The wild, true story of a Chicago trucker-turned-spy who infiltrated the Real IRA
Did you hear the FBI paid to lease a pub on the Irish side of the Northern Ireland border for its amateur spy, trucker Dave Rupert, to make inroads with IRA supporters?
The FBI is the United States’ domestic intelligence agency – not the CIA – working with Britain’s domestic intelligence agency – MI5, not MI6 – operating in a third country, the Republic of Ireland, with only minimum notice to Ireland’s government.
This unorthodox operation – skirting all the rules – was run by a maverick FBI agent, Ed Buckley, whose charge was to investigate the flow of guns and money from Chicago to the IRA.
Who’d have bet that Mickey McKevitt, the leader of the IRA’s most militant offshoot, the “Real IRA,” with his lifetime experience sniffing out British spies, would be taken in by a 6’7” protestant trucker with no ties to Ireland?
And yet, the crazy scheme worked.
“They’ve been chasing him for 25 years, and really never got anybody close to him, and, here I walk in and, you know, ‘Hi, how ya doin’?’” Rupert reveals in the podcast by veteran journalists Bob Herguth and Abdon Pallasch whose 12-episode, Underbelly: The Rebel Kind, released by L.A.-based Entropy Media, captures the story of Rupert’s recruitment by the FBI to infiltrate the IRA splinter groups who were opposed to the Good Friday Agreement.
Pallasch explains: “In fine Chicago tradition, Rupert made himself the bagman, bringing funds raised by American support groups for IRA prisoners over to Ireland. Showing up in Ireland with envelopes full of American cash opened doors to help Rupert ascend the ranks of the IRA splinter groups there.”
Throughout the 12 episodes, we learn that during Rupert’s seven-year ordeal, he would stumble, Forrest Gump-like, into history. For instance, the time he was trying to impress some Real IRA supporters in Chicago and got himself named webmaster for a candidate for governor, only to crash that candidate’s website.
And then there’s the time that Mickey McKevitt sent Rupert to El Paso, Texas, to scout the border, camcorder in hand, with an eye toward smuggling weapons across the border into Mexico and on to Ireland – or to smuggle McKevitt from Mexico into the U.S.
That was in 2000 after Texas Gov. George W. Bush had locked up the Republican nomination for president and dispatched his wife to El Paso to the same hotel Rupert was staying at. Rupert asked the future first lady’s security detail if they were there for him. No, the puzzled security guards told him – they were there for the first lady.
Rupert’s colorful background – his multiple bankruptcies and divorces; his stories of the road as a trucker – helped him convince McKevitt and his crew that he was a law-breaking smuggler like they were, even if he weren’t Irish or Catholic.
“If you brought this to some Hollywood studio and they were going to make a movie – and it’s a truthful movie – here’s what’s going to happen: They would’ve shown you the door right away and said, ‘This is bullshit! Nobody’s gone to believe a word of this! This is nonsense!” said Andy Wilson, a professor of Irish history at Loyola University of Chicago.
“Dave Rupert is about as far from a dashing James Bond as a spy could be,” Pallasch allows. “Have you ever seen James Bond scrubbing vomit off a pub floor or changing out Guinness kegs? But that unglamorousness of Rupert’s assignment may be precisely what gave him credibility in the eyes of the folks he was sent to infiltrate.”
As well as retracing Rupert’s path through Ireland; New York, Texas, Florida, and Chicago; interviewing the characters he interacted with, and offering a sometimes comic, and definitely eye-opening window into the conflict in the North of Ireland, Pallasch said that he and Herguth also tried to break new ground in the Rupert story, asking for instance, “Why did the FBI suddenly develop an interest in Northern Ireland?”
“Because the U.S. Government wanted the U.K.’s intel on Islamic terrorists in the Middle East. And MI5/MI6 thought it fair to ask for the FBI’s help with IRA supporters in return. And why was the FBI’s IRA guy in Chicago, Ed Buckley, so motivated to recruit Dave Rupert as a spy? Because Buckley’s first attempts to infiltrate the IRA’s U.S. support networks were disasters. He needed a win.”
As reporters for the Chicago Sun-Times and Irish America magazine, Pallasch and his colleague, Bob Herguth, had both written about Irish and Irish-American issues. Starting in 2001, they began tape-recording interviews with Dave Rupert in which he explained the unlikely events that put him on a path to international espionage for the FBI and MI5.
Those tapes would eventually become the subject of a federal court case, which the journalists get to in Episode 11. But they have never been played publicly before this podcast.
“I probably don’t disagree with the Republican philosophy that the Brits probably shouldn’t be there,” Rupert admits.
Listen to the podcast and you can learn how – and why – he did it.
New episodes of the podcast are released every Wednesday. So far nine intriguing episodes have been released and episode 10 is due to be released on Wednesday, May 22nd.
To hear Underbelly: The Rebel Kind listen on your favorite podcast network or visit Entropy Media. ♦
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