The Spy Who — Episode 3: "The Spy Who Jailed the Omagh Bomb Plotter | The Reaping"

Podcast by Wondery | Hosts: Indira Varma & Raza Jaffrey
Original Air Date: January 20, 2026

Main Theme

This episode delves into the tense final act of the undercover operation that led to the downfall of Michael McKevitt, leader of the Real IRA, and principal architect of the Omagh bombing. Through the eyes of FBI and MI5 spy David Rupert, listeners are taken deep into the world of espionage, betrayal, and the immense psychological toll undercover work exacts, culminating in a high-stakes trial that tested new anti-terror laws and changed the course of Irish history.

Key Discussion Points & Insights

1. The Critical Error: The Disc Mix-up

• [00:04–03:30]
  • July 2000: David Rupert, undercover in Worcester, MA, accidentally gives IRA assassin Smith a disc containing his own spy notes for MI5, believing it was a disc with rocket launcher software.
  • Panic and dread ensue as Rupert realizes the potential exposure to his spymasters and to himself.
  • Quote:
    • “He's just given a trained IRA killer the disc containing the notes about his last trip to Ireland. Notes intended for his MI5 spymasters.” (Narrator, 02:56)

2. Operation Recovery & The Threat Escalates

• [04:00–07:30]
  • Rupert maneuvers to retrieve the original disc from Smith, fabricating a backstory involving his wife to appear casual.
  • Fortuitously, Smith seems distracted by a new romance and hasn’t checked the disc.
  • Real IRA’s high-profile attacks escalate: rocket attack on MI6 headquarters in London ([07:41]), tying the group’s actions directly to efforts destabilizing the peace process.

3. Inside the Real IRA: Tensions and State Sponsorship

• [09:50–13:00]
  • Rupert passes cash to McKevitt under the table in Dundalk.
  • McKevitt discusses the diminishing fundraising power and his desire for a new “state sponsor”—possibly even Saddam Hussein.
  • Quote:
    • “All we need, Dave, is a state sponsor to help us take things to the next level. In the 1980s, Gaddafi and Libya sponsored us… That’s what we need. Maybe someone like Saddam Hussein.” (McKevitt, 11:55)

4. MI5 vs. FBI: Clashing Timetables

• [13:01–17:40]
  • Internal debate between MI5 and FBI on when to close in and arrest. MI5 wants to keep the operation running to build more evidence, especially around these alleged state connections; the FBI wants arrests before the Clinton administration ends and priorities shift.
  • Tense negotiation buys MI5 a little more time: “If it starts heading south, we will move to arrests in the US immediately. And then you’re on your own with McKevitt.” (FBI officer, 17:16)

5. Technical Espionage and Paranoia

• [17:41–22:15]
  • Rupert, now posing as a “computer whiz,” sets up a doctored computer for McKevitt, planting MI5 surveillance tools.
  • Loyalty and trust: McKevitt brushes aside rumors of Rupert being a spy, but paranoia simmers.
  • Quote:
    • “Ignore Donnelly. He’s just bitter because he’s on the way out. He can’t deal with it.” (McKevitt, 21:35)

6. Final Sting: Arms Delivery in Worcester

• [22:16–28:45]
  • Rupert, under FBI surveillance, orchestrates the final evidence hand-off with Smith—receiving two dozen Uzis meant for the IRA.
  • Clashes with FBI handlers add psychological intensity:
    • “Yeah? How much is it worth if I’ve got a bullet in my head?” (Rupert, 25:55)
  • Smith’s casual attitude contrasts sharply with the tension.

7. The Human Fallout: Family and Sacrifice

• [29:00–33:00]
  • Rupert’s exposure forces the family into hiding; Maureen tells her daughter Dory the truth about years spent undercover.
  • Emotional impact highlighted as Maureen says goodbye, uncertain when they’ll meet again.

8. Testimony Dilemma: To Testify or Not?

• [33:01–38:40]
  • Irish police push Rupert to testify at McKevitt’s trial, but he refuses, fearing for his life and his family’s safety.
  • Quote:
    • “I have finished. I got you everything you wanted. You lot won’t be happy until I am dead.” (Rupert, 36:08)

9. The Saddam Hussein Ruse & Greenlighting Arrests

• [39:00–41:00]
  • MI5 runs a fake Iraqi arms deal, with an operative acting as a Saddam envoy.
  • Recorded calls with McKevitt talking about weapons and payment give authorities final needed evidence.

10. The Arrest and MI5’s Gamble

• [41:01–43:15]
  • Dawn raid on Michael McKevitt’s home in Blackrock.
  • McKevitt, unfazed at first by the charges; as evidence (including Rupert’s connections and receipts) mounts, concern sets in.

11. Rupert’s Reluctant Turn as Star Witness

• [43:16–51:00]
  • With pressure, Rupert ultimately agrees to testify, set up by a huge financial offer:
    • “I’m authorized to offer you, you and Maureen, just over $19,000 a month for the rest of your life.” (FBI Handler Mark, 46:30)
    • Additional bonus, and cancellation of over $700,000 in taxes.
  • Maureen’s emotional support is pivotal in his decision.

12. The Historic Trial

• [51:01–56:00]
  • June 18, 2002: McKevitt is brought before a juryless court, faced with a packed gallery of victims’ families.
  • Rupert’s appearance as witness is a turning point.
  • McKevitt’s defense—focused on Rupert’s credibility—fails to shake the evidence.
  • Quote:
    • “Non payment of a loan is pretty far short of murder.” (Rupert, 54:10, responding to attacks on his debts)

13. Aftermath and Legacy

• [56:01–end]
  • McKevitt convicted, becomes first person sentenced under new Irish anti-terror laws.
  • Rupert and Maureen remain in hiding; his evidence later aids a civil suit linking McKevitt and others to the Omagh atrocity.
  • Real IRA’s decline post-conviction, new dissident groups arise but struggle to gain momentum.
  • Inquiry continues around whether more could have been done to prevent Omagh bombing.

Notable Quotes & Memorable Moments

• Rupert on the risk of undercover life:

  • “Yeah? How much is it worth if I’ve got a bullet in my head?... I’ve been doing this for six years buddy. I never ask questions I don’t need to. You are gonna get me killed.” (25:55–26:40)

• McKevitt on state sponsorship:

  • “All we need, Dave, is a state sponsor to help us take things to the next level… Maybe someone like Saddam Hussein.” (11:55)

• Maureen to her daughter:

  • “David isn’t with the IRA. He’s been spying on them for the FBI and MI5. We both have for the past six years.” (31:31)

• Irish police plea to Rupert:

  • “If we don’t nail McKevitt this time, then the Real IRA will keep killing people. There could be another Omagh bombing.” (37:10)

• Rupert calculating the price of treachery:

  • “That is a generous offer.” (47:32, after FBI’s financial proposal to testify)

Timestamps for Important Segments

• [00:04] — Prologue: Rupert’s fatal disc error
• [07:41] — Real IRA’s rocket attack on MI6
• [11:55] — McKevitt discusses state sponsorship
• [13:01] — MI5/FBI operation strategy meeting
• [21:35] — McKevitt dismisses spy rumors about Rupert
• [25:55–26:40] — Rupert vs. FBI handler over safety and evidence gathering
• [31:31] — Maureen reveals their spy work to her daughter
• [37:10] — Police stress the urgency of Rupert’s testimony
• [46:30] — FBI handler offers Rupert long-term financial security for testifying
• [51:01] — McKevitt’s trial and Rupert’s testimony
• [56:01] — Aftermath, decline of Real IRA, and legacy

Episode Flow and Tone

The episode combines dramatic reconstruction with nuanced psychological insight, balancing the personal cost of espionage against the cold calculation of international security operations. Tension is palpable throughout—whether in the nerve-wracking disc mishap, the high-stakes negotiations between agencies, or the emotional strain on Rupert’s family.

Dialogue is portrayed in a gritty, realistic style, closely echoing the real words and mood of the players involved. The hosts and script maintain a gripping, fast-paced narrative throughout.

Closing Reflections

Episode 3 exposes the inner workings and high human cost of intelligence work in the aftermath of one of the darkest moments in recent Irish and British history. The mounting pressure, split loyalties, and the pivotal role of a single embedded agent offer a window into the shadow world where political decisions and human lives intersect—all the way up to the historic conviction of a terrorist leader.

Next Episode Preview:
Journalist Charlie Higson and author Kara McGoogan discuss the vast, often surprising scale of espionage during the Troubles—teasing more revelations about the agents, their methods, and the long shadow of betrayal these stories cast.