Podcast Summary

Podcast: New Books Network – On the Cusp: Strategy and Ethics
Episode: Seamus McElearney with Barbara Finkelstein, "Flipping Capo: How the FBI Dismantled the Real Sopranos"
Date: February 26, 2026
Host: Alfred Marcus
Guest: Seamus McElearney, former FBI agent and co-author (with Barbara Finkelstein) of Flipping Capo: How the FBI Dismantled the Real Sopranos (Chicago Review Press, 2025)

Overview

In this episode, Alfred Marcus interviews Seamus McElearney, a former FBI agent and author, about his book chronicling the inside story of how the FBI “flipped” mobster Anthony Capo to take down the DeCavalcante family—the real-life inspiration for The Sopranos. The discussion ranges from investigative strategies and ethical dilemmas to the organizational parallels between the mob and the FBI, the evolution of law enforcement priorities, and lessons on leadership, ethics, and whistleblowing.

Key Discussion Points & Insights

Seamus’s Background and Perspective

• Early Influences:

  • Grew up in the Bronx, worked at his father’s gas station. Learned work ethic & people skills.
  • Later worked in banking and audit, skills crucial for investigative work (adapting quickly, analyzing structures).
  • Noted surprising similarities in structure between the FBI and the mob.

  “The FBI is all about structure... and lo and behold, that's what the mob is about. The mob is all about structure and not enforcing laws. They're actually trying to break laws, but they have their own rules.” (Seamus, 01:43)

• Path to the FBI:

  • Entry inspired by chance meeting with an agent; drawn by the job’s variety.
  • Persistence was key:

  “My motto throughout life has always been persistence beats resistance. So I was determined to become an agent.” (03:04)

The DeCavalcante Family: The “Real Sopranos”

• Organizational Prowess:
  • The mob operated as a “shadow business enterprise,” controlling unions (Laborers 394, Asbestos 1030), starting their own school, rigging bids, and running “no show/no work” jobs.
  • Their influence reached the ability to shut down all Jersey job sites to enforce their will.

  “That shows you how powerful they were.” (Seamus, 06:46)

• Parallel to Legitimate Business:
  • Used union tampering as a cash cow; tactics furthered their control across multiple sectors.
  • Unwilling business partnerships (developers, contractors) were common.

  “A lot of developers ended up working with them, I would suspect.” (Host, 08:00)
  “Unwillingly. Yes.” (Seamus, 08:06)

Investigative Tactics: The Long, Meticulous Work

• Years-Long Cases:

  • Organized crime investigations often took 3–4 years; heavy reliance on consensual recordings and proactive witnesses.
  • Example of witness Ralph Guarino—made 300 tapes over two years, providing a treasure trove of coded but damning evidence.
  • The Sopranos TV show: Mobsters recorded joking about their portrayals, used as powerful trial evidence.

  “All we had to do was press play… What's worse is having your own voice on tape talking about the Sopranos, admitting that that is you in the show. So that was horrible for them.” (Seamus, 10:21)

• Back Office Work:

  • Transcribing, integrating evidence, and managing surveillance is meticulous, sometimes undervalued labor.

• Interagency Coordination:

  • Specialized squads for each major crime family.
  • Historic achievement: The C10 squad dismantled both the DeCavalcante and Bonanno families at the same time (1999–2004).

Ethics and the Use of Informants

• Controlled Criminal Activity:

  • Tightly managed: e.g., allowing informants to sell goods or untaxed cigarettes, but only when the FBI had pre-seized them or the “stolen” goods were fake.
  • Never allowed “drugs to walk” into the community.

  “You want to make sure that you don't fully rely on AI... you really want to make sure that you give it a full listen yourself, too.” (Seamus on AI and tape review, 15:50)
  “There is a level of trust, but we're constantly watching them... It’s hard to dispute when you have the photo, the recording, the witness on the stand.” (18:04–19:10)

• Risks:

  • Some informants do go rogue; when discovered, their relationships are terminated—sometimes with an arrest.

Impact of 9/11 and Resource Reallocation

• Aftermath:
  • Organized crime investigations halted for about four months; all resources shifted to counterterrorism.
  • Over time, staffing for organized crime units was sharply reduced. By 2026, New York has just one such squad.

  “If the mob has been around for 125 years, if you don't keep a close eye on them, they are going to rebuild.” (Seamus, 26:16; 27:49)

• Witness Security:
  • Entering the program requires jail time in "witness security" facilities before relocation and identity changes.

  “It's not like you just get a whole new pass on life. You have to do time in jail for your heinous acts that you've done.” (Seamus, 21:02)

The Relationship with Anthony Capo

• Building Trust:
  • Leveraged shared interests in sports (Steelers/Yankees vs. Cowboys) to build rapport and gain cooperation.

  “A happy witness is a good witness, right? And the more I can make him feel comfortable and relaxed, the more he's going to tell me.” (Seamus, 28:41)

• Confessions and Implications:
  • Capo provided extensive testimony, implicated himself and others in multiple murders (notably Fred Weiss’s).
  • Capo became a "made man" through his violence and eventually a successful protected witness.

Organizational Lessons on Strategy and Ethics

• Parallels to Corporate Cases:
  • “Flipping” in organized crime mirrors tactics in white-collar cases—trade leniency for information.
  • Getting 12 jurors to agree is always tough; cases go forward only with very strong evidence.
• Resource Allocation:
  • New York has specialized, shifting branches. The Bureau continuously reallocates resources to address perceived threats (organized crime, white-collar, terrorism, violent crime).
• Leadership & Squad Turnarounds:
  • Seamus led significant organizational shifts—e.g., stabilizing the Columbo Family unit, increasing productivity, and maximizing consensual recordings.

  “I always believe in leading by example. In my world, everyone has a voice.” (Seamus, 59:43)

Whistleblowing & Ethical Courage

• Difficult but Essential:

  • Whistleblowing and flipping require personal courage; being true to oneself and knowing when to step forward is central to ethical conduct.

  “If it doesn't feel right, you know, do you really want to work there?... So it takes guts to come forward, but it's the right thing to do.” (Seamus, 55:38)

• Advice for Future Generations:

  • Oversight is critical; remain true to your ethical core.
  • Whistleblowing should be a last resort if internal remedies fail, recognizing personal sacrifices involved.

The Changing Face of Crime

• Rise of Cyber and Remote Scams:
  • Fraudsters have become more sophisticated—phishing, business email compromise, cyber-theft.
  • Old-school bank robberies are rare; now, criminals “rob you blind online.”

Notable Quotes & Timestamps

• “Persistence beats resistance. So I was determined to become an agent.” (Seamus, 03:04)
• “The Decalvacante family controlled unions... started a school... controlled the business from the ground up.” (Seamus, 05:17)
• “What's worse is having your own voice on tape talking about the Sopranos, admitting that that is you in the show.” (Seamus, 10:21)
• “A happy witness is a good witness, right? And the more I can make him feel comfortable and relaxed, the more he's going to tell me.” (Seamus, 28:41)
• “If you don't continue to apply the pressure, they're going to rebuild.” (Seamus, 27:49)
• “I always believe in leading by example. In my world, everyone has a voice.” (Seamus, 59:43)
• “If it doesn't feel right, you know, do you really want to work there?... So it takes guts to come forward, but it's the right thing to do.” (Seamus, 55:38)

Timeline of Key Segments

| Timestamp | Segment/Topic | |------------|----------------------------------------------------| | 00:05 | Introduction, Seamus’s background | | 01:43 | Mob & FBI: Organizational structure parallels | | 05:17 | Mob business strategies & union infiltration | | 08:49 | Investigative methods, the role of recordings | | 13:20 | How the DeCavalcante case began | | 16:49 | Informants & ethical lines in investigations | | 21:02 | Witness security program: phases & realities | | 26:07 | Post-9/11 Bureau shift and resource reduction | | 28:36 | Building trust with Capo, sports banter | | 31:05 | Capo's confessions and mob murder specifics | | 35:35 | Organized crime vs. white-collar cases | | 38:25 | Capo’s outcome: from mobster to success story | | 42:53 | White-collar cases: parallels & case origination | | 45:48 | FBI resource allocation strategies | | 59:43 | Leadership: transforming unstable squads | | 61:02 | High-volume recordings and modern jury expectations| | 63:37 | Retirement reflections and legacy | | 65:04 | Reflections on missing FBI work/people |

Memorable Moments

• Mobsters recorded referencing The Sopranos show: a rare moment where pop culture overlaps directly with FBI evidence, embarrassing the suspects in court. (10:21)
• Turning around a troubled FBI squad through inclusive leadership and transforming culture from “redheaded stepchilds” to high performers. (59:43)
• Detailing the stepwise, grueling path from informant to protected witness, dispelling Hollywood myths with a real look at the WITSEC process. (21:02)

Conclusion

This episode provides a rich, behind-the-scenes look at the practical and ethical challenges of long-term organized crime investigations, the evolution of FBI strategy, and the personal and moral considerations faced by agents and informants. For listeners interested in organizational strategy, law enforcement, or the ethical gray areas of justice, Flipping Capo and Seamus McElearney’s experiences offer both gripping stories and enduring lessons.