Julian Dorey Podcast #296

"Boston Kingpin UNLOADS on Whitey Bulger, Rats & FBI Corruption | Red Shea"

Guest: Red Shea
Host: Julian Dorey
Release Date: April 25, 2025

Episode Overview

In this gripping episode, Julian Dorey welcomes Red Shea—one of the last non-cooperating top men from Whitey Bulger’s notorious Irish mob. Shea recounts an unflinching portrait of street loyalty, his rise through Boston’s underworld, the corrosive culture of ratting, and enduring FBI corruption. This is a no-holds-barred, deeply personal look at survival under Bulger’s leadership, refusing to turn state’s evidence—even after realizing his idol was the ultimate “King Rat.”
Throughout, Shea’s passionate devotion to the old-school code stands in stark contrast to the snitch-heavy legacies of his boss and rivals.

Key Topics & Insights

Early Life & Boston Upbringing

Timestamp: 00:00–23:50

• Childhood Hardships: Without his father (who died of alcoholism) and raised by a strict mother and older sisters, Red gravitated towards older neighborhood men and street culture.
• First Fights: At age 5, after being brutally bullied by older kids, his sister dragged him out and demanded he learn to box.
  • Quote (Red):

    “I was enraged, at five years old... That’s when my sister grabbed me by the hand and said, 'You’re going to the gym and you’re going to learn how to box.'” (00:27)

• Boxing as Foundation:
  • Success in amateur and pro boxing, including iconic Southie traditions (Irish Baby Golden Gloves).
  • Early criminal hustle involved stealing cigarettes from delivery trucks and selling them back to local markets.

Boxing & The Crossroads with Crime

Timestamp: 23:51–47:55

• Boxing Mentors: Trainer Tommy Connors became a crucial father-figure—though, in a twist, later facilitated Red’s entry into drug dealing.
• Turning Pro: Moved to California to pursue boxing (went 9–0 professionally), but the allure of easy money from drugs eventually drew him back.
• Parallel to Others: Discussion of balance between sports and easy cash from crime—the “cocaine cowboy” era.
  • Quote (Red):

    “You know, it’s a tough life, if you don’t have the money… That said, I started in California… but the money, you know.” (41:22)

Entry into Organized Crime

Timestamp: 47:56–68:00

• From Gym to Crew: Connections from the boxing gym linked him to Whitey Bulger’s men—Southie’s Irish mob, not the “Winter Hill Gang” (which had long since fractured).
• Rise Through the Ranks: By age 19, Red was importing kilos from Miami, eventually becoming a main supplier for Bulger’s organization.
• Street Code (Omerta): Instilled from an early age—never rat, handle your punishments solo.
  • Quote (Red):

    “You take your lumps and bumps. That’s it…And as you get into bigger stuff…it’s the same premise—you never rat. The stakes just get higher.” (69:02)

• Tests of Loyalty: Bulger, suspecting everyone, led Shea into basement “tests”—facing down possible execution, refusing to give up friends.
  • Quote (Red, reliving the moment):

    “He cocked back the Uzi. He said, ‘I want more information.’ I said, ‘Do what you gotta do.’ I was ready to die for my friends and not give them up… After that, he said, ‘You passed the test. You’re in charge now.’” (19:56)

“Playing Chess, Not Checkers” — Whitey’s Manipulations

Timestamp: 68:01–107:31

• Whitey as Father Figure & Mastermind: Charismatic, calculating, always several moves ahead.
  • Quote:

    “He was a very, very intelligent man… everybody else was playing checkers, he was playing chess.” (23:01)

• Myth vs. Reality: Bulger maintained a strict public myth of not touching drugs, but orchestrated and profited from wide-scale trafficking via proxies.
• FBI & Rats: Chronic FBI corruption—hundreds of informants, including Bulger and top associates, shielded by agency handlers (notably Connolly and Morris).
  • Shea:

    “The number two in charge says... those Irish guys the DEA wants, aren’t they our informants? …‘You get on the phone immediately and warn Boston.’” (16:00)

• Sacrificial Lamb: Bulger used Shea’s proven loyalty to shield himself from indictments—ensuring he took the fall but wouldn’t cooperate.

The Code vs The Culture of “Rats”

Timestamp: 107:32–167:38

• Absolute Loyalty: Shea, repeatedly given opportunities to cooperate, refused even after learning Bulger was a federal informant.
  • Quote:

    “I walked in a man, I’m walking out a man… just because Whitey’s a rat, we don’t rat.” (10:54, 166:49)

• Disdain for Cooperators: Strong emotions about podcast guests glorifying “rats”; demands harder questions from interviewers.
  • On modern-day mob “personalities”:

    “Stand up guys have the right to talk about being a stand up person. Not a rat...even if you were going away, you’re still a fucking rat. That’s how it is.” (11:48)

• The Internal Mirror:
  • Quote:

    “When they look in that mirror, they see the person they really are—a rat. And that’s the bottom line… they try anything they can to make themselves feel better.” (13:40)

Detailing the Arrest and Prison Experience

Timestamp: 143:43–167:38

• The Arrests:
  • Shea knew the DEA was closing in, but Bulger assured him to “keep going, just be careful.” Red: “My antennas were going off, but it was too late by then.” (143:15)
• Betrayal Realized: Only later—already in prison—did Shea discover the truth about Bulger’s informant status.
  • Quote:

    “When I called home… it felt like somebody reached through the phone and ripped my heart out… the loyalty I gave that man… my legs buckled a little bit, believe it or not.” (165:21)

• Opportunity to Cooperate: With five years left in a 12-year sentence, he refused to testify against anyone, despite repeated offers.
• Solidarity in Solitude:
  • Never ratted in prison, even when “stuck in a cell with a guy I didn’t know—told him, you better get out of here, it ain’t gonna be pretty.” (174:16)
  • Rejects the snitch “Matt Cox” podcast scene, upholds the old code.
• Plea Deal: Ultimately took 12 years (as opposed to 20-to-life), not for talking, but because his lawyer played the “look at what you’re doing to this kid” card. (161:33)

Whitey Bulger’s Fall & Aftermath

Timestamp: 164:48–191:36

• On Whitey’s Exposure & Life on the Run:
  • “Even after they were outed, there were plenty on the street that stayed solid—never ratted, never would.” (167:17)
• FBI Corruption and the “Rat Pipeline”:
  • Surveillance bugs always found and foiled, courtesy of within-the-house tips from Bulger’s FBI handlers.
• Reactions to Whitey’s Arrest & Death:
  • “When he was killed in jail, I was disappointed. I was definitely, definitely disappointed that he died—that I didn’t do it.” (193:01)
• The Unforgiving Mirror:
  • “When I look in that mirror… I can walk down any street in America… but when those rats walk down the street, they’re wondering: ‘is that guy looking at me like I’m a rat?’” (195:33)

Pop Culture, Media Work, and Life After Prison

Timestamp: 2:02–End

• Hollywood Consulting:
  • Advisor on “The Departed” and “Black Mass”—worked closely with Mark Wahlberg, Johnny Depp. “Mark changed my life… helped me get my book deal.”
  • Vivid story of visceral reaction seeing Johnny Depp in full Whitey makeup:
    • “I wanted to attack Johnny Depp. Because he looked so much like Whitey Bulger.” (186:14)
• Respect from Mark Wahlberg:
  • “Mark changed my life… he knew I was never a rat and that’s what intrigued him.” (03:05)
• Book Writing:
  • “RAT BASTARDS” became a New York Times bestseller. Whitey himself reportedly had a copy in hiding.
• Boxing Legacy:
  • Continues to train youth, speaks fondly of lifelong rivalry and friendship with Mickey Ward.

Notable Memorable Moments & Quotes

1. The Test of Loyalty:

   “He cocked back the Uzi… I was ready to die for my friends and not give them up in a basement.” (19:56)

2. On Modern-Day Mob Podcast Guests:

   “Stand up guys have the right to talk about how to be a stand up person. Not a rat.” (12:57)

3. On the Omerta Code:

   “Same premise you learnt in the neighborhood as a kid… the stakes just get higher.” (69:02)

4. On Mother’s Forgiveness & Family Pain:

   “I honored my mom… I gave the eulogy and said: my mom said, ‘You were all a gift to me.’” (63:42)

5. On Whitey’s Death:

   “I was disappointed… that I didn’t do it.” (193:01)

Suggested Timestamps for Navigation

• [00:27] Learning to fight at age five after childhood attack
• [11:48] The “Rat” debate and disdain for cooperators
• [19:56] Basement loyalty test—facing Uzis, passing into top rank
• [69:02] Explaining the street code: “never rat”
• [99:50] The science of drug operation (“cocaine chemistry”)
• [130:20] On murders: why Red wasn’t indicted for hit jobs
• [134:54] The “rat tail” story—father-figure Whitey
• [165:21] Shock at discovering Bulger’s betrayal in prison
• [186:14] Reaction to Johnny Depp in Whitey makeup for “Black Mass”
• [193:01] Reaction to Bulger’s violent prison death

Tone & Language

Shea’s storytelling is candid, fierce, and unpolished—Boston street through and through. His loyalty code is absolute, and his contempt for “rat” culture is expressed in stark, sometimes profane language. Julian Dorey provides context, respectful challenge, and ensures explanations for non-expert listeners. Both trade dark humor and sharp Boston banter throughout, especially on stories of violence, prison, and criminal craft.

Final Thoughts

Red Shea provides a first-hand, unvarnished look into the rise and fall of Boston’s Irish mob under Bulger, filtered through the lens of someone who never compromised the old code—even as everyone above him did. For those fascinated by true crime, codes of honor—and the cost of loyalty—this episode is essential listening, featuring rare authenticity and chilling insights into one of America’s most notorious criminal empires.

Notable Mention:

• “RAT BASTARDS: The South Boston Irish Mobster Who Refused to Rat” (book by Red Shea)
• Red Shea’s own podcast launching soon! (Watch for announcements from Julian Dorey.)