The Spy Who Jailed the Omagh Bomb Plotter | Blowing up the Peace | Episode 2

Podcast: The Spy Who
Host: Raza Jaffrey (for Wondery)
Release Date: January 13, 2026

Episode Overview

This gripping episode explores the aftermath of the historic 1998 Good Friday Agreement through the harrowing events of the Omagh bombing and the perilous world of post-ceasefire Republican militancy in Northern Ireland. Spy David Rupert, working undercover for the FBI and MI5, moves ever closer to the heart of the Real IRA as they mount a deadly campaign against peace, including bombings in London and the plot to assassinate British Prime Minister Tony Blair. The episode unfolds through vivid storytelling, testimonies, and reconstructions, highlighting the blurred moral lines, personal danger, and the toll on communities.

Key Discussion Points & Insights

1. Opening: Violence in a "Peace" Era

[00:05–03:49]

• Vivid scene-setting with Mickey Donnelly, a former Provisional IRA man, now hardened by torture and lauded as one of the "hooded men".
• Donnelly, outspoken against the peace process, is violently attacked in his home by armed men—Republicans punishing dissension:
  • "Maybe this will teach you to keep that fucking mouth of yours shut." (Masked assailant, 02:15)
  • Donnelly's resolve against peace hardens despite the violence.

2. Omagh Bombing: Atrocity Strikes

[04:38–09:30]

• Two months later, Omagh, Northern Ireland: The bustling town is targeted with a 500-pound Real IRA/Continuity IRA car bomb.
• A chain of failed and confusing bomb warnings leads police to inadvertently herd civilians closer to the device.
• The bomb detonates, causing catastrophic loss:
  • "21 people are so far confirmed dead and more than 200 have serious injuries." (News report, 08:25)
  • Emotional impact on David Rupert and his wife Maureen witnessing news:
    • "Oh my God." (Maureen, 08:10)

3. Rupert's Dilemma: Loyalty, Danger, and Going Deeper

[09:31–17:30]

• Rupert, traumatized, calls his MI5 handler and is advised to lay low and return to the US—if given cover by Joe O’Neill (Continuity IRA contact).
• Joe O’Neill, deeply shaken, tells Rupert to flee:
  • "You should get yourself and Maureen back to the States. I don't want to see you two getting caught up in this mess." (O’Neill, 14:12)
• Mickey Donnelly, limping and embittered, contemplates switching allegiances from Continuity IRA to the more dangerous Real IRA.

4. The Real IRA: From Armed Struggle to Global Terror

[17:31–37:50]

• Summer 1999, Rupert and Donnelly meet Real IRA leader Michael McKevitt.
  • McKevitt’s ruthless ambition is clear; he mocks Donnelly’s old-school ideas of small-scale violence:
    • "We're planning a bombing campaign in London and you're talking about killing one police policeman." (McKevitt, 25:50)
• Rupert’s American fundraising credentials grant him pivotal access:
  • "Firstly, I'd like to move that we appoint Dave Rupert to the Army Council as a representative of our important fundraising partners in the US." (McKevitt, 30:48)
• Serious intent revealed:
  • Real IRA’s “sleeper agent” in Boston is tasked with assassinating Tony Blair.
    • "Who's he gonna assassinate?"
    • "Tony Blair, that's who." (McKevitt, 33:48)

5. Double Jeopardy: Fear, Suspicion, and Moral Strain

[37:51–49:00]

• Rupert endures increasing risk on operations—delivering encryption software, braving suspicion from Real IRA bomb-makers.
  • Sweating under scrutiny: "How do we know this hasn't been doctored?" (Bomb maker, 41:20)
• Meeting with Smith, the Real IRA’s US-based assassin, under intense FBI surveillance:
  • "Things are happening as big as you, big man. We're on a roll." (Smith, 47:05)
• Rupert’s conundrum: His actions directly enable lethal operations—he fears both discovery and the moral cost.

6. Operation London: Hammersmith Bridge Bombing

[49:01–58:55]

• MI5 tails Real IRA operatives in London, but are outmaneuvered:
  • "Bloody bomb just went off on Hammersmith Bridge. But it wasn't our target. Something's gone wrong." (MI5 officer, 54:40)
• McKevitt boasts to Rupert about the bomb’s success and outlines their new tactics:
  • Use of previously unknown local cells and Irish truckers to evade surveillance.
  • Acceleration of bombing campaign and reassurance that the assassination plan—code-named for Tony Blair—is imminent.

7. Crisis of Cover: Press Exposure Threatens Rupert’s Deep Cover

[58:56–End]

• Sunday Times article exposes Rupert as a "trucking millionaire" bankrolling the IRA.
  • McKevitt fumes: "Mickey bloody Donnelly is how. That journalist is one of his pets." (McKevitt, 01:03:00)
• McKevitt’s wife Bernadette voices the new severity of Rupert’s position:
  • "If he gets arrested and talks?... Forget the money. He's a liability." (Bernadette, 01:04:03)
• Rupert’s world threatens to crash—his role as a spy, trust with contacts, and even ongoing payments from MI5/FBI are all suddenly in doubt.
• Rupert signals MI5: "The Sunday Times has just blown my cover. I've got an ARM plus meeting tomorrow and things just might be."

Notable Quotes & Memorable Moments

"Maybe this will teach you to keep that fucking mouth of yours shut."
— Masked Attacker to Mickey Donnelly �[02:15]

"21 people are so far confirmed dead and more than 200 have serious injuries."
— TV News Broadcast heard by Rupert and Maureen [08:25]

"You should get yourself and Maureen back to the States. I don't want to see you two getting caught up in this mess."
— Joe O'Neill to David Rupert [14:12]

"We're planning a bombing campaign in London and you're talking about killing one police policeman."
— Michael McKevitt to Donnelly [25:50]

"Firstly, I'd like to move that we appoint Dave Rupert to the Army Council as a representative of our important fundraising partners in the US."
— Michael McKevitt [30:48]

"Who's he gonna assassinate? ... Tony Blair, that's who."
— McKevitt to Rupert and Army Council [33:48]

"How do we know this hasn't been doctored?"
— Real IRA Bomb Maker to Rupert [41:20]

"Things are happening as big as you, big man. We're on a roll."
— Smith (the assassin) to Rupert [47:05]

"Bloody bomb just went off on Hammersmith Bridge. But it wasn't our target. Something's gone wrong."
— MI5 Surveillance Officer [54:40]

"Mickey bloody Donnelly is how. That journalist is one of his pets."
— McKevitt (upon Rupert's exposure in the press) [01:03:00]

Important Segment Timestamps

• Violence against Mickey Donnelly: 00:05–03:49
• Omagh bombing & aftermath: 04:38–09:30
• Rupert's exit from Ireland post-Omagh: 09:31–14:50
• Inside Real IRA: meeting McKevitt, fundraising: 17:31–30:50
• Plot to assassinate Tony Blair revealed: 33:30–33:48
• Hammersmith Bridge bombing, MI5 surveillance: 49:01–54:40
• Rupert's journalistic exposure: 58:56–End

Tone and Style

• The episode is delivered in an urgent, evocative style, alternating between calm narration and tense dialogue.
• Real people’s words are dramatized, highlighting the authenticity, danger, and weariness of everyone involved.
• Vivid emotional beats—shock, horror, paranoia—pull listeners into both high-level intrigue and intimate moments of fear and choice.

In Summary

This episode powerfully chronicles one of the bloodiest post-peace moments in Northern Ireland and explores the terrifying world of modern underground militancy. As David Rupert navigates shifting allegiances, imminent violence, and the ever-present threat of exposure, listeners are given a rare, deeply human window into the shadow world of intelligence, betrayal, and survival. The pace is relentless, the stakes are real, and the moral lines are never clear.