely guarded secrets. Haupt arrived in Chicago in late June and by August he was dead, sent to the electric chair for treason. His parents were also charged and later deported to West Germany. More here, here or in Saboteurs: The Nazi Raid on America by Michael Dobbs.

Ernest Hemingway – Hemingway has at various times been said to be both a KGB spy and a spy for the CIA. Talk about playing both sides against the middle.

Born in 1899 and raised in Oak Park, Illinois, a suburb just outside of Chicago, he ended up in Europe driving an ambulance during World War I, coming back to the US and establishing himself as a writer before going to Spain during the Spanish Civil War which is what first brought him to the attention of the Soviet Union. Later in life he ended up in Cuba, which was a hotbed of spy activity as the Cold War heated up. Nicholas E. Reynolds recently wrote Writer, Sailor, Soldier, Spy: Ernest Hemingway’s Secret Adventures, 1935-1961 looking at that particular aspect of his life.

Thomas Miner –  This story from 1977 in the Chicago Reader brought Thomas Miner to light as a Chicago man whose company provided cover to CIA operatives.

The article tells the story of how the CIA used (uses?) legitimate companies and in return these companies received lucrative contracts from the government. It’s an interesting read and insight into the how the CIA did business in the 60’s and 70’s.

Robert Hanssen – One of the most infamous spies in recent years, Robert Hanssen was born in the city and the son of a Chicago Police officer. He tried a number of different jobs, from accountant to dentist before finally landing work as an investigator for the Chicago PD. He was then able to use that position as a jumping off point for a job with the FBI.

Hanssen began working as a spy for the USSR in 1985, the same year as Aldrich Ames, and together they became a matching set of FBI/CIA traitors who, when taken together, did tremendous damage to the intelligence agencies of the United States. After ransacking the Bureau’s secrets for over 20 years he was finally captured but not before the FBI spent five years investigating an innocent CIA officer. The story was turned into the film Breach and has been told in numerous books.

Know of a Chicago spy I missed? Please let me know in the comments.

Part two, where I look at Chicago writers of spy novels and at spy novels set in Chicago is here.