The Spy Who: Jailed the Omagh Bomb Plotter

Episode 1: Friend, Foe or Fortune Hunter?

Hosted by: Raza Jaffrey & Indira Varma
Date: January 6, 2026

Episode Overview

This debut episode of "The Spy Who" delves into the real-life story of David Rupert, an American who became entangled in the Irish Troubles—and ultimately became a spy for both the FBI and British MI5. The show dramatizes the late-stage chaos of the Northern Ireland conflict, as hardline republicans resist peace and new alliances and betrayals unfold in the shadows. The narrative spotlights trust, deception, and dangerous double lives—posing the central question: Was Rupert a friend, foe, or a fortune hunter?

Key Discussion Points & Insights

1. Setting the Stage: The Troubles & Paramilitary Threats

• The episode opens in 1993, with Irish police surveilling Republican hardliners. The ongoing violence of "the Troubles" has killed thousands, and dissident factions seem eager for renewed escalation (01:05–03:30).
• The introduction of a mysterious "giant American" in Sligo raises alarms about American support for Irish dissidents—a recurring specter in the conflict.

2. Profiling David Rupert: A Man at a Crossroads

• David Rupert is introduced in 1994, running a struggling trucking business near Chicago. He’s framed as a "6’7”, heavyset trucker" with a chaotic personal life and mounting debts (07:52).
• The FBI approaches him not for tax issues, but due to his connections with Joe O’Neill, an IRA affiliate (08:20–11:05).

Quote:
"Sure. That's me on vacation in Ireland, saying goodbye to a friend." — David Rupert, explaining his photo to the FBI (09:07)

3. First Steps into Espionage

• Rupert, lured by the FBI’s unexpected offer, is asked to report on his Irish dealings. At first hesitant, he confides in his girlfriend Maureen and weighs the risks and rewards (17:00–22:45).
• Maureen, invested but cautious, supports him—recognizing the potential for both danger and financial escape.

Quote:
"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." — Maureen to Rupert (21:30)

4. Gaining Trust, Raising Stakes

• The podcast details how Rupert and Maureen integrate into Chicago’s Irish-American community, attending fundraisers and becoming trusted couriers for money intended for republican groups (28:45–31:25).
• The stakes rise when Joe O’Neill discusses smuggling bomb parts disguised as toys to Ireland, showing the chilling creativity and persistence of insurgent networks (34:00–36:15).

Quote:
"Detonating cords are contained in skipping ropes, and the explosives will be hidden inside teddy bears." — Joe O’Neill to Rupert (36:12)

5. Double Agent: MI5 Enters the Picture

• MI5, intrigued by Rupert’s access, recruits him directly, offering substantial additional pay. This cements Rupert's place at the heart of anti-peace republican networks (39:45–43:10).
• Norman, the MI5 handler, tests Rupert’s loyalty and moral limits, inquiring if he'd ever contemplate assassination for money—a test Rupert passes, insisting he won't kill (41:02–41:50).

Quote:
"I won't kill anyone. But I do expect to get paid for the risks I take. My help comes with a price tag." — David Rupert to MI5's Norman (41:30)

6. Splinter Groups and Escalating Plots

• The Real IRA is formed by Michael McKevitt after the Provisional IRA adopts the peace process, marking a new and more fanatical threat (45:20–47:10).
• Cooperative attacks between the Real IRA and Continuity IRA spark renewed violence, undermining the nascent peace (49:30–51:00).

7. The Good Friday Agreement—and Immediate Opposition

• As world leaders celebrate the 1998 Good Friday Agreement (55:00–57:00), Rupert learns firsthand that the hardliners are plotting to sabotage peace with fresh violence.
• He dutifully reports the plot to MI5, but suspicion among the republican ranks grows—a spy is suspected when plans are foiled (59:10–63:00).

Quote:
"If we do it within 24 hours of the deal, it will show what they agreed means nothing." — Joe O’Neill, plotting violence in response to the peace agreement (58:45)

Notable Quotes & Memorable Moments

• On the Spy World:

  "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." — Host Raza Jaffrey (05:20)

• On Justifying Violence:

  "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." — David Rupert, to Maureen (19:20)

• On Being Recruited:

  "You love Ireland. ... What if we pay for your trips? All you've got to do is tell us what you see and what you hear." — Agent Buckley, FBI (16:20)

• Motivation for Spying:

  "I've never told anyone before. Sometimes I look at my life and I see three failed marriages and a load of debts. I want my next marriage to last a life. And I want to do something more with my life." — David Rupert to Maureen (22:08)

Key Timestamps

• 01:05–03:30 — Introduction to Sligo surveillance, context of the Troubles
• 08:20–11:05 — FBI’s first confrontation with David Rupert
• 17:00–22:45 — Rupert weighs spying; discussion with Maureen
• 28:45–31:25 — Fundraiser scene in Chicago; money-laundering for IRA
• 34:00–36:15 — Smuggling bomb parts disguised as toys
• 39:45–43:10 — MI5 recruits Rupert; negotiation over pay and tasks
• 45:20–47:10 — Michael McKevitt founds the Real IRA
• 55:00–57:00 — Signing of the Good Friday Agreement
• 58:45–63:00 — O’Neill plots fresh violence, Rupert tips off MI5, suspicion rises

Flow and Tone

Rich with dramatized dialogue and sharply atmospheric narration, the episode tightrope-walks between tension, irony, and humanity. The hosts and characters maintain a tone that’s both candidly world-weary and quietly hopeful—never glamourizing violence, but always spotlighting its moral ambiguities. The genuine voices and perspectives of American outsiders, Irish Republicans, and intelligence officers all collide, forming a layered, compelling narrative.

Summary Takeaways

Episode 1 of "The Spy Who Jailed the Omagh Bomb Plotter" traces how an American trucker, caught between his own broken life and competing allegiances in Ireland, becomes a crucial double agent. The episode explores not only the operational details of undercover intelligence work amid the Troubles, but also the psychological and moral complexities—personal risk, divided loyalties, and the high price of taking sides.

Ideal for listeners interested in real-world espionage, Irish history, or the personal costs of living in the shadows.