Podcast adds to storied saga of Madrid native's spy adventure

Apr. 13—WATERTOWN — A 12-episode podcast told by two veteran investigative journalists explores how Madrid native David G. Rupert went from a debt-ridden businessman to an undercover agent in order to infiltrate and to help take down a violent faction of the Irish Republican Army.

It's the latest media project focusing on an aspect of the life of Rupert, a former Massena businessman turned international spy who now lives at an undisclosed location. A movie version of his spy stint is also a possibility. The podcast comes four years after the book, "The Accidental Spy" by Irish journalist Sean O'Driscoll was released. In the book, after years of living in semi-isolation, Rupert and O'Driscoll explained how a trucker, working in Chicago at the time, ended up being recruited to the FBI and MI5 at one of the most crucial moments in British political history.

Last March, the one-hour documentary "I Spy" premiered on BBC One Northern Ireland.

It was Rupert's first television interview, telling BBC journalist Jennifer O'Leary his extraordinary story as an FBI/MI5 agent who went inside the Real IRA and sent its leader to jail.

In 2013, Rupert received the Lou E. Peters Award, the FBI's highest public service award, presented jointly by the FBI and the Society of Former Special Agents to recognize individuals who assist the FBI without thought of personal gain.

"Underbelly: The Rebel Kind" podcast is the second installment of Entropy Media's "Underbelly" series. The first, "Underbelly: Brokers, Bagmen and Moles" is a tale of 1980s Chicago trading floors and the FBI's undercover sting operation against alleged broker fraud. It has garnered nearly 1 million downloads and set a high bar for the podcast company launched by film veteran Anjay Nagpal. Most recently Nagpal was chief content officer for Bron Studios, where he managed the financing, development, production and sales of many commercially successful and critically acclaimed films including "Joker," "Bombshell" and "The Green Knight." He started his career as a financial derivatives trader in Chicago.

In "The Rebel Kind," journalists Bob Herguth and Abdon Pallasch recorded Rupert at undisclosed locations. As reported by the Watertown Daily Times in 2020 following the release of the book, "The Accidental Spy," Rupert, a 1968 graduate of Madrid-Waddington Central School, went into the FBI's witness protection program in August 2003 after Ireland's no-jury antiterrorism court convicted the quartermaster general of the guerilla group Real IRA, Michael McKevitt, for directing terrorism. Prosecutors said the organization's car bomb in Omagh, Northern Ireland, killed 29 people in 1998. McKevitt died in 2021.

Herguth is an investigative reporter with the Chicago Sun-Times, focusing on an array of subjects, including police corruption, organized crime and government accountability.

Pallasch was a reporter for the Chicago Sun-Times, where he covered Barack Obama's rise to the presidency and co-wrote the stories that ultimately landed R&B superstar R. Kelly in prison. He now handles communications for the Illinois Office of Comptroller and works on journalism projects in his spare time.

The recordings in "The Rebel Kind" were made on a micro-cassette recorder more than 20 years ago and "never played publicly before."

Rupert, contacted by the Times last week, explained in an email: "Due to some FBI matters, I had to drop my involvement with Abdon and the book. The deal was I gave them two years to use what I had given them to write a book and they didn't."

"I can't say where the tapes were recorded," Pallasch says in the first episode, "because Dave Rupert is still in hiding to this day."

The first episode of "Underbelly: The Rebel Kind" was released on March 13. Episodes have been released weekly since then. Episode 1, "There Once Was a Trucker From Chicago," sets the scene for the series: "Meet Dave Rupert. A guy born in a part of upstate New York so rural it's practically Canada, with a past nearly as untamed: trucker, one-time professional wrestler, pilot, a bit of a serial entrepreneur. Meet Mickey McKevitt. An ocean away, he leads the Irish Republican Army's terrorist splinter cell, the Real IRA. The two men had seemingly nothing in common, but by the time they met, Dave had earned the trust of the group as though he was an Irishman himself."

In the series, listeners will hear about the risks Rupert faced, the challenges he overcame, along with the romances, friendships and sacrifices he made along the way. Pallasch and Herguth worked with veteran podcast producer Dalton Main to bring the story together.

Main said he was approached by Herguth and Pallasch and others at Entropy Media to see if he was interested in joining "The Rebel Kind" project.

"They told me a little about Dave's story and what's been going on for the past 30 years that has been part of his life," Main said in a phone interview from Chicago. "I was just fascinated by it. I thought it was such a compelling tale of putting yourself out there. I was immediately sold on being part of telling his story and getting across the fascinating aspects of it. It's a story that at every turn is unexpected. When I started doing research on it, I found that every aspect of the story and almost every aspect of Dave's life is just unexpected."

Main said that he also found the "centuries-old conflict" that Rupert wandered into fascinating.

"It's much more nuanced than it's ever been portrayed in most popular media," Main said. "It was never that simple and it was always a complicated, sort of messy situation that had a lot of intrigue and caught a lot of peoples' lives in the crossfire. Dave became one of them and it was not an easy thing for him to take on. This was not an easy assignment. It was not an easy role to assume, but he found a way to navigate an incredibly complicated situation and came out of it with many sides a lot better for it."

'Let's go' to Ireland

In 2020, Rupert told the Times that his involvement with Ireland began in Florida in 1992 when he was living in the city of Treasure Island, a barrier island in the Gulf of Mexico. He began a trucking business there.

"I was on the other side of my second wife and I was in Florida and ran into a woman," Rupert said. "She was from Massena, but she lived down there."

The woman, he said, was of Irish descent and they frequented a bar on St. Pete Beach, a resort city set on a barrier island, west of St. Petersburg. An Irish pub was located on the island and the pair commented to each other how they liked the music played there.

"We were drinking one day and she wanted to go to Ireland," Rupert told the Times in 2020. "I said, 'Sounds OK to me. Let's go.' So we did."

He fell in love with the country.

"It was like going back to Madrid or Waddington in the 1950s," Rupert said. "Ireland progressed a lot in a very short period of time, but in the early '90s, it was still like the 1950s."

A visit from the FBI

In 1992, Rupert moved on to the Chicago area, where he set up a trucking company at Calumet Truck Plaza. He opened the business with his last $1,100 after his Massena-based trucking company filed for bankruptcy. Two years later, an FBI agent arrived at his doorstep, asking about his ties to Ireland, and especially with Joe O'Neill, a hard-line Republican who ran a pub in Bundoran and a realty office in Ballyshannon. He died in 2013, with thousands attending his funeral. The Irish Examiner called him "one of the founding members of Provisional Sinn Féin" and a "towering figure of Irish republicanism."

Rupert told the FBI agent that he and O'Neill were friends who discussed history. Rupert was a student of history, thanks to Madrid-Waddington's history/social studies teacher Edith Finnegan, who retired in 1978 and died in 2004 at the age of 87.

"So, the bigger story of all of this is being both not Irish, not Catholic, I managed to quite literally stumble into such a position in Irish history," Rupert said in his recent email. "The only Irish influence I had was Edith Finnegan, the high school history teacher at MWCS who was very Irish — mentioning the Irish situation on more than one occasion. But with me, her bigger gift was teaching me to love history. At 15 or 16, living in Madrid, working on a farm — short of going to war, what kid could imagine living this type of history?"

Rupert's meeting in Chicago with the FBI agent eventually led to Rupert being recruited for his undercover role. He began doing that in October 1994. To assist in his undercover operations, the FBI set Rupert up with a pub in the village of Tullaghan, County Leitrim. It came with an adjoining trailer park frequented by vacationing Irish Republicans.

He would testify later in Dublin, at McKevitt's trial: "From my moral teachings, I found it morally acceptable to do."

He would conclude his undercover work on Jan. 8, 2001.

The 'depth' and 'complication'

"Part of the way we want to tell these stories through Entropy and the 'Underbelly' series is getting into that depth and complication and explaining the sort of worlds that these people, and occasionally, FBI agents find themselves in," Main said. "We found ourselves building out a road map of how we would tell the story and we wanted to add the details, the history. Not only the history of the Irish conflict but also the history of Dave himself, because so much of what made him good at doing this is a lot of the story of his background, his upbringing and adult life. So, as we mapped it out, we just found ourselves thinking, 'We think people are going to want more — more detail, more history, more backstory so that's how we ended up in a 12-episode series."

Rupert is the youngest of seven children of the late Donald and Emma D. Rupert. David's father died when he was 14.

"My mother was the daughter of a poor sharecropper from Rossie," he noted in his email. "She made it through eighth grade, which you had to then go to Morristown to High School and that was too much of a step and she was needed at home."

"She was born in 1914 and her father, who was as instrumental in my life as my own father, was born in 1881," he said. "In any case short on education, long on wisdom, she wanted me to know not to be a mouse, not to accept the status quo."

His father was born in Canada in 1907 "making him British," Rupert said. "All I remember about the Irish was him telling me to wear orange on St. Patrick's Day, and of course they were Catholic. What I remember about Catholicism was my mother saying about my older sister who married a Catholic fellow from Waddington: "'Your grandfather would roll over in his grave if he knew this.'"

Rupert said he would love to visit Ireland again, and even live there. "But I understand, my actions were an unforgivable transgression to many, so probably not in this lifetime."

'A wild ride'

Rupert said that after the release of "The Accidental Spy," three movie studios were working together preparing a "combined, single offer" to tell the story of the book, with an 18-month option. The COVID-19 pandemic and various disputes ended that project, he said.

"A movie deal is not dead, but I can't elaborate on it at this time," he said.

"Underbelly: The Rebel Kind" podcast also helps to unravel "The Troubles" — the decades-long conflict in Northern Ireland and the shadows it cast. The podcast explores the last impact of such a long and torturous conflict on the people of Ireland and Northern Ireland, along with the Irish-American identity.

"Dave's story, his daring, is a remarkable and I'd say critical bookend to the decades of modern violent conflict in Ireland between nationalists and unionists," Herguth said in a news release.

"No one suspected the Chicago trucker mopping the floor of his pub on the Northern Ireland border was the most successful spy in the history of 'The Troubles' and would help save the peace process," Pallasch said. "This is a wild ride that will keep you tuning in every week."

"You always want to remember, 'One man's terrorist is another man's freedom fighter,'" Rupert said. "So, the side you take in a conflict may not be right or wrong. The problem though, is weapons become more destructive and one bad actor can kill so many. Humans need to take a stance to stop the killing. If I did one good thing in my life, I was instrumental in stopping the killing in Ireland. I point to 26 years of peace dividends in that society as proof."

The details

n WHAT: The podcast series "Underbelly: The Rebel Kind," produced by Entropy Media.

n THE TOPIC: Madrid native David Rupert: "The real-life adventure of a Chicago trucker-turned-spy who took down a violent faction of the IRA."

n EPISODES: The 12-part series premiered March 13, with episodes being released weekly. Thus far, the episodes: Episode 1: "There once was a trucker from Chicago." 2: "A Little Off Base." 3: "The FBI Walks Into a Bar." 4: "It's a Funny Place, Tullaghan." 5: "Coin Operated."

n WHERE AVAILABLE: On all podcast platforms.