Dateline: True Crime Weekly – Episode Summary Episode: Sean Combs: A Personal Assistant and The Punisher Take the Stand
Release Date: May 21, 2025
Host: Andrea Canning
Produced by: NBC News

Introduction

In this gripping episode of Dateline: True Crime Weekly, host Andrea Canning delves deep into the high-stakes racketeering trial of Sean Combs, widely known as Diddy. Released on May 21, 2025, the episode titled "Sean Combs: A Personal Assistant and The Punisher Take the Stand" provides an in-depth look at the allegations against Combs, featuring testimonies from key witnesses that shed light on the inner workings of his alleged criminal enterprise.

David James’s Testimony: The Personal Assistant’s Account

Timestamp [00:01 – 07:22]

David James, Sean Combs’ personal assistant from the mid to late 2000s, takes the stand under a proffer agreement, granting him immunity to discuss any illicit activities he may have been involved in.

Chloe Melas, NBC News correspondent, reports from outside the courthouse:

[01:02] Andrea Canning introduces David James as "Combs' personal assistant during the mid to late 2000s."

David presents a multifaceted image of Combs, intertwining both the glamor and the alleged dark side of his professional life.

Key Points from Testimony:

1. Illegal Activities and Coercion:

   • James details how Combs allegedly pressured him and others to protect his reputation, even through illegal means.
   • He mentions procuring ecstasy for Combs and acting as an intermediary between Combs and drug dealers.

2. Daily Operations:

   • James describes his duties, such as fetching facial products specifically for Combs and ensuring Combs felt comfortable in any city by providing his preferred Heinz ketchup ([02:25]).
   • He recounts an incident where Combs allegedly ordered him to locate Suge Knight with the implication of potential violence ([04:11]).

3. Interactions with Security:

   • Security often joked about the threat of being fired if tired, emphasizing the high-pressure environment ([03:13]).
   • James was subjected to lie detector tests after accusations of theft, which he claims he passed ([03:34]).

4. Cover-Up Attempts:

   • James testifies about an incident involving Combs’ personal chef, where Combs allegedly instructed him to file a false police report claiming that Jordana (the chef) was the aggressor ([06:05]).

Notable Quote:

[05:30] "No one fired a gun that night, but Combs had people willing to do illegal things for him." – Andrea Canning

James’ testimony paints a picture of a controlled environment where Combs exerted significant influence and maintained strict oversight over illicit activities.

Cassie Ventura’s Mother’s Testimony: Unveiling Abuse

Timestamp [07:22 – 09:34]

Cassie Ventura’s mother takes the stand briefly, with the defense choosing not to cross-examine her. Her testimony focuses on the alleged physical abuse Cassie endured at the hands of Sean Combs.

Key Points from Testimony:

1. Discovery of Abuse:

   • Cassie’s mother recounts visiting Cassie in Connecticut during the 2011 holidays, where she observed bruises and signs of physical abuse ([07:31]).

2. Evidence of Abuse:

   • She revealed that Cassie took photographs documenting her injuries, which are now publicly available, showing extensive bruising ([08:10]).

3. Emails and Financial Demands:

   • An email from Cassie in December 2011 threatened the release of explicit videos unless demands were met ([08:25]).
   • Cassie’s mother claims that Combs demanded $20,000, which was briefly withdrawn from their home equity line of credit and sent to Bad Boy Entertainment. Remarkably, the money was returned to her account within days ([08:59]).

Notable Quote:

[08:53] "When I got that email, I was physically sick." – Cassie Ventura’s Mother

This testimony highlights the personal turmoil and alleged coercion Cassie and her family experienced, adding a deeply emotional layer to the prosecution’s case.

The Punisher’s Testimony: Unveiling Sexual Exploitation

Timestamp [09:34 – 13:05]

An exotic dancer, known professionally as The Punisher (Charay Hayes), testifies about his encounters with Sean Combs and Cassie Ventura in 2012.

Key Points from Testimony:

1. Sexual Encounters:

   • Hayes describes being hired to create a provocative setting for a couple, only to find Cassie Ventura instead of Janet and her husband ([10:04]).
   • He recounts witnessing Combs in compromising positions, including masturbating in the corner and instructing participants to cover themselves in baby oil ([10:45]).

2. Use of Baby Oil:

   • The Punisher explains that baby oil was used to create a glittering effect, aligning with Combs’ fetish for shimmering appearances. Authorities discovered extensive quantities of baby oil in Combs’ properties during raids ([10:51]).

3. Commercial Transactions and Travel:

   • Hayes emphasizes that these encounters were commercial transactions, with Combs paying him and having him travel across state lines for these activities ([11:18]).
   • He clarifies that while Combs’ defense claims these were consensual transactions, the prosecution sees them as part of a larger pattern of exploitation ([12:03]).

4. Control Over Cassie:

   • Hayes states that Cassie always sought Combs’ approval before engaging in sexual activities, suggesting manipulation and control ([12:08]).

Notable Quote:

[12:44] "This was all consensual," – Defense’s stance as highlighted by Andrea Canning.

Hayes’ testimony is pivotal in illustrating the alleged misuse of power and the orchestrated nature of Combs’ interactions with Cassie, challenging the defense’s narrative of consensual relationships.

Upcoming Developments

As the trial progresses, significant events are anticipated:

• Testimony from Kid Cudi (Scott Mascudi):

  • Known for alleging that Combs "blew up his car" out of jealousy over a brief relationship with Cassie Ventura, Kid Cudi’s testimony is expected to be a major turning point in the trial ([13:05]).

• Further Witness Accounts:

  • The prosecution aims to establish a comprehensive view of Combs’ criminal enterprise, reinforcing the argument that he orchestrated illegal activities through coercion and manipulation.

Notable Quote:

[13:21] Andrea Canning hints: "We're in for another wild ride tomorrow."

Conclusion

This episode of Dateline: True Crime Weekly intricately weaves together testimonies that depict Sean Combs not just as a music mogul but as an alleged orchestrator of a criminal empire fraught with drugs, coercion, and exploitation. The personal accounts of David James, Cassie Ventura’s mother, and The Punisher collectively build a narrative that challenges Combs’ defenses, setting the stage for a dramatic continuation of this high-profile trial.

Notable Quotes with Timestamps

• Andrea Canning [05:30]: "No one fired a gun that night, but Combs had people willing to do illegal things for him."
• Cassie Ventura’s Mother [08:53]: "When I got that email, I was physically sick."
• Defense’s Stance [12:44]: "This was all consensual."

Further Information

For more detailed coverage and updates on the Sean Combs trial, visit NBC News: Diddy on Trial.

Produced By: Franny Kelly, Alison Orr, Liz Brown Kurloff
Music By: Jesse McGinty
Executive Producer: Paul Ryan
Senior Executive Producer: Liz Cole

Stay tuned for the next episode of Dateline: True Crime Weekly for continued coverage of this landmark case.