Podcast Summary: "Michael & The Diddy Escort: 'Diddy Watched the Whole Time' | Shawn Dearing"

Podcast Information:

• Title: The Michael Knowles Show
• Host/Author: The Daily Wire
• Episode: Michael & The Diddy Escort: “Diddy Watched the Whole Time” | Shawn Dearing
• Release Date: July 19, 2025
• Description: The Michael Knowles Show dissects the chaos of politics and culture, providing incisive analysis on the day's top stories from Monday through Friday.

1. Introduction: Sean Dearing’s Background

Sean Dearing introduces himself as someone who grew up in Hawaii and later moved to Los Angeles. Initially uncertain about his career path, Sean tried college for three and a half years before entering the workforce. His first jobs included serving in restaurants and later working in the valet and bar industries in Las Vegas.

Notable Quote:

• Sean Dearing [02:26]: "I live in LA prior to that. You know, I'm born and raised in Hawaii and I was figuring out where I'm headed with life."

2. Entry into Escorting

Sean recounts how he transitioned from the bar industry to modeling at the encouragement of his girlfriend, leading him to create a profile on Model Mayhem. This eventually caught the attention of Garen James, the owner of the escort agency "Cowboys for Angels." Initially skeptical, Sean was convinced to meet James, which marked his entry into the escorting world.

Notable Quotes:

• Sean Dearing [03:19]: "It's sort of the, I think it's like the old school MySpace style of the model industry."
• Sean Dearing [04:34]: "The proper term would be the escort server. Well, not the terminology slipping me, but it's a prostitution."

3. The Escorting Experience and Working with P. Diddy

Sean describes his role as an escort, detailing how he was hired to spend time with wealthy women, including Cassie, P. Diddy's girlfriend. He explains the structured and performative nature of these encounters, emphasizing the control exerted by P. Diddy and the orchestrated environment designed to fulfill his depraved sexual desires.

Notable Quotes:

• Michael Knowles [01:35]: "P. Diddy has gotten off the hook for the worst charges that he faced pertaining to his freak offs and weird sex parties over decades."
• Sean Dearing [23:57]: "I show up to the address. I go up to the door, knock, and she opens the door."

4. Moral Realization and Exit from the Industry

As Sean continued his work, he began to witness the manipulative and abusive tactics used by other members of the escort agency. This included attempts to impregnate women deceitfully and the psychological abuse inflicted by clients. Realizing the moral degradation of his actions and the exploitation involved, Sean decided to distance himself from the industry. His turning point was witnessing the abusive behavior of individuals like the Dean of Medicine, which highlighted the depth of corruption and immorality within the escorting business.

Notable Quotes:

• Sean Dearing [15:04]: "One thing I realized, I love people."
• Sean Dearing [54:08]: "I realized how, how detrimental it really was for."

5. Legal and Media Exposure

Sean's involvement in the escorting world became public knowledge during the legal battles of P. Diddy, where Sean’s name and picture were revealed in court. The situation escalated when rapper 50 Cent posted Sean’s image with insinuations of P. Diddy’s misconduct, thrusting Sean into the mainstream media spotlight. Despite his reluctance, Sean gave interviews to clear his name and share his side of the story.

Notable Quotes:

• Sean Dearing [28:32]: "Revealed in court. And then it started to go mainstream when 50 posted that picture."
• Michael Knowles [48:04]: "But you saw some of it up close."

6. Final Reflections and Closure

In the latter part of the conversation, Sean reflects on his journey, expressing remorse for his participation in the exploitative system and his desire to move forward spiritually. He emphasizes his commitment to serving God and his struggle to reconcile his past actions with his current Christian beliefs. Sean also shares his hopes for the individuals he was involved with, wishing for their redemption and justice.

Notable Quotes:

• Sean Dearing [74:36]: "I love people. I could never do something so degrading to another individual."
• Sean Dearing [95:54]: "The only two words for Diddy is find Jesus."
• Michael Knowles [89:29]: "You can cooperate with God's grace."

Key Insights and Conclusions

• Moral Degradation: Sean’s story underscores the moral and spiritual degradation inherent in the escorting industry, particularly when intertwined with powerful and abusive figures like P. Diddy.

• Control and Exploitation: The narrative highlights how control and power dynamics are exploited in such environments, leading to the manipulation and abuse of vulnerable individuals.

• Personal Redemption: Sean’s journey from participation to realization and his quest for redemption illustrate the potential for personal transformation and the importance of spiritual guidance in overcoming past mistakes.

• Media’s Role: The role of media in exposing and exacerbating personal scandals is evident, raising questions about privacy, public perception, and the consequences of public exposure.

Notable Quotes with Timestamps

• Sean Dearing [00:00]: "So I don't know who I'm seeing. And so I show up to the address, I go up to the door, knock, and she opens the door."
• Michael Knowles [09:17]: "So this is still in operation?"
• Sean Dearing [18:51]: "Cause the arms of whatever system Diddy has are much bigger than any we can perceive that we know of."
• Michael Knowles [27:53]: "Had you just sat down, we're meeting for the first time, and you told me this story. It's not that I would have immediately called you a liar, but I would have been very skeptical about your claims."
• Sean Dearing [43:47]: "So there's a moment where doing. You know, we're naked and on a couch and Diddy kind of gets up and walks and she just kind of pauses and. Huh."
• Michael Knowles [54:16]: "If you're going to engage in an exploitative act, or if you're going to be subjected to an exploitative act, better it be with me than with some bad guy."
• Sean Dearing [86:34]: "I will always love and serve God."

Final Thoughts

This episode provides a harrowing glimpse into the dark underbelly of the escorting industry, especially when intersected with fame and power. Sean Dearing's candid revelations about his involvement with P. Diddy and the moral conflicts he faced offer listeners a profound narrative on sin, redemption, and the struggle between personal desires and spiritual values.