Mr. Wristwatch

Mr. Wristwatch

Truck driver, entrepreneur, womanizer - spy. Sophia Di Martino joins journalist Sean O'Driscoll to tell the story of one of the most unusual and effective moles in modern American history. When David Rupert met a woman in an Irish bar in Florida, the meeting sparked an unlikely chain of events that would lead him to infiltrate a deadly Irish Republican terrorist group on behalf of the FBI, MI5, and the Irish state - and put several key players behind bars. But the 'Big Yank' would pay a heavy price for his success.
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True Spies, Episode 188: Mr. Wristwatch

NARRATOR: This is True Spies, the podcast that takes you deep inside the greatest secret missions of all time. Week by week, you’ll hear the true stories behind the operations that have shaped the world we live in. You’ll meet the people who live life undercover. What do they know? What are their skills? And what would you do in their position? I’m Sophia Di Martino and this is True Spies from SPYSCAPE Studios. Mr. Wristwatch.

SEAN O'DRISCOLL: There was a Real IRA supporter who had visited a very senior Real IRA person in a prison in Northern Ireland. And he's like, “What can I do for the cause?” And the Real IRA member said, “Find David Rupert.” 

NARRATOR: August 15, 1998. Omagh, County Tyrone, Northern Ireland. Hundreds of people throng the town’s center for its midsummer carnival. Families, tourists, and locals alike are savoring the easy atmosphere of a country now at peace. The 33-year-long Troubles are finally a thing of the past, brought to an end just a few months ago by the Good Friday Agreement. In the midst of the celebrations, two men drive a red Vauxhall Cavalier down the town’s bustling market street and park up. Exiting the vehicle, both men turn a corner, enter another car, and drive off. A few minutes later, Ulster Television receives a phone call: "There's a bomb, courthouse, Omagh, main street, 500 pounds. Explosion, 30 minutes." The dormant machinery of the Troubles cranks back into gear. The TV station passes the warning on to the police. The police quickly usher the celebrating crowds away from the courthouse. But there’s a problem. The bomb isn’t at the courthouse.

SEAN O'DRISCOLL: The town was actually packed around the car bomb because the police were moving civilians up that way away from where they thought the bomb was. 

NARRATOR: Another phone tip is received. The bomb is in fact on Main Street.

SEAN O'DRISCOLL: But the notice that they had called in was way too short.

NARRATOR: At 3:10 pm, before the crowds can be redirected, the 500-pound bomb packed into the abandoned car goes off.

SEAN O'DRISCOLL: It killed 31 civilians. Absolutely horrific. Injured hundreds upon hundreds of people. The worst bombing ever happened in Northern Ireland. 

NARRATOR: Now, the promise of the Good Friday Agreement and peace in Northern Ireland hangs in the balance only months after being signed. Shortly after the bombing, a newly formed group claims responsibility - the Real IRA.

SEAN O'DRISCOLL: And they were doing just about everything they could to try and bring the agreement down.

NARRATOR: The British and American governments are desperate to make the peace hold though.

SEAN O'DRISCOLL: They would really do everything they could to try and put the Real IRA out of business. 

NARRATOR: And help comes in an unlikely form. Whoever said spies need to be inconspicuous?

SEAN O'DRISCOLL: He is a very big man, six-foot-six, and just a huge, broad man.

NARRATOR: And only a few years before, this man had never even heard of The Troubles.

SEAN O'DRISCOLL: He really knew almost nothing about Ireland. 

NARRATOR: In this episode of True Spies, you’ll hear the story of one of the most outlandish - and from certain perspectives - one of the most significant spies in modern history. A man who felt more at home behind the wheel of an 18-wheeler truck than in the shadowy world of espionage. A man who would end up traveling thousands of miles from home, and infiltrating a notorious terrorist cell at a time of fraught political unrest.

SEAN O'DRISCOLL: Everybody was saying, “Who's the big Yank? Who's this guy? What's he all about?”

NARRATOR: All while knowing the risk of being caught was a death sentence.

SEAN O'DRISCOLL: If they had known what David was doing, he would have been tortured first and then killed because he knew absolutely everyone and everything and what they were doing.

NARRATOR: It is indeed an unusual spy story. But then David Rupert always stood out from the crowd.

SEAN O'DRISCOLL: When he was a very small boy, he was in teenage clothes. He just towered over every other kid.

NARRATOR: This is Sean O’Driscoll, a lawyer, journalist, and author of The Accidental Spy, a book about David Rupert. For Sean, the key to understanding this unusual hero is his physical stature - 6’ 6” and over 300 pounds.

SEAN O'DRISCOLL: It basically kind of defined him his entire life because he is a very big man. 

NARRATOR: Leaving school at 16, David fell naturally into physical work. First at a construction company. Then, he tried his hand at professional wrestling. But it was trucking that proved to be his lifelong love.

SEAN O'DRISCOLL: That was mostly how he made his income - going across America from New York to Los Angeles, sometimes bringing car parts and steel to Detroit. 

NARRATOR: David’s second great love in life was women.

SEAN O'DRISCOLL: He was definitely a player. He really was fascinated by women and always in pursuit of them. And given his height, it seems to have worked to his advantage.

NARRATOR: But the relationships themselves invariably did not work out, with David marrying and divorcing three times before his 40th birthday. And his business ventures were no more stable.

SEAN O'DRISCOLL: He had a clothes shop and all kinds of things. He was running a diner, a small hotel, sometimes he was making a lot of money and really thriving. But then other times he was really struggling.

NARRATOR: Even his one true passion couldn’t be depended on for a stable income. Though the trucking industry boomed in ‘80s America, David’s own trucking business did not.

SEAN O'DRISCOLL: One of his companies was declared bankrupt.

NARRATOR: And so, at a loose end, David wound up in Florida in the early ‘90s.

SEAN O'DRISCOLL: For a trucking job. And in the meantime, he was just basically hopping around bars, checking out the scene, checking out the women in Florida. 

NARRATOR: One night, David is at his usual haunt, Jimmy B’s - a beach bar where patrons knock back shots to a booming 1990s rock soundtrack. But this evening, David hears something else over the din at Jimmy B’s. It’s a sound unlike anything he has come across before.

SEAN O'DRISCOLL: This folk music and traditional Irish music.

NARRATOR: The music is drifting over from a bar across the street. David’s curiosity gets the better of him.

SEAN O'DRISCOLL: He decided to go over there one day himself, in this Irish bar called the Harp and Thistle.

NARRATOR: There David meets a stunning red-head by the name of Linda Vaughan.

SEAN O'DRISCOLL: Who was very well up in the Democratic Party in Florida. 

NARRATOR: Struggling to hear her over the live band, David invites Linda out to the deck to talk. There she regales him with stories of her work in politics.

SEAN O'DRISCOLL: He kind of played along with it because he thought Linda was very hot and wanted to be with her.

NARRATOR: Linda’s political passions didn’t stop at America’s borders.

SEAN O'DRISCOLL: She was also connected to NORAID, which is the US fundraising ring of the IRA. 

NARRATOR: Knowing nothing of Irish politics, David feigns interest. As the evening draws to a close, he invites Linda back to his apartment.

SEAN O'DRISCOLL: And then they started dating. 

NARRATOR: It’s not long before David realizes just how involved in dissident Irish politics Linda is.

SEAN O'DRISCOLL: Linda had very good IRA connections in Donegal, in particular, in the northwest of Ireland. 

NARRATOR: And soon, she’s invited David to join her on a trip there. Intrigued, David agrees and the two set off for the Emerald Isle in mid-1992.

SEAN O'DRISCOLL: So when they arrived there, he met various Republican people and in particular a guy called Joe O’Neill.

NARRATOR: A staunch opponent of the emerging peace process, Joe O’Neill had walked out of the Provisional IRA - the predominant paramilitary group opposed to British rule in Northern Ireland. Upon leaving, O’Neill set up a splinter group, the Continuity IRA.

SEAN O'DRISCOLL: And they were the initial threat to the peace process.

NARRATOR: Alongside his politics, Joe O’Neill ran a nationalist pub in Donegal. Its name? Joe O’Neill’s. The first time David visits the place, he hears the rebel songs Four Green Fields and Come Out ye Black and Tan. This is a whole new world to the American trucker.

SEAN O'DRISCOLL: Joe O’Neill was what's now known as a dissident and he believed that the fight should continue. So he expressed all of this to David Rupert. 

NARRATOR: Both hard-drinking lovers of history, David and Joe click.

SEAN O'DRISCOLL: David's just a very good natural talker. He can talk about just about anything. And all his time in trucking, going across America, he would listen to audiobooks non-stop. So he’s quite a knowledgeable person. The two just bonded quite well. 

NARRATOR: After a few days, David and Linda return to the US. There, the relationship fizzles out. But David’s love for Ireland does not. Over the next year, he returned four times to see his friend, Joe O’Neill, and Ireland’s west coast, a world away from America. At the end of the last of these trips, Joe drives David back to his hotel. The two smile, shake hands, and go their separate ways. Back in the US David tries to pick up the pieces of his trucking business, having now relocated back to Chicago.

SEAN O'DRISCOLL: In an absolutely enormous center where different trucking companies operated from. 

NARRATOR: One day, in July 1994, David receives a visitor at that trucking center. And not just any visitor. He’s an FBI Agent.

SEAN O'DRISCOLL: Agent Buckley, a very aggressive agent came in.

NARRATOR: Agent Buckley slams an envelope on David’s desk. Inside are photographs. Photographs of David and Joe O’Neill, shaking hands outside an Irish hotel. Buckley points at David, saying...

SEAN O'DRISCOLL: You're mixing with IRA people. You're a terrorist and you're in a lot of trouble.

NARRATOR: But by now, David has been in the trucking business for 20 years. He has dealt with everyone from the mafia to fraudsters and the police. He knows not to roll over in a situation like this.

SEAN O'DRISCOLL: He felt that the FBI agent was bluffing with him. And he said, “Look, I've got nothing to tell you.”

NARRATOR: And what do you know? David’s instinct was right. Buckley had been bluffing. Soon, the disgruntled agent walked out. At the time of the encounter, the situation in Northern Ireland was changing significantly. The Provisional IRA had agreed a temporary ceasefire, signaling its openness to talks with the UK government.

SEAN O'DRISCOLL: There was intense interest in America because there was growing concern about dissident Republicans, those Republicans who were completely opposed to this peace and wanted to keep fighting and they were starting to emerge, Joe O'Neill being one of them.

NARRATOR: A few weeks later, FBI Agent Ed Buckley is back in David’s office.

SEAN O'DRISCOLL: But this time, the approach was very different. And he's like, “Look, you don't have to tell us anything, but let us pay for a trip to Ireland for you.”

NARRATOR: David pauses. 

SEAN O'DRISCOLL: And he kind of thought, “Well, if the FBI would pay for it, why not? I'm not going to give them anything anyway.”

NARRATOR: David even invites his new girlfriend along. The manager of the trucking plaza, Maureen. Soon enough, the happy couple are vacationing in Ireland. All paid for by the FBI.

SEAN O'DRISCOLL: The FBI are playing the long game and they're willing to pay for a few trips just to create a bond between themselves and David and also to compromise David because once you accept government money like that, then you have crossed over to the other side, whether you think you have or not.

NARRATOR: At 6 pm on February 9, 1996, US President Bill Clinton’s national security advisor received a phone call at the White House. On the other end was Gerry Adams - leader of the IRA’s political wing, Sinn Fein. The ceasefire was about to break. One hour later, a 3,000-pound truck bomb detonated in London’s financial district, killing two people. David Rupert and his now-wife Maureen watched the news footage in horror. By now, they had traveled to Ireland several times at the FBI’s expense, feeding back any scraps of information they overheard. But there was nothing significant. Disgusted at the renewed bombings, David met with Buckley again and this time, it’s David who makes a proposition.

SEAN O'DRISCOLL: He suggested that he lease a bar in Donegal. 

NARRATOR: To most FBI agents, this would have sounded like lunacy. But Agent Buckley was desperate. Some Irish Americans were just as appalled at the idea of the IRA laying down their weapons as many of the paramilitaries themselves, which was bad news for an FBI agent like Buckley.

SEAN O'DRISCOLL: Because the dissidents were starting to really fundraise through an organization called Friends of Irish Freedom, and they were very active in Chicago and were directly funding terrorism in Ireland, whereas in other cities they were just helping political prisoners. 

NARRATOR: Needing all the help he can get, Buckley asks David to tell him more about the bar. 

SEAN O'DRISCOLL: It was called the Drowes. Actually, it's only a few feet inside the [county] Leitrim, which is the next county over, and it came with its own caravan park, which was ideal because a lot of IRA people would holiday there. And it was the ideal IRA meeting place. 

NARRATOR: What’s more, David was ‘in’ with Joe O’Neill, the man heading up resistance to peace talks. He was as close to the dissident movement as anyone the FBI had. Buckley agrees to finance the lease on the pub, some $8,500. In return, David would step up his spy work, giving the FBI as much information as he could find out: how they were financed, who the big players were, what attacks they had lined up.

SEAN O'DRISCOLL: So the FBI unbeknown to anybody was actually in the Irish pub business through David. 

NARRATOR: Joe O’Neill is delighted that his good friend has come all the way from America to join the bright lights of the Donegal hospitality industry. Sensing an opportunity, David asks Joe if there is anything he could get for him from the US. “Detonating cords, plastic explosives, and detonators,” Joe replies.

SEAN O'DRISCOLL: And Joe went into this in-depth and how David was to do this. 

NARRATOR: “Hide the bomb parts in children’s toys,” Joe says. “Then ship them to this school in Donegal.”

SEAN O'DRISCOLL: They had a teacher in a school in Donegal who was a sympathizer to the Continuity IRA, so Joe had done this before.

NARRATOR: David says he’ll do what he can. When he reports the school, with its IRA-friendly teacher, back to Agent Buckley he’s applauded for his efforts.

SEAN O'DRISCOLL: The significance of David for Americans was really increasing.

NARRATOR: So much so that, in 1997, David signed a contract with the FBI to the tune of $2,500 a month to be their eyes and ears within Joe O’Neill’s Continuity IRA. His codename? Mr. Wristwatch. But by now, it wasn’t just the Americans who were interested in David Rupert. Later that year, MI5 also came knocking.

SEAN O'DRISCOLL: They were very excited when the FBI told them about David. They offered him more money and then they brought him over to England for training.

NARRATOR: In England, David immediately clicks with his MI5 handler.

SEAN O'DRISCOLL: David couldn't believe the difference between the FBI and MI5. He found MI5 far, far more professional than the FBI was. They just had this ability to blend in, in a crowd. Whereas, the FBI was very noticeable.

NARRATOR: As one of the first pit stops on his tradecraft crash course, David’s handler takes him on a tour of Winchester.

SEAN O'DRISCOLL: And showed him a statue of Alfred the Great and explained that this is the first British spy who was able to infiltrate a Viking camp.

NARRATOR: As the two of them gaze in admiration at the first British spy, David learns what sort of espionage MI5 want him to conduct. With another ceasefire in place, peace talks were now progressing in Northern Ireland. There was hope that The Troubles could finally be brought to an end but not everyone was ready to put the conflict to bed.

SEAN O'DRISCOLL: There was growing concern about dissident Republicans, those Republicans who were completely opposed to this peace and wanted to keep fighting.

NARRATOR: But by late ‘97, MI5 were discounting Joe O’Neill’s Continuity IRA. It seemed the organization’s bark was worse than its bite.

SEAN O'DRISCOLL: They're far more interested in the purity of their Republicanism and being right and actually doing anything. So their members were getting frustrated and wanted to move on to other organizations.

NARRATOR: And MI5 were concerned about one in particular.

SEAN O'DRISCOLL: It didn't have a name at the time, but it had centered around the Quartermaster General of the Provisional IRA. In other words, the man who held all the weapons and explosives’ bunkers, was a man called Mickey McKevitt.

NARRATOR: Mickey McKevitt had walked out on the Provisional IRA after it agreed to peace talks with the UK government and he took many members with him. By early 1998, the fledgling organization had set up a roadblock on the Irish border, telling motorists they were the IRA - the Real IRA. The name stuck.

SEAN O'DRISCOLL: They had all the contacts. They had the weapons. They had the bombs. They knew how to construct the bombs and they were willing to do it.

NARRATOR: So now, MI5 wants David to shift his attention from Joe O’Neill’s Continuity IRA and instead work on penetrating Mickey McKevitt’s Real IRA. And when the breakthrough Good Friday Agreement was signed a few months later, the FBI pressed David to up the ante.

SEAN O'DRISCOLL: The Clinton administration was very, very proud of this agreement that took years upon years of American negotiation.

ARCHIVE, BILL CLINTON: It is easier to stay with the old grudges and the old habits, but the right thing to do is to reach for a new future of peace. 

SEAN O'DRISCOLL: And the FBI explained to David that that the FBI wanted results before the Clinton administration was to end because they knew that whoever took over wouldn't have the same interests in Ireland and therefore they wouldn't get the same funding. So they really wanted to close things down. 

NARRATOR: ‘Closing things down’ meant tying up the loose ends of dissident activity after the Good Friday Agreement. In other words, getting hard evidence on some of the most dangerous men in Ireland at a time when they were most agitated.

SEAN O'DRISCOLL: They started setting off car bombs in town centers in Northern Ireland, giving a warning in advance, but trying to destroy town centers in Northern Ireland. 

NARRATOR: David was charged with exposing these very men and he knew exactly what would happen if the Real IRA caught on to his identity. The fate of informants often ended up on the news, including one David had met.

SEAN O'DRISCOLL: They set up a roadblock for him and then he disappeared. And no one knew where he was for two years until they dredged the canal in Newry and found he was still in his car at the bottom of the canal. And so, that was the kind of pressure that David was under. 

NARRATOR: Then, in August 1998, the stakes climbed even higher, as the Real IRA carried out the worst bombing attack in Northern Irish history killing 31 people and injuring over 300 others in the small town of Omagh.

SEAN O'DRISCOLL: There was absolute revulsion in Britain and Ireland to this and a determination then - from the British and from the Americans - that they would really do everything they could to try and put the Real IRA out of business. That's where David really became their key ‘asset’ - in the lingo of spying. 

NARRATOR: And David had an ace up his sleeve. By now he was the courier for all funds to Ireland from the American group, Friends of Irish Freedom. Every time he went to Ireland, David brought $10,000 with him from these supporters to hand over to the cause.

SEAN O'DRISCOLL: Which made him very popular with Republicans. 

NARRATOR: And now he planned to use that leverage to penetrate the Real IRA. David says to some of his former Continuity IRA contacts that he too wants to go over to the Real IRA. Eventually, he gets a meeting with Mickey McKevitt. As with Joe O’Neill before him, McKevitt clicks instantly with David.

SEAN O'DRISCOLL: And of course David, every time he saw him, was able to put 10 grand on the table. So that made him welcome.

NARRATOR: Soon, David meets McKevitt’s wife, who is practically Republican royalty.

SEAN O'DRISCOLL: Bernadette Sands McKevitt, the sister of Bobby Sands, who died on a hunger strike in 1981.

NARRATOR: Bernadette also likes this huge American. Gradually, he’s ushered into their inner circle. He’s even offered a seat on the Real IRA’s Army Council.

SEAN O'DRISCOLL: McDevitt wanted an American member on the Army Council so that there could be absolute verification that the money that they were receiving from America was going in the right way, and also that they would inspire confidence in their American supporters that they had a place on the table.

NARRATOR: The FBI and MI5 can hardly believe it.

SEAN O'DRISCOLL: This was a huge, huge development - for the British in particular - because now they would have an asset within the Real IRA Army Council who could report back on everything that they were doing.

NARRATOR: And McKevitt has a particular job for David.

SEAN O'DRISCOLL: McKevitt wanted ultra-high-tech bombs to show the provisional IRA that we're taking it to another level.

NARRATOR: The thing was, the best equipment wasn’t available in Ireland. But arms-loving America? That was another story...

SEAN O'DRISCOLL: They didn't want to order it and bring it over because it might be caught along the way.

NARRATOR: So, McKevitt tasks David with bringing the gear over himself.

SEAN O'DRISCOLL: McKevitt said he wants to ‘overshadow Omagh’, as he calls it, by pulling off, in IRA terms, a ‘spectacular’ in Britain on the scale of what the Provisional IRA pulled off in Brighton at the Conservative Party conference.

ARCHIVE AUDIO: “An IRA bomb exploded at the Grand Hotel in Brighton. Margaret Thatcher, working on her papers at two in the morning, narrowly escaped death.” 

SEAN O'DRISCOLL: Something like that would grab international headlines and convince American supporters that they were succeeding in undermining the British government and also undermining Northern Ireland. 

NARRATOR: David makes several equipment runs to America but each time he comes back only with the electronics requested, feigning excuses about the weaponry itself not being ready. Eventually, some of McKevitt’s men start to become suspicious. “This brash American continually over promises and under-delivers,” they thought. “Something is going on.” And they intended to find out what it was. At one Real IRA Army Council meeting, an engineer confronts David over a software disk.

SEAN O'DRISCOLL: And he said, “How do we know what's on this?” 

NARRATOR: David’s heart sinks.

SEAN O'DRISCOLL: He thought he had been uncovered.

NARRATOR: But somehow, instinct kicks in.

SEAN O'DRISCOLL: It's kind of a well-established spying thing. If you're confronted on that level, you confront back and you shout about how offended you are. 

NARRATOR: “I came all the way from America with this,” David yells. “It’s exactly what you asked for. If you don’t want it, I’ll tell you precisely where you can put it.”

SEAN O'DRISCOLL: So then somebody had to intervene between them and calm the situation down. 

NARRATOR: And McKevitt has David’s back. After all, he’s going to great lengths to provide them cash and equipment.

SEAN O'DRISCOLL: They really trusted him and over time, really opened up to him.

NARRATOR: McKevitt tells David everything from how the Real IRA’s London cells operated to their plans to bomb a British Navy ship docked on the Irish border. He also shares his ambitions to assassinate then Prime Minister Tony Blair. And David, in turn, relays everything to the FBI and MI5.

SEAN O'DRISCOLL: He was writing nightly emails, sometimes several emails a day using encrypted software. And it kept them up-to-date with absolutely everything. 

NARRATOR: Several plots are foiled thanks to David’s intel but not all of them. One that slips through the net is the bombing of Hammersmith Bridge in 2000. Another, an RPG attack on MI6 headquarters in London. But soon, MI5 spots an opportunity in David’s reports.

SEAN O'DRISCOLL: McKevitt said that Colonel Gaddafi in Libya - who had given the IRA all of their explosives and had given them millions of dollars - he was no longer interested in supporting Irish Republicanism because Tony Blair had basically reached out to him. So they needed a new foreign channel and they were thinking about who that might be. And then, McKevitt suggested Saddam Hussein in Iraq. And the British then saw that was their opportunity to really nail the Army Council of the Real IRA by pretending to get the Iraqis involved.

NARRATOR: If they themselves posed as Saddam’s henchmen, MI5’s agents were likely to get a sit down with the Real IRA; potentially gathering hard evidence against the group. Encouraged by David, the Real IRA make overtures to the Iraqi government. Then, posing as an Iraqi journalist, an MI5 agent faxes a Real IRA address.

SEAN O'DRISCOLL: The wording of it was very carefully chosen to make it look like they were in with the Iraqi government and had things to discuss.

NARRATOR: A meeting is arranged.

SEAN O'DRISCOLL: The so-called journalist told them that he's actually from the Iraqi government and they wanted to help out.

NARRATOR: McKevitt is encouraged by reports of the meeting. Soon, he starts speaking with the Iraqi ‘journalist’ himself over the phone.

SEAN O'DRISCOLL: They really went along with it.

NARRATOR: Further meetings are arranged. Eventually, several Real IRA Army Council members sit down with Iraqi government personnel across Europe - or at least who they thought were Iraqis - and at one of these meetings.

SEAN O'DRISCOLL: They even wrote out a list on the table of what they wanted, including wire-guided missiles and plastic explosives, just a huge amount of equipment they were looking for. And this was written on a napkin.

NARRATOR: The Real IRA men only show the Iraqis the list, deliberately not handing it over.

SEAN O'DRISCOLL: Then the British agent posing as an Iraqi pretended to wipe his nose and picked it up as they were talking and distracted them and then put it in his pocket as evidence. 

NARRATOR: Now possessing hard evidence, the British waste no time.

SEAN O'DRISCOLL: Those three members were arrested in a spa town in Slovakia while meeting the supposed Iraqis again. They were extradited to London and were given 30 years in prison each.

NARRATOR: This constituted a major coup. But to get McKevitt, more evidence was needed, which created tension between the FBI and MI5.

SEAN O'DRISCOLL: Because the FBI is very much a police organization, they want to go to court. Whereas, on the British side, there were a spying organization and they are prepared to keep people in organizations like the IRA for decades - and have done that.

NARRATOR: And to MI5, bringing down McKevitt would inevitably expose David Rupert, their mole at the heart of the Real IRA. The man who was feeding them gold dust about the organization continually. But slowly, MI5 began to come around to the FBI’s way of thinking. Perhaps it would be worth exposing a star operative for a catch this huge.

SEAN O'DRISCOLL: The British began to see their point of view - that it could be done with David's help, that David could become the chief witness against Mickey McKevitt in the case. Nothing like this had ever been achieved before. 

NARRATOR: But the thing was: David was under the impression he would never have to testify.

SEAN O'DRISCOLL: He fought them for a long time, and there were all sorts of negotiations.

NARRATOR: The FBI invite David and his wife Maureen to a luxury resort in Wisconsin.

SEAN O'DRISCOLL: Some barristers from the Irish Prosecution Service went over there as well. So it really became this big conference about what to do, to convince David that he would be okay.

NARRATOR: Yes, he would have to go into Witness Protection eventually, the FBI tell him.

SEAN O'DRISCOLL: But while he was in Ireland, he would have absolutely rock-solid protection 

NARRATOR: The offer was this: During the trial in Dublin, David would stay at a US military base within a British RAF base in Suffolk.

SEAN O'DRISCOLL: So he would have double protection.

NARRATOR: Then, when he was called to testify, the British would fly him to Dublin in a private jet.

SEAN O'DRISCOLL: And then fly him back at the weekend so that he would be safe and Maureen wouldn't have to come over.

NARRATOR: But David still isn’t convinced. If the FBI and MI5 really wanted to see McKevitt behind bars - well, then they would pay for it. 

SEAN O'DRISCOLL: David knew that he could hold out for more money because they would really badly need him for this prosecution. 

NARRATOR: Eventually, a deal is reached. David agrees to testify.

SEAN O'DRISCOLL: Nothing like this had ever been achieved before - had been attempted - where you basically had three police forces in America, Ireland, and Britain all coming together for a prosecution. And so they decided that they would do simultaneous arrests in three jurisdictions - America, Britain, and Ireland - and round up as many people as they could with their main target being Mickey McKevitt, the Real IRA leader. 

NARRATOR: In the early morning of March 29, 2001, McKevitt heard a loud knock on his door. Opening it, he and his wife Bernadette were met by two Irish Special Branch officers. Behind them were 30 heavily armed Gardai, Irish police. Eventually charged with directing terrorism, McKevitt’s case came to the Irish Special Criminal Court in 2003. Flown in on the British Royal Jet, 6’ 6” American trucker David Rupert was the star witness. And his appearance broke new ground for another reason too.

SEAN O'DRISCOLL: Longest cross-examination in Irish legal history. 

NARRATOR: McKevitt’s defense lay into Rupert, trying to discredit him.

SEAN O'DRISCOLL: All the shenanigans of David's life were laid bare. When you've been married four times and you've done your share of womanizing, and you've had various companies that went bankrupt... That went on for weeks.

NARRATOR: The defense fails to land any serious blows to David’s testimony though. Soon, the case against McKevitt becomes undeniable. After nearly a month on the stand, he’s sentenced to 20 years.

SEAN O'DRISCOLL: Which is a life sentence in Ireland under a new offense, which was directing terrorism, brought in after the Omagh bombing. So that was the first conviction for directing terrorism, which was of huge significance. 

NARRATOR: Not long after, McKevitt gives up his lifelong cause.

SEAN O'DRISCOLL: From prison, he released a statement saying that the cause is now hopeless and that we should put down weapons. 

NARRATOR: A few Real IRA members try to continue the fight.

SEAN O'DRISCOLL: But they're pretty much out of operation at this point because they just don't have any support.

NARRATOR: To many in the FBI and MI5, David Rupert is one of the most successful spies in modern history.

SEAN O'DRISCOLL: He brought the Troubles to an end, in a way, by really dismantling the Real IRA because they were the last kind of holdout. And by being on the Army Council, by putting Mickey McKevitt away, by identifying the Saddam Hussein threat, he really, in all those levels, really flattened them. And also the fact that he was able to testify in court, which hadn't happened before, made it particularly significant in three different jurisdictions.

NARRATOR: Today, David and Maureen live quietly in America. That much, I can say.

SEAN O'DRISCOLL: He's gone on living his life but it's been very difficult for him to work because he fears exposure. And he has a rule that he'll never go to Chicago, or Boston, or New York - or anywhere where there's a significant Irish-American population.

NARRATOR: And for good reason.

SEAN O'DRISCOLL: I found out from a very, very reliable police source that there was an Irish-American Real IRA supporter who had visited a very senior Real IRA person in a prison in Northern Ireland. And he's like, “What can I do for that cause?” And the Real IRA member said, ”Find David Rupert.”

NARRATOR: David’s exact location today? That’s still classified. I’m Sophia Di Martino. Next time on True Spies, you’ll meet two glamorous sleeper agents in swinging New York.

Guest Bio

Sean O'Driscoll is a Dublin-based journalist, attorney, and author of The Accidental Spy. His investigative journalism has appeared in The New York Times, the Guardian and the Irish Times.

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