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Column: ‘Underbelly’ podcast offers a most compelling tale of a most unlikely spy and his Chicago connections


If you have never met a real spy in person — and who has? — you nevertheless carry an image of a spy in your mind and it may be that of James Bond, Napoleon Solo, Jason Bourne, George Smiley or maybe some combination of those and others.

There are a lot of fictional spies but none of them can prepare you for Dave Rupert, the compelling real-life centerpiece of a 12-part podcast series called “Underbelly: The Rebel Kind,” currently unfolding on various platforms.

New episodes come every Wednesday, each roughly an hour in length. I certainly don’t want to spoil any of the edge-of-your-chair excitement of this tale, and though I was not an enthusiastic podcast fan until this show, I will do my best to get you to plug into this audio marvel without giving away many of the details that will keep you hooked.

In addition to having no experience with espionage and without political or religious affiliation, Rupert was not exactly the blend-into-the-wallpaper type. He was a giant, standing 6 feet, 7 inches tall and weighing 350 pounds, give or take.

Still, he would become one of the most successful spies in FBI history. It was he who in the late 1990s was responsible for infiltrating and taking down the Real Irish Republican Army, a particularly violent faction of the IRA, and its most notorious terrorist, Michael “Mickey” McKevitt, convicted of directing terrorism in a 2003 trial and sentenced to 20 years in prison.

You will learn of Rupert’s childhood in upstate New York; his checkered career; legal and financial troubles and about the night he walked into an Irish bar in Florida. There he met a woman who would become his wife and take him on trips to Ireland, which he loved and where he met all manner of companionable people, many of whom were in the dangerous business of creating trouble and terror.

At one point he was here, running a trucking company in Canaryville, when in walked an FBI agent and, based solely on a photo he had of Rupert with an IRA operative in an Irish pub, recruited him to become a spy.

No training, no “spy skills” but with a certain adventurous streak, Rupert accepted and for the next seven or so years climbed deeper into the IRA and, with the FBI buying him a pub in Ireland, began providing information not only to the FBI but MI6, the British intelligence service.

When his work was done and never one to pass up an opportunity, Rupert thought there might be a book in his “adventures.” He contacted then-Tribune reporter Flynn McRoberts who, with Abdon Pallasch of the Chicago Sun-Times, began to interview and research Rupert. McRoberts had to pull out of the project due to other professional commitments and a new job with Bloomberg News. Pallasch then teamed with colleague and friend Bob Herguth.

They turned on a tape recorder for hours and hours. But for reasons you will learn when you listen to the podcast, the book deal never came to fruition. They were sued to give up the tapes of their Rupert interviews and soon enough Pallasch and Herguth went back to separate careers.

Herguth, a long-time investigative reporter with the Sun-Times, focuses on many subjects, including police corruption, organized crime and government accountability, as well as religion. Pallasch was a reporter for the Sun-Times, where he covered a young Barack Obama and co-wrote (with Jim DeRogatis) the stories that paved R. Kelly’s road to prison. He left the newspaper business to work in government, where he is now communications director for the Illinois Office of Comptroller Susana Mendoza.

Rupert faded into a colorful memory until about three years ago when Herguth was contacted by a producer with an outfit called Entropy Media. They discussed various ideas. The producer was sparked by Rupert and the seeds of this podcast were planted.

Entropy is the creation of a former Chicagoan, Anjay Nagpal, who attended Fenwick High School before going off to become a Hollywood movie producer. With Entropy he began to make podcasts. The first was “Underbelly: “Brokers, Bagmen, and Moles” based on wild tales from the 1980s Chicago trading floors and an FBI undercover sting operation against alleged broker fraud.

Pallasch and Herguth began working on this project more than two years ago. “It took us to Ireland and elsewhere,” says Herguth. “We were knocking on doors, doing some original reporting.”

This is a podcast of the most compelling kind, produced by Dalton Main. What makes it valuable beyond its edge-of-the-seat, thriller-like qualities is its substance and breadth. It’s a layered story, employing the voices of scholars and other enlightening folks. There is music, the history of Ireland, the Troubles and Chicago’s deep and often dark connections to Ireland. Some thoughtful portions deal with the complex political and emotional issues at play, the personal costs of conflict and betrayal. It’s an exciting story but a human one too. Pallasch and Herguth, from a script written in collaboration with others, sound polished, professional.

“They made us sound better than we actually sound,” said Pallasch.

He and Herguth are pleased.

“I really think this podcast is better than any book might have been,” says Pallasch. “There are so many layers to get, making for a powerful narrative.”

Rupert isn’t saying a word. His work earned him the FBI’s Lou Peters Award in 2013 and millions of dollars too and he now lives someplace in the United States. One hopes he has a quiet life, out of harm’s reach.


Rick Kogan , 2024-05-08 12:45:49

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