The Rise and Fall of Diddy – Episode 6: "What They Found and What They Couldn’t"

Podcast: The Rise and Fall of Diddy
Host: Jesse Weber (Law&Crime)
Date: October 21, 2025

Episode Overview

In this pivotal episode, host Jesse Weber guides listeners through the critical evidence phase of Sean “Diddy” Combs’ federal trial. The focus: what investigators seized during dramatic federal raids on Combs’ properties, how prosecutors tied this evidence to the broader allegations of abuse, control, and sex trafficking, and why the “smoking gun” was more elusive than headlines suggested. The episode delves into the challenges of linking evidence—drugs, weapons, financial transactions, digital content—directly to Combs amidst a chaotic, celebrity-fueled environment, featuring expert commentary from former federal agents and forensic specialists.

Key Discussion Points & Insights

1. Setting the Scene: The Raids and Evidence (01:03 - 04:44)

• Dramatic Raids
  In spring 2024, federal agents raided Diddy's Los Angeles and Miami homes, making headlines with their discoveries: illegal weapons, assorted drugs, and other bizarre items.

• The Evidence Inventory
  Homeland Security agent Gerard Gannon led the detailed walk-through for the jury:

  • Drugs in a Gucci bag: cocaine, ketamine, MDMA, Xanax, methamphetamine.
  • A "Puffy"-engraved box in the bathroom: MDMA capsules, hallucinogenic mushrooms.
  • Weapons: a loaded .45 handgun in a guard shack; two dismantled AR-15s with no serial numbers in the master closet.
  • Sexual paraphernalia: 18 pairs of platform heels, a sex toy, 25 bottles of baby oil, 31 bottles of lubricant.
  • Hidden cell phones in Balenciaga boots.

• Expert Commentary (Colin Schmidt, former FBI)
  “You have weapons with shaved off serial numbers, and then you have weaponry that is, frankly, weapons of war.” (03:39)
  The prosecution framed this setting as a calculated environment for coercion, not just celebrity excess.

2. Connecting Evidence to Alleged Crimes (04:44 - 07:46)

• Who Had the Power?
  Gannon testified that security was provided by friends and staff, not professionals—raising questions about access and control.

• Prosecution’s Theory
  The government pushed the narrative that drugs and weapons weren’t just props—they were tools of control. But as Schmidt noted, prosecution still had to prove “care and control” of these items on Combs himself—not just their existence in his homes.

  “Those are all party drugs… indicative of what their hypothesis was. It was just a gigantic orgy of craziness, and these drugs were there to fuel that behavior.” (06:11 – Colin Schmidt)

3. The Challenge: Whose Stuff Was It? (07:46 - 08:44)

• Defense’s Leverage
  Defense attorneys seized on the chaos of the Combs properties—hundreds of guests, staff, hangers-on—a revolving door where almost anyone could have possessed these items.
• A Weak Link
  Schmidt commented, “He had literally hundreds of people streaming through these properties at all times.” (06:59)
  The prosecution’s “most difficult hurdle” was proving the evidence was Diddy’s, not simply found in Diddy's orbit.

4. “Physical Evidence Alone Wasn't Enough”: Digital & Financial Forensics (08:44 - 19:30)

• Digital Evidence, Patterns, and Timelines (08:44 - 15:54)

  • Agent Joseph Serciello’s Role
    Serciello presented a forensic deep-dive: texts, calls, payments, travel records—44 key entries from 2021-2024.
    Notable findings:

    • After the Cassie Ventura lawsuit (2022), “freakoff” events shifted from hotels to private residences.
    • Hotels billed for “bodily fluid damage” and “carpets and linen soaked in baby oil,” echoing what was seized at Combs’ home.
    • Financial records showed thousands in cash withdrawals aligning with alleged assault dates.

  • Explosive Text Exchange
    Cassie (2017): “you beat my head in, treat me like a hooker.”
    Diddy replied: “any other woman would have been happy.”
    (10:44 – 10:54)

  • Pattern Over Pieces
    Serciello’s charts illustrated a network:

    • Payments matching encounters.
    • Travel records, guests, messaging, and illicit videos all plotted chronologically.

  • Heather Barnhart (Forensic Specialist)
    Explained the labor-intensive process of extracting, analyzing, and correlating digital evidence:

    “One device could easily take three days from beginning to, all right, I’m sitting and I’m looking at something and trying to make sense of data.” (11:54)

5. The Art of Digital Storytelling (15:54 - 19:50)

• Video Evidence Complexity
  Barnhart detailed that while cell phone metadata can provide location, timestamps, device details, and even camera angles, connecting them to specific individuals or criminal intent is a massive undertaking.

  "If you have forensic software that can help you pinpoint a specific face...that's really helpful. But without that, ...it's a lot of work, and it's a lot of manual review by the investigator and examiner." (15:54)

• Financial Forensics
  Payments weren’t just spreadsheets: Serciello cross-referenced wire transfers, app payments, hotel bills, and flight bookings—mapping money to the events’ timeline.

  • Barnhart:

    "When it's a major Enterprise. You are going to see keywords that are being used. You will see really detailed communications because there's so many moving parts." (17:44)

  • Defense’s Argument
    The defense didn’t deny the mountain of evidence but questioned: Did any of it—drugs, weapons, messages, money—tie directly to Diddy, or just to the chaos surrounding him?

6. Key Takeaways and The Trial’s Turning Point (19:12 - 20:13)

• Complexity as a Double-Edged Sword
  The case became a contest of patterns versus proof—mid the dazzling volume of evidence and damning details, the jury needed clear, undeniable links back to Sean Combs.

  "I think the Diddy case is a good lesson. That simple is better. That's the bottom line." (20:07 – Colin Schmidt)

Notable Quotes & Memorable Moments

• On Weapons:
  “You have weapons with shaved off serial numbers, and then you have weaponry that is, frankly, weapons of war.”
  — Colin Schmidt (03:39)

• On Drugs and Hypotheses:
  "Those are all party drugs...it was just a gigantic orgy of craziness, and these drugs were there to fuel that behavior.”
  — Colin Schmidt (06:11)

• On Forensic Challenges:
  “One device could easily take three days from beginning to, all right, I’m sitting and I’m looking at something and trying to make sense of data.”
  — Heather Barnhart (11:54)

• Diddy’s Text to Cassie:
  “Any other woman would have been happy.”
  — Sean Combs (10:54)

• On Making the Case:
  "The Diddy case is a good lesson. That simple is better. That's the bottom line."
  — Colin Schmidt (20:07)

Important Timestamps

• 01:03 – Jesse Weber introduces the details of the raids and what was found in Combs’ homes
• 03:39 – Colin Schmidt explains the legal significance of the weapons seized
• 06:11 – Schmidt discusses how drugs functioned as alleged tools of coercion
• 10:44 – Notable Cassie-Diddy text exchange revealed
• 11:54 – Heather Barnhart explains digital forensic timelines
• 15:54 – Challenges of matching video evidence to events/people
• 17:44 – Financial forensics as evidence of enterprise
• 20:07 – Colin Schmidt summarizes prosecution’s dilemma

Conclusion

This episode masterfully unpacks the difference between sensational discovery and courtroom proof, exploring how federal agents and prosecutors presented their arsenal of evidence, the technology and painstaking work required to connect the dots, and the legal hurdle of attribution in a world as sprawling as Diddy’s. Through expert voices and meticulous breakdowns, listeners see why the prosecution’s task was formidable—and why, despite the spectacle, the true measure was what could be proven, not just found.

Next episode preview: The testimony of hotel security, alleged cover-ups, and how Combs’s team tried to keep evidence hidden—a deeper dive into the machinery protecting Diddy’s empire.