Casefile Presents: Suing Diddy

Summary

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Casefile Presents: Suing Diddy

Podcast: Casefile True Crime
Episode Date: September 18, 2025

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Overview

This episode introduces a gripping new story covered by Jack Lawrence, host of the podcast "One Minute Remaining." The tale centers on Derek Lee Cardello Smith, an incarcerated Michigan man who claims—and, according to some sources, has been awarded—a $100 million judgment against Sean "Diddy" Combs for sexual assault. Smith's allegations spiral far beyond the initial claim, detailing corruption, murder plots, and a life destroyed by a chain of chilling events. Through candid interviews and references to supporting documentation, the episode promises a crime story stranger than fiction, leaving both listeners and the show's host questioning everything they thought they knew about justice.

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Key Discussion Points & Insights

1. Introduction to the Case

• Background: The episode opens with the host introducing Jack Lawrence and his experience documenting the lives and cases of incarcerated individuals in the US, highlighting the uniqueness of Smith’s story.

  • “Three years ago, Jack Lawrence started a podcast called One Minute Remaining, documenting conversations with incarcerated people across the United States.” – (00:07, B)

• The Lawsuit:

  • A Michigan inmate, Derek Lee Cardello Smith, claims to have been awarded a $100 million judgment against Sean "Diddy" Combs for sexual assault.
  • “This is in the matter of Derek Lee Cardello Smith versus Sean Combs. Sean Puff Daddy Combs, also known as Sean Pete Diddy.” – (00:33, A)
  • "He has now been awarded a 100 million dollar judgment against Sean Diddy Combs for sexual assault." – (00:44, C)

2. Smith’s Shocking Allegations

• Tales of Corruption and Murder:

  • Smith’s story includes wild allegations involving attempted murder-for-hire, namely a plot to kill a police officer’s wife.
  • "They tried to hire me to kill a Detroit police officer's wife. Her name was Rose Cobb." – (01:09, C)

• Wrongful Imprisonment:

  • He claims he is now wrongfully incarcerated as a result of these events.
  • "This is literally the woman who destroyed my life after her life was destroyed." – (01:20, C)

3. The Mystifying Legitimacy of Smith’s Claims

• Evidence and Documentation:

  • Host Jack Lawrence struggles to discern truth from fiction but is repeatedly surprised to find real-world evidence backing up unexpected claims.
  • “Whenever he started to doubt what he was hearing, Derek would point to legal documents, paperwork, even news articles that seemed to back him up.” – (01:25, B)
  • “One minute he's telling me this thing that cannot be true, and then I Google it and there it is in black and white. He telling the truth.” – (01:43, D)

• Disbelief and Intrigue:

  • The story shakes the host's confidence in his ability to tell reality from fantasy.
  • “I feel like I'm part of some sort of Twilight Zone right now, I'll be honest.” – (02:06, D)

4. Broader Impact and Hook for Listeners

• The saga has made international headlines and is billed as a story that upends expectations about prison narratives and celebrity justice.
• “This is not just another prison story. It made headlines around the world and left Jack questioning everything.” – (01:56, B)
• “You're on the cusp. You're on the cusp of something extremely huge.” – (02:17, C)
• The episode promises listeners a unique and mind-bending true crime experience.
• “If you think you've heard it all before when it comes to crime stories, trust me, you haven't heard anything like this.” – (02:10, B)

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Notable Quotes & Memorable Moments

• On the Story’s Wild Nature:
  • “The claims being made by Derek Lee Cardello Smith were nothing short of mind blowing tales of corruption, murder.” – (01:01, B)
• On the Blurred Line Between Truth and Myth:
  • “Dude, I don't know what to believe anymore. Like, honestly, one minute he's telling me this thing that cannot be true, and then I Google it and there it is in black and white. He telling the truth.” – (01:43, D)
• On the Feeling of Unreality:
  • “I feel like I'm part of some sort of Twilight Zone right now, I'll be honest.” – (02:06, D)
• On the Case’s Impact:
  • “You're on the cusp. You're on the cusp of something extremely huge.” – (02:17, C)

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Timestamps for Important Segments

• 00:07 – Jack Lawrence’s background and podcast journey
• 00:33 – Case introduction: Smith vs. Sean Combs
• 00:44 – Claim: Smith's $100 million judgment for sexual assault
• 01:09 – Murder-for-hire allegations regarding Rose Cobb
• 01:20 – Smith describes his alleged wrongful imprisonment
• 01:43 – Host grapples with legitimacy of Smith’s claims
• 02:06 – Host articulates his “Twilight Zone” feeling
• 02:17 – Derek Smith teases the case’s bigger significance

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Conclusion

Casefile Presents: Suing Diddy launches with a compelling mix of jaw-dropping allegations, credible supporting documents, and a host left reeling between disbelief and amazement. Promising an unpredictable journey through the intersection of crime, celebrity, and the justice system, this episode hooks listeners with the assurance that, in true crime, fact is often far stranger than fiction.

Transcript

[A]

This call is from a correctional facility and is subject to monitoring and recording.

[B]

Three years ago, Jack Lawrence started a podcast called One Minute Remaining, documenting conversations with incarcerated people across the United States. From drugs to arson, assaults and murders, even wrongful convictions. He thought he'd heard it all. That was until he met a man suing Sean P. Diddy Combs for 100 million doll million dollars.

[A]

This is in the matter of Derek Lee Cardello Smith versus Sean Combs. Sean Puff Daddy Combs, also known as Sean Pete Diddy.

[C]

There's a guy named Derek Lee Cardello Smith, a Michigan man who's incarcerated. He has now been awarded a 100 million dollar judgment against Sean Diddy Combs for sexual assault.

[B]

The claims being made by Derek Lee Cardello Smith were nothing short of mind blowing tales of corruption, murder.

[C]

They tried to hire me to kill a Detroit police officer's wife. Her name was Rose Cobb.

[B]

A sexual assault, and ultimately what he says was his own wrongful imprisonment.

[C]

This is literally the woman who destroyed my life after her life was destroyed.

[B]

It was a story like nothing Jack Lawrence had ever documented before. And whenever he started to doubt what he was hearing, Derek would point to legal documents, paperwork, even news articles that seemed to back him up.

[C]

Do you even believe this guy and what he's saying?

[D]

Dude, I don't know what to believe anymore. Like, honestly, one minute he's telling me this thing that cannot be true, and then I Google it and there it is in black and white. He telling the truth.

[A]

Holy shit. What is going on?

[B]

This is not just another prison story. It made headlines around the world and left Jack questioning everything.

[A]

Hi, Jack.

[D]

I feel like I'm part of some sort of Twilight Zone right now, I'll be honest.

[B]

So if you think you've heard it all before when it comes to crime stories, trust me, you haven't heard anything like this.

[C]

You're on the cusp. You're on the cusp of something extremely huge.

[B]

Suing Diddy. The brand new podcast from Casefile Presents is out now. Wherever you get your podcasts.