The Spy Who - The Spy Who Jailed the Omagh Bomb Plotter | Friend, Foe or Fortune Hunter? | 1

Episode Date: January 6, 2026

After years of violence, peace is within reach in Northern Ireland. But then a mystery American is seen with IRA hardliners. But is he a friend, foe, or fortune hunter?See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wonderry plus subscribers can binge full seasons of the Spy Who early and add free on Apple Podcasts or the Wondry app. In an unmarked car parked opposite a hotel, a man sits with a camera concealed beneath his jacket. He's from Special Branch, the Irish Police Division tasked with counter-terrorism, and today he's carrying out surveillance on a 60-something town councillor. Joe O'Neill, what are you up to now? O'Neill is a hardline Republican. Republican. He's linked to a small paramilitary group known as the continuity IRA. It's 25 years

since the conflict known as the Troubles began. The fight is led by the provisional IRA, which aims to get the British out of Northern Ireland and reunite the province with the Republic in the south. So far, more than 3,000 people have died and tens of thousands have been injured. But while the provisional IRA is the main force fighting British rule in Northern Ireland, dissident Republican groups, like the continuity IRA, also pose a threat. The surveillance officer shifts his position, trying to get a clear shot of the man O'Neill is chatting with. He's tall, maybe six foot seven, solid, broad-shouldered, and thick set.

Noticable. And who's this big fella? The officer opens the window an inch, enough to catch snatches of conversation and a distinct American accent. So, you're a yank. The officer takes a snapshot of the two men shaking hands, smiling. Then the giant American turns and goes into the hotel. O'Neill walks a few yards to where his old battered Mercedes is parked. He stops.

and looks around. The officer shrinks down in his seat. O'Neill hasn't spotted him. The officer relaxes, starts up his car, and heads in the direction of Sligo police station. He needs to get these photos developed and to Dublin as soon as possible. O'Neill and his men are well known to Special Branch,

But the American is new, and that probably spells trouble. A few hours later, Special Branch Headquarters, Dublin. A group of officers sit around a large desk cluttered with folders and half-drunk cups of tea. An inspector spreads out the photos of O'Neill, and the mystery America. American. We just got these in from Sligo. Joe O'Neill conducting some kind of business with an unknown male. Do we know anything more about the guy? The Snapper says he's American. The special branch officers fall silent. This is serious. They do know this. Irish Republican groups are getting money and weapons from sympathizers in America. Every dollar, every bullet, keeps the

conflict alive. Until now, the continuity IRA has been a side-show, a paramilitary group that's all talk, no action. But if it's now got back as in America, it might be about to go operational. This unknown American is now a terror suspect. And guilty or not, his life is about to be turned upside down. From Wondery, I'm Braza Jaffrey, and this is The Spy Who. Beneath the veneer of the everyday lurks the realm of the spy. It's a dank, murky world, full of dark corners, sinister motives, and corrupted morals, a place of paranoia and infiltration, sabotage and manipulation. In this series, we're going back to the final years of the Northern Ireland conflict,

also known as the Troubles. After nearly 30 years of violence, the Provisional IRA and the British government are edging towards a peace settlement. But when hardline Irish Republicans vow to keep fighting for a United Island, an unlikely spy will emerge to help take down the latest threat

to peace in Northern Ireland. What you're about to hear are dramatised reconstructions of events, based on the information that's been made public, But remember, in the shadowy realm of the spy, the full story is rarely clear. You're listening to The Spy Who Jail the Omar Bomb Blotter. This is episode one, friend, foe, or fortune hunter. It's July 1994, and on the outskirts of Chicago, David Rupert is in his upstairs office,

overlooking Calumet Truck Plaza. The plaza is a self-contained town for long-haul truckers, complete with 22 fuel pumps, a diner, tattooist, motel, and a massage parlour. Rupert eases himself out of his chair. and closes the window to block out the rumble of trucks. He's a six-foot-seven, heavyset trucker with grey hair. Invoices and final demands lay scattered across his desk. Rupert's 43, and his life, and business, are unravelling.

He has three marriages behind him, and owes more than half a million dollars in unpaid taxes. As he contemplates a bit of creative accountancy, there's a knock at the door, And a man walks in. David Rupert? The man flashes a badge. Agent Buckley, FBI.

The man sits without waiting to be asked. In the past, Rupert's found ways to make his taxes disappear. He fears the FBI have finally caught up with him. He smiles at the FBI man. How can I help you? Buckley, Pulled some photos from an envelope. Recognize these?

Rupert looks at the photographs of himself in Ireland. Outside a hotel in Sligo with Joe O'Neill. Rupert relaxes. Whatever this is, it's not about his more unorthodox business activities. Sure. Ask me on vacation in Ireland. Say goodbye to a friend. And how do you know this friend?

through a redhead of men in a bar. Two years earlier, Rupert dated a Chicago-based lobbyist for Irish Northern Aid, an American organisation that supports the idea of a united Ireland through peaceful means. We went on holiday. He introduced me to some of her Irish friends. You still in touch with her? No. We barely lasted a few weeks.

But I got a taste for Ireland and I've been back a few times. since. I didn't know the FBI were taking holiday snaps for me. This is serious. That man you're in the picture with is a member of the IRA. So what? Doesn't make him a bad person. And he runs a great pub.

Buckley leans over the desk. Like I said, your pal O'Neill is involved with the IRA. If you want to stay out of trouble, it might be a good idea to tell us anything you know about what he's up to. I don't know. anything. Joe's into politics and he'd like the Brits out of Ireland. Show me an Irishman who thinks

otherwise. Think about it. Buckley takes out his business card and hands it to Rupert. Think about it carefully. I'll be back. Rupert listens as Buckley's footsteps disappear and then he picks up the phone and dials O'Neill's number. Joe, it's David Rupert. Yeah, yeah. Listen, I just had a visit from the FBI. A month later, Bunduran, County Donegore, a few miles from the border with Northern Ireland. Inside Joe O'Neill's pub, Maureen,

Brennan taps her feet to the music and looks at the IRA posters that blasts to the walls. Maureen's a slim brunette from Dalton, Illinois, and she's on holiday with her new boyfriend, David Rupert. They met at the Trucking Plaza, where she works as a manager. Her mother was second-generation Irish, and she's always dreamed of going to Ireland. But work, and raising her daughter, Dory, on her own, meant travel was never an option. I can't quite believe I'm here, David. It's a dream come true. It is a great place.

I knew you'd love it, Maureen. I'm just going to the restroom. Maureen looks at the pub's owner, Joe O'Neill. But he's too caught up in conversation with another man to notice her. From where she's sitting, she catches the odd snatch of what's being said. I reckon they're actually going to declare a feckin ceasefire. starting to look that way. The progress are selling out. You're from my dead body.

What we need is a continuity Irish bombing campaign. Show them we'll never give up. Maureen, stiffens. She's not naive. Her mother often talked about the terrible injustices the Irish have suffered at the hands of the British, and she knows about the armed struggle. But she didn't think the people in this pub looked like the kind of people who would be involved in it. She sips her drink, frowning, as David returns.

All okay? I just love this pub. And Joe's a character. You like him, don't you? I do, but... Mots up? Who's that he's talking to? She nods to the balding man with a greying beard.

Him? Oh, that's Mickey Donnelly. I heard him talking about a bomb campaign. You need to understand, Maury. he's one of what they call hooded men arrested by the Brits locked up without trial and tortured easy to understand why he's not in a hurry

to forgive them but talking about bombings at a bar David I'm used to working around truckers and how our men talk but it all seems a bit out of place to be honest that's what I thought the first time I came here

but I've talked to Joe a lot about the situation and I'm not saying he's right going around killing people but I think I understand why people here feel they can justify it that's just what it's like in Ireland the following his office. The following month, Chicago inside his office at Calumet's truck plaza David Rupert sifts through more bills and tax demands

his recent holiday in Ireland already feels like a distant memory Rupert looks up he's not expecting anyone who is it without answering in walks FBI agent Buckley afternoon David

might have I come in? Seems like you already have. Might have I sit down? Seems like you already are. Listen, I'm afraid we got off on the wrong foot last time and I'm sorry if I gave the impression that we thought you might be mixed up in anything. I'm not.

We know. And that's why I'm here. To apologize? Or is there something else? Let me explain. There's a real chance of achieving peace in Northern Ireland. And President Clinton is putting his weight behind it. The provisional IRA have announced a ceasefire, but the question is,

will it hold? Or will splinter groups like the continuity IRA keep on fighting? You think I know the answer? I think you could help us find the answer. Buckley, eyes the receipts on Rupert's desk. You love Ireland, yeah? So what if we pay for your trips? All you've got to do is tell us what you see. and what you hear. So, you're saying, I just travel. Stay in touch with friends. And the FBI foots the bill. That's right.

Rupert thinks for a moment. It's tempting. He looks out of the window and watches a truck rolling in. This is the life he knows, but it doesn't amount to much. Ireland is where he feels most at home now. I'll think about it. But I need to tell Maureen my girlfriend Who's funding the trips

We're planning to marry and I've had three marriages already We're going to start this one by lying to her Later that evening Rupert's house just south of Chicago Rupert and Maureen sit together on the couch Watching a police drama on the TV Maureen is relaxed, but Rupert is uneasy. Maureen, there's something I need to discuss.

He tells her about the FBI visits, and the offer, Buckley, made that afternoon. Maureen switches the television off. The FBI, following you? Wanting to pay for our trips? Jesus, David, is this stuff you know you haven't been telling me? No, no, I swear to go. God, that's the thing. Joe O'Neill tells me stuff about the IRA, but he just wants me to understand the situation better.

If he knows anything about their operations, he's never let on to me. But if the FBI wants to pay for our trips to Ireland, why not take them up on that offer? And if we do find out more, then perhaps we can get more money from it. I don't know. I heard these people talking about bombs. Is it worth the risk just for free trips to Ireland? I've got a daughter. I don't want to get into any trouble. You know, Maureen. I love you

and I'm going to tell you something I've never told anyone before sometimes I look at my life and I see three failed marriages and a load of debts and want my next marriage to last for life and I want to do something more with my life what do you mean

I don't believe it's right to kill people so yes it's a risk but we'll be paid for taking that risk this could be the way out of the mess I'm in and what if we could actually do something that might help stop the bombs Rupert looks at Maureen. It reaches out, takes his hand, and squeezes it.

It's the answer he hoped for. They are in this together. Chicago. It's more than two years since the FBI recruited David Rupert, and he's now a fully fledged spy. The FBI pay him $2,500 a month to pose as a successful haulier to his Irish pals. His debt-ridden trucking business is now his cover. He and Maureen have married, and with her Irish roots and his contacts in Ireland, they've managed to get close to Chicago's Irish community. And today, Rupert's attending an Irish Republican fundraiser in a local school hall.

And the FBI wants to know what's going on behind the scenes. Five tickets for a dollar and the chance to win seats for the next Bears game. Rupert threads his way between cupcake stalls and raffle sellers. The fundraising is on behalf of the Irish Freedom Committee, which supports the families of IRA prisoners. A woman approaches the raffle cellar. I'll have 20 tickets. She smiles at Rupert. All in a good course.

Sure. Good luck. He heads over to a smart-suited octogenarian with a thin moustache who stood outside the school office. Hey Frank, you got a great turnout here. People are generous. We should do well today. Frank grew up in Northern Ireland in the 1930s. He faced trial himself for IRA membership before fleeing to Chicago, where he set up a bar.

Now he's also the chief organizer of these fundraisers for Irish Republican causes. David, come inside the office with me for a moment. I want to talk to you. Frank ushers Rupert into the adjoining room. He sits on the edge of a desk. and waves Rupert's into a chair. I was wondering, do you have another trip to Ireland planned anytime soon?

Nothing concrete, but business is doing well, and Maureen and I like to visit as often as we can. Is there anything you'd like me to do while I'm there? It's more of a case of what you might be able to take with you. Rupert senses what's coming. The parents in the hall outside believe they're raising money for families of IRA prisoners. But unbeknownst to them,

Frank secretly channels much of the funds to the continuity IRA, the paramilitary group that his friend Joe O'Neill belongs to. You're a friend of Joe O'Neill, aren't you? I'd like to think so, and I hope he thinks of me as a friend too. So what I'm saying is,

we're raising money here in Chicago, and Joe needs that money in Ireland. And perhaps there's a way of getting it to him, standing right in front of me. Sure. Whatever I can do to help. Rupert is delighted. Frank wants him to be the courier for the continuity IRA's gun money. And this should please his FBI bosses. It's the perfect cover for his spying activities in Ireland. And if he's the money man, then he's more likely to be trusted too. A few months later,

Bundoran, Ireland. Rupert is in the office above Joe O'Neill's pub. He and Maureen are back for another vacation. But this time, he and Maureen are staying in their new holiday home, which O'Neill helped them find. Are you all settled in now? Maureen likes the place? She does.

We both do. That's good. This area could do with more American tourists and I'm not just talking about the money they bring though that's welcome. No, it's the understanding that helps. The more people who visit and better understand the situation the better the chances of achieving our goals.

You know, Maureen and I both love this part of the world and you've really helped me understand the situation here, Joe. I'd like to do more if I can. If there's anything else I can do to help the move and just let me know. Well, there is something, as it happens. We need more than just cash from the States. We need supplies too.

We know where to get hold of them, and there's a teacher in Donna Gore, willing to receive parcels at her school. She'll see they reach me. We just need someone to mail the stuff. If we're talking bombards here, I'm happy to help, but is it safe to send them to a school?

What if one of the kids... No, don't worry. We've thought of that. Nothing's assembled. The detonating cords are contained in skipping ropes and the explosives will be hidden inside teddy bears. Rupert forces himself to nod and smile. He can't do anything illegal without the FBI's consent.

But the reality of what the people he's involved with are prepared to do hits him. He thinks of O'Neill as a friend and a man of faith. But he's also a man willing to smuggle. bomb parts through a playground filled with six and seven-year-olds. I'll see what I can do, Joe. I'll do whatever I can to make a difference. Two months later, Southampton, England. It's just after breakfast, and David Rupert is walking around the gardens of his hotel

with a man called Norman. Norman works for MI5, the British Security Service, which has our asked the FBI if they too might meet their man in Ireland. Norman's tall, almost the same height as Rupert, tall enough for Rupert to feel he can level with him. Norman, I want you to know that I'm fully aware that I got the MI5 potential informant room last night. I'm not sure I know what you mean.

I hope they gave you a good room. C-view and all that. C-view, but hot as a sauna. I didn't get any sleep. I'm guessing you rigged the heating. I know sleep deprivation is a great way to tell if someone is lying or not. I'm sorry you didn't sleep, but you're crediting us with rather more power than we have.

But there are a few things I'd like to go over with you. I'm still trying to understand how someone with no Irish ancestry ends up being asked to move bombarts for the continuity IRA. Rupert explains about the Irish scene in Chicago, the holiday with a girlfriend, and how he started spying for the FBI. And my five wants to make sure his story stands up. So Joe became a friend, and he taught me about Irish politics,

and I asked him if there was anything I could do to help. Norman seemed satisfied with the story. But then asks a question, Rupert didn't anticipate. And what would you say if we asked you to assassinate one of the continuity IRA? Well, I guess that would depend on how much you're willing to pay. I get a good salary from the FBI. No. No, we're not in the assassination business.

I'm just testing you. I'm glad to hear it. I won't kill anyone, but I do expect to get paid for the risks I take. My hope comes to the price tag. A few weeks later, Chicago. Rupert sits across a table from Norman, this time in an air-conditioned hotel room in downtown Chicago.

Norman pulls his jacket tighter around him. It's cold in here. Perfect temperature for me. I'm sorry if you're not comfortable. I could call reception, if you like. Don't worry. Do you need me to go through the details again? No need.

I got it. Rupert leans back and repeats the details of the conversation they've just had. My job is to go to Ireland as often as possible. Report back on the splits in the Republican movement. Who wants peace? Who wants war? Each trip, I'll meet with you. If I ever need the emergency line, I'll call and give the phrase,

it's a bit drizzly and drumcliff echo. I buy encryption software, install it on my laptop, and email my report straight to you. That's almost word for word. I let you into a personal secret. I had an astigmatism as a kid. I was slow to read, so I had to memorize all my textbooks. Comes in handy now.

Indeed. So, that's the job you're offering. But what's the pay? Norman sits back in his chair. We can offer you $50,000 a year, on top of what you already make with the FBI. Is that acceptable? I'll shake on that.

Rupert's now an official MI5 operative, planted among the most fanatical Republicans. His money's almost doubled, but if anyone finds out who he's working for, he'll be a marked man. December 1997. Four months after David Rupert agreed to spy for MI5. Falkara, County Donegal, Ireland.

A car pulls up outside a former Catholic boarding school and outsteps a small boarding man with glasses. He's Michael McEvitt, the former quartermaster of the Provisional IRA's Northern Command, the man who manages the terrorist group's supplies of weapons and equipment. With him is his wife, Bernadette Sands McEvitt, who's also the sister of martyed hunger striker, Bobby sounds. They head inside the building, following signs to an Irish language seminar. Officially, that's what the former schoolhouse has been booked for. Unofficially, it's the Provisional IRA's general convention, and McEvitt, who quit the

organisation two months earlier, is here to disrupt it. Well, wait a moment. He pauses outside the door. From inside, he can hear Martin McGuinness addressing the room. McGinnis is a member of the provisional IRA's army council and deputy leader of its political wing, Sinn Féin. After almost 30 years of violence, it's become clear to many Republicans and the British government

that neither side can win this fight. So now, the Provisional IRA is ready to suspend its military campaign to enable peace talks with the British to take place. There is widespread support for this within the Provisional IRA, but McEvitt is vehemently opposed. Christ Almighty. Has he forgotten who controls the keys to the gunrooms? Right. We're going in.

The room falls silent as the McEvitz enter. Everyone here knows they're dead set against making a deal with the British. Having made an entrance, McEvitt waits for his turn to speak. I think it's clear what's going on here. The Army Executive is giving up on everything we have fought for, but there are those of us who will continue to fight until we have a United Island. Many people in the room support the ceasefire, but there are plenty who agree with McEvitt too. After making his point, McEvitt walks out, along with his wife and

several other IRA hardliners. Once outside the hall, he turns to speak to them. I take it all of you follow me because you are willing to continue the fight for justice. Of course. Absolutely. Right. Good. Because I'm still in control of the IRA weapons caches, so from now on we work together as the real IRA. The provisionals are yesterday's men. We're the future. We're the ones who are going to win this war.

Two months later, Moira, County Down, Northern Ireland. Just after 11 p.m. A small car eases into a roadside bay outside the Royal Ulster Constabulary Police Station. The man at the wheel sits very still for a moment, fingers tight on the steering wheel. He's a member of McEvitt's new splinter group, the real IRA. He checks the police station's facade and turns off the engine. He walks down the street to a waiting saloon car and gets into the passenger seat. The car is driven by a member of the continuity IRA, and tonight, these two men are staging one of a series of planned joint operations between the two hardline Republican groups.

They stop a few blocks from the station alongside a public phone box. The real IRA man gets out, walks, walks over, and takes a handful of coins from his pocket. He lifts the receiver, does. stars the number of the Mays prison in Belfast. This is the real Irish Republican Army. A device has been placed outside the Moira police station. Detonation in 10 minutes. Later that evening, Bundoran, Republic of Ireland.

McEvitt is at home, watching the evening news with his wife, Bernadette and several real IRA lieutenants. Listen up. He shushes them as news of a bomb at the Moira police station is announced. Eleven people have been injured, including seven police officers. The men in McKevitt's home, cheer. Aided by the continuity IRA, the real IRAs just carried out its first successful operation

and sent a message to Britain that the armed struggle isn't over. Two months later, Belfast, Northern Ireland. Outside Stormont, the Northern Ireland Assembly building, the world's media waits. A TV news reporter checks his watch.

Inside the building, representatives from Northern Ireland, the Republic of Ireland, Britain and America, are hammering out a peace deal. The deadline for reaching a deal was midnight, It's now late afternoon and there's still no word. The TV reporter and his cameraman walks towards a mixed group of Catholics and Protestants holding a prayer vigil for peace.

Can I ask you a few questions? Why are you here? What are you praying for? I just hope they signed the deal. We need to move forward. We've had enough of the bombings. Everybody here is praying for peace. The reporter looks at his watch.

As each hour passes, so does the hope for an end to Northern Ireland's bloody war. Then, his cell phone rings. It's a colleague who's watching the negotiations from inside the building. He listens and turns to repeat what he's just been told to the people outside. They've done it. It's signed! The following day, the Republic of Ireland. David Rupert drives his rental car out of the town of Bondoran. Joe O'Neill in the passenger seat.

Rupert's agreed to give him a lift, but he doesn't know where he's going. Or why? So where are we headed, Joe? Is your Mercedes finally giving up the ghosts? There's a Kenny. I'll tell you when to turn. And no, the Merck's still breathing, but it's too recognisable. Ruper's hands tighten on the steering wheel.

The rest of the country is welcoming the signing of the Good Friday Agreement and hoping that the troubles are finally over. But O'Neill is in no mood for celebration. Whenever they pass a police car, O'Neill lifts his hand to half cover his beard. He clearly doesn't want to be recognized. What's all this about, Joe? We're scouting for roadblocks.

McEvitt is planning a response to the Good Friday Agreement. I'll assume you're not talking about speeches here. No, lad. I'm talking about using a rocket launcher to blast the police land rover on the other side of the border. Rupert nods. As if in agreement, but his stomach lurches. The ink is not yet dry on the peace deal, and the hardliners are already planning more bloodshed.

We need to act today while the media's attention is still focused on Northern Ireland. if we leave it too late this will be just another attack if we do it within 24 hours at the deal it will show what they agreed means nothing Rupert keeps his eyes on the road they are now at the border with Northern Ireland

and they've not passed a single police checkpoint O'Neill visibly relaxes no checkpoints means little chance of the operation being foiled right that's us roads look clear enough head back now

Rupert drives back O'Neill then parks a few streets away and uses a phone box to call the emergency number given to him by MI5 He needs to alert them to O'Neill's latest plot. The next day, Bondoran. In the graveyard behind the church, Joe O'Neill stands by the grave of an old paramilitary comrade.

He looks up on hearing someone approaching. It's Mickey Donnelly, the man he's been waiting for. Donnelly was one of the original members of the members of the British. provisional IRA. He defected to O'Neill's continuity IRA when the provisional's took the first steps on the road to peace. And the look on his face is anything but peaceful now. What the hell happened yesterday? You said you checked the road. I did. drove it myself there and back. It was completely clear that. There were guard her everywhere this morning. So we couldn't move the

rocket launcher. Someone must have spotted you. Your car stands out a mile. I didn't kid, I'm not stupid. David drove me in his eye car, or McCavitt's furious. He wanted to attack while the press were still in Belfast. We've missed that chance now. Maybe they anticipated the move and put in patrols as a precaution. No, it's too much of a coincidence. Either you got spotted or somebody's tipped them off. There's a spy. I'm sure of it. The two men stare at the gravestone of the IRA man, contemplating these latest nails in the coffin of the Republican movement, Their former commander has signed up for peace, and the numbers of those willing to continue the fight are dwindling. If there is a traitor in their midst, they need to root out whoever that is, before their war for a United Island is completely lost.

Wondery Plus subscribers can binge full seasons of the Spy Who early and add free on Apple Podcasts or the Wondery app. Have you got a spy story you'd like us to tell? Email your ideas to the spy who at Wondery.com. From Wondery, this is the first episode in our season, The Spy Who Jailed the Omar Bomb Plotter. A quick note about our dialogue. We can't know everything that was said or done behind closed doors, particularly far back in history.

But our scenes are written using the best available sources. So even if a scene or conversation has been recreated of a dramatic effect, it's still based on biographical research. We use many sources in our research for this season, including The Accidental Spy by Sean O'Driscoll. The Spy Who is hosted by me, Marza Jaffrey. Our show is produced by Vespucci, with writing and story editing by Yellow Ant for Wondery.

For Yellow Ant, this episode was written by Lizzie Enfield and researched by Louise Byrne. Our managing producer is Jay Priest. For Vespucci, our senior producer is Ashley Clivery. Our sound designer is Alex Port Felix. Natalia Rodriguez is the supervising producer. Music supervisor is Scott Velasquez for Frisson Sink. Executive producers for Vespucci are Johnny Galvin and Daniel Turkin.

Executive Producer for Yellow Ant is Tristan Donovan. Executive producers for Wondery are Estelle Doyle, Theodora Laudis and Marshall Louis.