A spy walks into a bar … and saves the Irish Peace Process... An upstate trucker’s unlikely path to international espionage ran through the Irish pubs of New York, Boston & Chicago.

by Abdon Pallasch Copyright ©2026 All rights reserved by the author

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Amid all the big talkers haunting New York’s Irish pubs, belting out new ways to drive the Brits from Northern Ireland, Dave Rupert stood in a class of his own. His sheer size, for one thing. When you’re 6’7” and 300 lbs., stealthiness comes awkwardly. But Rupert pulled his cap on and sank into a chair at Molly Wee’s on 8th Avenue near Madison Square Garden, trying to look inconspicuous. You'd be surprised how well he does it. Rupert wasn’t Irish or Catholic. In his youth, far upstate on the Canadian border, Rupert’s dad would dress him in protestant orange for St. Patrick’s Day. Rupert, 48, came straight out of Central Casting as a mole infiltrating the Irish Republican Army, so the most head-scratching part of this story remains how many seasoned IRA leaders fell for his pitch.

Martin Galvin, publicity director for Irish Northern Aid (“Noraid”), was one of the most recognizable faces of IRA support in the United States. The British banned him from Northern Ireland. And Galvin was completely on board with Rupert as he walked into Molly Wee’s that night in November of 1999. Taking the seat opposite Rupert at the pub, Galvin told Rupert it was great to see him again, and arrangements were all made for Rupert’s trip to Ireland the following Sunday. Just check into the Fairways Hotel in Dundalk, “Call them from the parking lot, and they’ll come collect you,” Galvin told Rupert.

Rupert was playing a very dangerous game, working his way up to the leaders of the most violent IRA splinter groups who were fighting against an Irish peace process the militants saw as a sellout to the Brits. A chasm had widened within the IRA. Most of the fighters in the Provisional IRA, “The Provos,” followed Gerry Adams and Martin McGuinness into the Peace Process to lay down their arms and pursue a political path to Irish empowerment through the Sinn Féin party. But the “hard men” who wanted to keep setting off bombs to drive out the Brits splintered off into groups like the “Continuity IRA” – which Rupert had been infiltrating for years – and the even more militant “Real IRA” led by Mickey McKevitt, which Rupert had recently crossed over to.

Molly Wee’s owner, Angela Reilly, a Northern Ireland native, walked over and sat down next to Rupert. She urged him to meet with her brother, Colm Murphy, when he was in Ireland. Murphy was a top deputy to McKevitt in the Real IRA and would eventually be the only one convicted for setting off a deadly bomb in the small town of Omagh that killed 31, mostly women and children, in the most deadly single attack of the Northern Ireland conflict. That conviction was later thrown out, though Murphy served time in both the U.S. and Ireland for attempted gun-running and other charges. Rupert, Galvin, and Reilly talked about a recent police raid on an IRA training camp. Rupert asked Galvin how much damage the raid did to the cause. Galvin told him it was not too devastating, Rupert recalled.

Rupert had learned over the years to be a good listener and to come across as very non-threatening. It was kind of a defense mechanism, given his size. He did not want to startle people or set off any alarms. He was a gifted schmoozer and salesman. It’s how he stumbled into the spy business to begin with. When the FBI came knocking at the door of his trucking business in Chicago, he worried they might be there for the $750,000 in unpaid taxes from his former business ventures. When they slapped down photos of him drinking with IRA-involved Irish pub-owners, he was actually relieved. Rupert knew he had only smiled politely when his drinking buddies told him of their efforts to drive the British from Northern Ireland. He never realized he’d become something of a local folk hero when he told them, “The problem is you’re not sending home enough body bags to England. That’s how the Vietnamese won the war – the body count, you know?”

Talking about his upcoming trip to Ireland, Rupert told Galvin he wanted to carefully explain to Real IRA leader Mickie McKevitt the idiosyncrasies of Frank O’Neill, the patriarch of Chicago IRA supporters, whom Rupert had guided over to McKevitt’s side. Frank O’Neill was a beloved pub owner in Chicago who served time for IRA-related crimes in Ireland. He would bring most of the Chicago supporters with him from Continuity IRA to McKevitt’s new group. “I’ve got Frank 100 percent on board” for the switch to the Real IRA, Rupert assured Galvin, who Rupert said was happy to hear it.

Rupert was traversing the Irish pubs of New York, Chicago, and Boston, trying to pull off “The Switch.” Do you remember the classic 1995 Seinfeld episode “The Switch,” in which Jerry Seinfeld tried to “trade up” from his ho-hum girlfriend, Sandy, to her sexier roommate, Laura, who had a lilting, feminine laugh? “The Switch? Can’t be done!” George Costanza chastised Jerry at their Upper West Side diner. “Do you realize in the entire history of Western civilization, no one has successfully accomplished the roommate switch?!” Just four years later, in 1999, Rupert, working undercover for the FBI and Britain’s MI5, was walking these same Manhattan streets, trying to pull off a very different switch – one he hoped could help cement his budding relationship with Mickie McKevitt, Britain’s top target in Ireland.

The Irish, British, and U.S. governments believed money raised by IRA supporters in these Irish-American pubs financed bombs like the one McKevitt’s group set off in Omagh, Northern Ireland, two years earlier, killing 31 people, including a woman pregnant with twins. The British government is conducting a long-sought inquiry into whether officials ignored warnings about the Omagh bombing that could have prevented it. When Rupert first met McKevitt, the Real IRA leader told him that his group was 20% responsible for the Omagh bomb disaster – they stole the car and built the bomb – but that Continuity was 80% responsible because they drove the car into Omagh and parked it in the wrong spot, where police were pushing people to supposed safety.

Rupert had first burrowed his way into Continuity IRA, a tad less militant than the Real IRA, run by aging IRA stalwarts. Rupert found that it was more talk than action. In the beginning, Rupert even convinced the FBI to use your tax money to lease him a pub on the Northern Ireland border for him to ingratiate himself with IRA supporters. Infiltrating the IRA is deadly serious business, but running a pub patronized by heaving-drinking IRA supporters was downright comical. Far from the suave image of James Bond, Rupert was the unglamorous spy mopping up vomit on the pub floor and breaking up fights. Hearing the rebel songs and his new friends’ stories of centuries of British treachery against the Irish, Rupert could not help going a bit native at times and telling his MI5 handlers one way to stop the violence would be for the Brits to leave Northern Ireland. “I probably don’t disagree with the [IRA supporters’] philosophy that the Brits probably shouldn’t be there,” Rupert said.

Rupert’s crazy pub scheme worked. The locals in Tullaghan and the IRA supporters from Northern Ireland who summered there came to see The Big Yank running The Drowes Inn as a supporter. Continuity stalwart Joe O’Neill (no relation to Frank) came to trust Rupert and introduce him to even bigger fish in the IRA pond. Against all odds, Rupert succeeded in trading up from the Continuity IRA to McKevitt’s “Real IRA.” McKevitt was quite literally trying to blow up the fledgling Irish Peace Process. Now Rupert’s job was to flip these American IRA supporters to McKevitt’s more dangerous group.

Few people outside of Rupert himself ever thought he could pull this all off. Not the Irish police, who thought little of Rupert and were mostly kept in the dark by the Brits and the Americans running this stealth operation on Irish soil. Rupert had no formal spy training. He was a 48-year-old trucker and a three-times-bankrupt wanna-be entrepreneur from far Upstate New York who left behind a string of failed businesses, angry creditors, and bitter ex-fathers-in-law. Rupert’s older sisters and brothers called him “Jobi,” short for “Joe Beef.” A big kid whose rollicking life had always fallen a bit short of his big ambitions. He was a protestant with no Irish ancestry – the kind of obvious mole that cunning IRA leaders like Mickey McKevitt spent their lives sniffing out. But Rupert was a good talker, practiced in the art of bluffing.

Posing as a wealthy American businessman available to bring envelopes of American cash raised by American IRA supporters over to IRA support groups in Ireland, Rupert made himself popular on both sides of the Atlantic. “Everybody wants to know the bagman because you’ve got the money,” Rupert said. “So we bought our way into their organization with their own money.” Rupert was risking his life every day he posed as a true believer in the cause, on his own, being driven to secret Real IRA army council meetings without his handlers in the FBI and MI5 having any idea where he was. "Dave Rupert was extremely brave and courageous, and thank God he escaped alive,” said Michael Gallagher, whose son Aidan was one of the 31 killed by the Real IRA’s car bomb in Omagh. “If they had had even a clue that he was passing on information to anybody, he would have been dissected. His body would never have been found.”

And yet somehow Rupert was pulling it off: “MI5 could not believe McKevitt was coming to see me. 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’?’" MI5 had been so skeptical that McKevitt would trust Rupert that they actively discouraged him in meetings and their nightly emails to him from making the switch from the older, more established Continuity IRA on Ireland’s West Coast to McKevitt’s wilder organization near the border town of Dundalk. But Rupert persuaded them to let him roll the dice.

Rupert had made switches before, including the kind of sex-driven “switches” Seinfeld focused on. Rupert divorced his second wife just to chase women. In a Florida Irish pub, Rupert met a beautiful redhead named Linda Vaughn. Vaughn was a powerhouse lobbyist, the reason you can’t smoke indoors in Florida. She brought Rupert to Ireland and introduced him to IRA-connected pub owners like Joe O’Neill, which led the FBI and MI5 to come knocking on the door of Rupert’s Chicago trucking operation. O’Neill and pub owner Vincie Murray in Sligo had taken a liking to Rupert because he walked in with their trusted friend Linda Vaughn on his arm. They schooled him on 800 years of British oppression of the Irish. They thought they had converted Rupert to their cause. But Rupert was just a survivor with a good poker face, and he took the FBI up on its offer to report back on what O’Neill and Murray were up to.

Mirroring the split in Ireland between IRA members who followed Adams and McGuinness into the Sinn Fein political party and those who stayed with McKevitt and the others still taking up arms, there was a corresponding schism in this country: Members of Irish Northern Aid “Noraid” – the main group collecting money from Irish-Americans to support the families of IRA prisoners in Ireland – splintered between the Friends of Sinn Fein which supported the peace process – and the Irish Freedom Committee which supported the militants.

Martin Galvin, a New York lawyer, was the public face of Noraid until the split. Galvin was the one who pinned down Bill Clinton in 1992 to promise that he would grant Gerry Adams a visa to the United States if elected president. That visa, issued over the objections of Britain and Clinton’s own State Department, is credited as a major impetus for jump-starting the Irish Peace Process, as recounted in the “NORAID: Irish America and the IRA” documentary released on the Irish television network RTE last year. Galvin recounted some of this history in the documentary, but he, the FBI, and MI5 all declined to comment for this story.

As Rupert and Galvin sat there at Molly Wee’s that night, they discussed the real tough nut they both wanted to crack: John McDonagh, the Irish-American host of Radio Free Eireann on WBAI community radio in New York. McDonagh sent two of his friends to Chicago a few months earlier to collect the money at a fundraiser there and bring it back to New York to hand over to their group in Ireland, allied with Continuity IRA. Rupert blocked that attempt, putting his considerable frame between McDonagh’s guys and the $20,000 collected at the Abbey Pub in Chicago. “They thought they were going to pick up the money,” Rupert recalls. “We said, ‘No.’ We sent them back to New York empty-handed.” Rupert would bring that envelope of cash to McKevitt instead.

Galvin told Rupert he was worried that McDonagh would blame Galvin for the Chicago crew’s switch to McKevitt and the Real IRA because of Galvin’s presence at the Chicago Abbey Pub event. “Well, I’m meeting with John McDonagh this evening, and I can tell him this doesn’t have anything to do with you,” Rupert assured Galvin. “I met McKevitt, and I liked what I saw, and he asked me to do a job and make all this happen, and so, if anything, this is my fault.”

Rupert got up, said his goodbyes to Galvin and Reilly, and strolled a few blocks and a world away to the Kevin St. James Bar, further up 8th Avenue. Owner Kevin O’Lunney was the son of Hugh O’Lunney, whose Times Square pub was a regular gathering spot for Rupert and his pro-IRA targets. Kevin St. James bar catered to a younger clientele. But it was an old war horse Rupert met there that night. John McDonagh may have spent summers on the family farm in County Donegal on Ireland’s northwest coast. But he speaks with a New York accent so thick you could slice it. In recent years, McDonagh used that voice as a “cabdivist” taxi driver, railing against the surge pricing he says gouges his cab profits. But 25 years ago, McDonagh deployed his considerable voice to rail against the “sell-out” Irish willing to cut deals with the Brits - on his still-running weekly “Radio Free Eireann” show on WBAI. McDonagh was very suspicious of the towering protestant with no Irish blood who professed such deep concern about British oppression of the Irish and spoke so openly about acquiring arms for the struggle.

“When he came to New York, he met with me at a couple of places, and he was telling me, ‘Yeah, I'm going to use the money to buy weapons,’” McDonagh recalls. “‘We have an army in the field.’ And I was like, looking at him. I didn't think he was FBI because I thought he was even too crazy. Now, I was in the American Army, right? This is crazy talk: ‘We're gonna arm an army in the field?!?’” The IRA supporters Rupert had been cozying up to in Ireland like Joe O’Neill would not even let the word “bomb” cross their lips, making a motion with their hands instead of saying the word – a caution against being caught on a mole’s tape. Rupert had no such inhibitions against loudly promising in these pubs to bring weapons to the IRA. It wasn’t like the FBI was going to arrest him. “I kept thinking: Who the fuck is this guy telling me that, ‘I need to get the money so I can buy equipment,’ and I'm looking at him, and I said: This guy is crazy,” McDonagh said. “I've been in the Republican movement most of my adult life. No one ever talked like he did.”

There weren’t many patrons at the Kevin St. James Bar that night, and both men recalled their argument grew louder as Rupert made the case for The Switch, and McDonagh said, No way – he was not abandoning the Continuity IRA, Republican Sinn Fein leader Ruari O’Braidaigh, and Rupert’s old friend Joe O’Neill. McDonagh had watched enough schisms over the years between Irish rebels and die-hards refusing compromise. The British learned over centuries to get the Irish fighting each other about which faction hates the Brits more for centuries of oppression. “I've been involved with the movement long enough to know there's always a ton of splits,” McDonagh said. “There's always a new organization that's coming up. ‘Oh, you're not hardcore enough.’ ‘You don't kill enough.’ There's always somebody or some group that's going to do more than what you're doing because, whatever organization you're with, it's never doing enough. And I've seen it all before.” McDonagh loudly and forcefully told Rupert in no uncertain terms that night that he was not splitting with the guys who brought him to the dance.

But at other pubs – at O’Lunney’s, Rocky Sullivan’s, Paddy Reilly’s, Rory Dolans, the Kinsale Club, McSorley's Old Ale House, Rupert met with and often closed the deal with American IRA dissident supporters. At a meeting at Connolly’s Pub on 47th Street, a compromise structure was approved for the Irish Freedom Committee, giving McDonagh a leadership position and naming Rupert’s Chicago colleague Deirdre Fennessey as secretary. Rupert helpfully volunteered to tape-record every IFC meeting so he could bring a copy back to Fennessy in Chicago, where she could type up the minutes. Rupert did not mention that he would be dropping a copy of the tape at the FBI’s Chicago office.

Why the FBI’s sudden interest in Northern Ireland? In 1983, 241 American service members were killed by suicide bombers in Beirut. The U.S. sought intelligence from Britain, which had an established network in the Middle East. In return, British authorities asked for U.S. help in stopping the flow of money and support from Irish-Americans to the IRA. The FBI tasked agent Ed Buckley with infiltrating IRA support networks. After a few spectacular blunders – including a mole who blew his cover – Buckley recruited Rupert, who delivered beyond anyone’s expectations.

Rupert’s chance encounter with Linda Vaughn and her IRA-involved friends had finally given him the opening to transform himself from an oversized underachiever to an actual international spy. Rupert worked his way up to becoming one of McKevitt’s most trusted right-hand men, taking McKevitt’s orders to bring money, weapons, and computer technology from the U.S. to Ireland. Rupert had to make excuses for the militants about why he couldn’t smuggle weapons on his flights from the U.S. to Ireland. Rupert got McKevitt to let his guard down. He told McKevitt he was a fellow smuggler, running truckloads of weed across the Mexican border. Rupert’s brother, Dale, was serving 10 months in a Florida prison for smuggling a ton of marijuana in a rig Rupert told McKevitt was his. McKevitt told Rupert he used to smuggle himself out of Ireland in the bed of a truck to get to Europe and Africa to buy weapons from former Libyan dictator Muammar Gaddafi.

Believing Rupert’s smuggling stories, McKevitt dispatched Rupert to El Paso, Texas, to scout options for smuggling weapons across the border through Mexico to Ireland – or smuggling McKevitt himself from Mexico into the U.S., even though McKevitt was on the State Department's suspected terrorist list. This was serious business with implications for both Ireland’s future and U.S. border security. Rupert succeeded in bringing the lion’s share of Irish-American dissident supporters over from Continuity IRA to the Real IRA, which won him even more admiration and trust from McKevitt. The envelopes of cash didn’t hurt either. McKevitt invited Rupert into secret army council meetings. He welcomed Rupert into his home to work on his computer, on which Rupert installed software supplied by MI5. Rupert and his wife, Maureen, went to dinner with McKevitt and his wife, Bernadette. “I liked him. He liked me. We'd probably be best of friends today had he not been a mass murderer and I not been a British agent,” Rupert quipped. 

The friendship came to an abrupt halt in 2001 when Irish police arrested McKevitt, charged him with directing terrorism, and announced Rupert would be the main witness against him. All those IRA supporters Rupert courted in Irish-American pubs turned on him. McDonagh blasted him as a “rat bastard” on his radio show. They hammered Rupert for all his bankruptcies, failed businesses, and divorces, and called him a criminal. During that time, my Chicago Sun-Times colleague Bob Herguth and I were meeting with Rupert in diners not unlike Monk’s on Seinfeld and recording Rupert’s recollections of his 7-year odyssey. The tapes nearly landed us in jail when we balked at handing them over to the FBI and McKevitt’s lawyers. Many of Rupert’s best stories from those tapes and interviews with some of the key players he interacted with can now be heard on our 12-episode podcast, The Rebel Kind, which won the Signal, Green Eyeshade, and Sunshine State journalism awards last year.

When Rupert took the stand against McKevitt in Dublin, McKevitt’s lawyers tried to hammer him with all those stories Rupert told McKevitt about his alleged illegal activity. What about his brother’s arrest, they asked. Rupert laughed and testified he had nothing to do with ¨ “I was sorry he got caught,” Rupert said. “He was 55 years old and should have known better.” McKevitt’s lawyers found no arrest records for Rupert. What about all the bankruptcies and divorces? They hammered him. What about all the failed trucking companies? “You’ve been a failure your whole life, haven’t you?” McKevitt’s lawyer pressed him. “I guess you’re right,” Rupert said. “But I was pretty good at this.” Rupert’s closeness to McKevitt helped convince the judges of Ireland’s Special Criminal Court to convict McKevitt of directing terrorism based on Rupert’s very detailed testimony about McKevitt’s operations. They sentenced McKevitt to 20 years in prison. The “Real IRA” crumbled without McKevitt’s leadership. The fragile Irish Peace Process has staggered forward and has transformed life in Northern Ireland over the past 25 years. If a majority of voters decide they want to reunify, Britain will let go, and both parts of the island can be “A Nation Once Again.”

A few final “switches:” Rupert switched up from lobbyist Linda Vaughn to his 4th and current wife of 30 years, Maureen, who proved a valuable asset in his spywork in Ireland. And he managed to transform himself from a sometimes-bankrupt trucker to a successful international spy who played a significant role in saving the Irish peace process. Rupert was quietly awarded the FBI’s highest civilian honor, the Louis E. Peters Award, in recognition of his success.McKevitt was released from prison after 15 years and died five years later of cancer. Most of the $10 million the American and British governments paid Rupert for his spy work over the years is gone. He lives a modest life somewhere in the United States, even driving an Uber for a while. He still looks over his shoulder for McKevitt sympathizers.

Former Chicago Sun-Times reporter Abdon Pallasch is co-host of the 12-episode podcast The Rebel Kind and communications director for the Illinois State Comptroller Susana Mendoza.

About the author: Abdon Pallasch worked as a reporter for the Chicago Sun-Times, The Chicago Tribune, and The Tampa Tribune, among other news outlets. He wrote the original stories that led to R. Kelly's federal convictions for exploiting young women. His podcast, Underbelly: The Rebel Kind, has won journalism awards around the country.