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The Diddy Diaries

The Diddy Diaries: The Downfall of Sean Combs is a raw, unflinching look at the dramatic collapse of one of hip-hop’s biggest moguls. For decades, Sean "Diddy" Combs seemed untouchable—a figure who rose from the streets to become a titan of the music, fashion, and entertainment industries. His Bad Boy Entertainment label defined a generation of hip-hop, and his entrepreneurial spirit made him a household name. But beneath the surface of this glittering success lay darker currents—currents that have

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All Episodes

12:11

The Billionaire's Playboy Club: A Memoir By...

The Diddy Diaries ·

2025/10/26

Virginia Roberts Giuffre’s unpublished memoir The Billionaire’s Playboy Club recounts her recruitment into Jeffrey Epstein’s world as a 16-year-old working at Mar-a-Lago, where she says Ghislaine Maxwell lured her in with promises of opportunity and travel. The manuscript describes how she became trapped in Epstein’s orbit, allegedly forced into sexual encounters with powerful men, including Prince Andrew, and ferried across his properties in New York, Florida, and the Virgin Islands. Giuffre paints

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49:10

Mega Edition: Prince Andrew Gets Tagged As A "Sex...

The Diddy Diaries ·

2025/10/26

Prince Andrew first earned the nickname “Randy Andy” back in the late 1970s and 1980s when British tabloids latched onto his reputation as the monarchy’s playboy prince. His love life became constant tabloid fodder — actresses, models, and socialites were all part of his orbit, and the press leaned into it with sensational headlines. Andrew seemed to enjoy the attention at the time, often photographed at nightclubs or on yachts surrounded by women. The nickname stuck because it fit the image — the

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40:02

Mega Edition: Denise George And Her Side Of The...

The Diddy Diaries ·

2025/10/26

In her interview with The Times, Denise George portrayed herself as the lone crusader working for the people of the U.S. Virgin Islands who would not be intimidated by the legacy of Jeffrey Epstein. She described the private island known as “Hell Island” and the systemic abuse of young women that took place there, and explained how her office pursued justice for the victims even while facing massive political and financial pressure.In her Bloomberg interview, George reflected on her aggressive legal

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32:26

Mega Edition: Prince Andrew And The Royal Lodge Saga...

The Diddy Diaries ·

2025/10/26

Prince Andrew’s Royal Lodge controversy stems from the fallout of his disastrous ties to Jeffrey Epstein and the long shadow of that scandal. After his 2019 BBC Newsnight interview, which spectacularly backfired, Andrew was stripped of his public roles, military titles, and royal patronages. Once a senior working royal, he became an isolated figure whose financial situation—and entitlement to royal housing—were both thrown into question. Yet, despite his exile from public life, Andrew has continued

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39:47

Mega Edition: Prince Andrew Can't Sweat. Unless...

The Diddy Diaries ·

2025/10/26

In his now-infamous 2019 BBC Newsnight interview, Prince Andrew claimed he was unable to sweat at the time Virginia Giuffre alleged they danced together at a London nightclub in 2001. He attributed this to a “peculiar medical condition” caused by “an overdose of adrenaline in the Falklands War.” However, photographs later surfaced showing Andrew attending parties in Saint-Tropez during the early 2000s, visibly perspiring under the Mediterranean sun. These images directly undercut his bizarre defense

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11:41

Clayton Howard Blasts Diddy AND Cassie Ventura In An...

The Diddy Diaries ·

2025/10/26

Clayton Howard, a former male escort and frequent participant in Diddy’s private sex parties known as “freak-offs,” has filed a lawsuit accusing both Sean “Diddy” Combs and Cassie Ventura of sex trafficking, coercion, and abuse. According to his claims, he was recruited to perform sex acts under the guise of high-end parties, only to find himself drugged, manipulated, and transported across state lines for increasingly degrading and violent encounters. He alleges that Diddy exercised complete

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10:27

Clayton Howard Blasts Diddy AND Cassie Ventura In An...

The Diddy Diaries ·

2025/10/26

Clayton Howard, a former male escort and frequent participant in Diddy’s private sex parties known as “freak-offs,” has filed a lawsuit accusing both Sean “Diddy” Combs and Cassie Ventura of sex trafficking, coercion, and abuse. According to his claims, he was recruited to perform sex acts under the guise of high-end parties, only to find himself drugged, manipulated, and transported across state lines for increasingly degrading and violent encounters. He alleges that Diddy exercised complete

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12:04

Clayton Howard Blasts Diddy AND Cassie Ventura In An...

The Diddy Diaries ·

2025/10/26

Clayton Howard, a former male escort and frequent participant in Diddy’s private sex parties known as “freak-offs,” has filed a lawsuit accusing both Sean “Diddy” Combs and Cassie Ventura of sex trafficking, coercion, and abuse. According to his claims, he was recruited to perform sex acts under the guise of high-end parties, only to find himself drugged, manipulated, and transported across state lines for increasingly degrading and violent encounters. He alleges that Diddy exercised complete

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11:24

Clayton Howard Blasts Diddy AND Cassie Ventura In An...

The Diddy Diaries ·

2025/10/25

Clayton Howard, a former male escort and frequent participant in Diddy’s private sex parties known as “freak-offs,” has filed a lawsuit accusing both Sean “Diddy” Combs and Cassie Ventura of sex trafficking, coercion, and abuse. According to his claims, he was recruited to perform sex acts under the guise of high-end parties, only to find himself drugged, manipulated, and transported across state lines for increasingly degrading and violent encounters. He alleges that Diddy exercised complete

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13:46

Allegations That 'Victim 3' Was Paid Off And Suge...

The Diddy Diaries ·

2025/10/25

Gene Deal, Sean "Diddy" Combs's former bodyguard, alleged in a recent interview that Combs paid his ex-girlfriend Gina Huynh approximately $2 million, along with providing her housing and educational support, to dissuade her from testifying in his federal sex trafficking and racketeering trial. Deal claimed that Huynh, believed to be "Victim 3" in the indictment, became a "hostile witness" after accepting these benefits, leading to her disappearance from the witness list. Despite being subpoenaed,

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16:42

Will Prince Andrew Face Legal Consequences Amid The...

The Diddy Diaries ·

2025/10/25

The UK’s Metropolitan Police Service (Met) is now “actively looking” into fresh allegations that Prince Andrew allegedly used a taxpayer-funded police bodyguard to obtain the U.S. Social Security number and date of birth of his accuser, Virginia Giuffre — apparently to dig up “dirt” on her. These new allegations arise from leaked emails and Giuffre’s recently published posthumous memoir, and they have reignited calls for a full criminal inquiry in the UK after previous investigations by the Met

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13:19

Will Prince Andrew Face Legal Consequences Amid The...

The Diddy Diaries ·

2025/10/25

The UK’s Metropolitan Police Service (Met) is now “actively looking” into fresh allegations that Prince Andrew allegedly used a taxpayer-funded police bodyguard to obtain the U.S. Social Security number and date of birth of his accuser, Virginia Giuffre — apparently to dig up “dirt” on her. These new allegations arise from leaked emails and Giuffre’s recently published posthumous memoir, and they have reignited calls for a full criminal inquiry in the UK after previous investigations by the Met

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26:52

Mega Edition: Prince Andrew And His BBC Interview Get...

The Diddy Diaries ·

2025/10/25

In 2024, Netflix announced Scoop, a dramatization of Prince Andrew’s disastrous 2019 BBC Newsnight interview with Emily Maitlis, which infamously backfired and forced him to withdraw from royal duties. The film, directed by Philip Martin and based on BBC producer Sam McAlister’s memoir Scoops: Behind the Scenes of the BBC’s Most Shocking Interviews, explores how the interview was negotiated and produced behind the scenes. Gillian Anderson stars as Emily Maitlis, while Rufus Sewell portrays Prince

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31:58

Mega Edition: An Inside Look At The BBC Interview...

The Diddy Diaries ·

2025/10/25

Sam McAlister — former BBC Newsnight producer and author of Scoops: Behind the Scenes of the BBC’s Most Shocking Interviews — has given extensive behind-the-scenes commentary on how the infamous interview with Prince Andrew, Duke of York came to be. She recounts how her original approach was for a routine charity-profile, but as the scandal involving Jeffrey Epstein intensified, she persuaded the palace to agree to a sit-down that would include “the news issues that were pertinent” — including

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31:28

Mega Edition: Prince Andrew Was Initially Pleased...

The Diddy Diaries ·

2025/10/25

After his disastrous BBC Newsnight interview aired on November 16, 2019, Prince Andrew initially tried to defend both his performance and his decision to do it. He reportedly believed the interview had gone “very well” and that it would clear the air about his association with Jeffrey Epstein. His public statement that followed expressed “sympathy for all those affected by Epstein’s behavior” but maintained his innocence, repeating that he had “no recollection” of ever meeting Virginia Roberts

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55:43

Mega Edition: Prince Andrew And The Humiliating...

The Diddy Diaries ·

2025/10/25

The infamous photograph showing Prince Andrew with his arm around Virginia Giuffre (then Roberts), with Ghislaine Maxwell smiling in the background, became one of the most scrutinized pieces of evidence in the Epstein scandal. Giuffre has maintained that the photo, taken in 2001 at Maxwell’s London townhouse, is proof she met the prince and was trafficked to him as a teenager. Andrew and his lawyers have long disputed its authenticity, suggesting the image may have been doctored or that he has “no

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48:00

Mega Edition: How Jeffrey Epstein Used Prince...

The Diddy Diaries ·

2025/10/25

Jeffrey Epstein’s relationship with Prince Andrew was a calculated social maneuver designed to elevate Epstein’s standing among the world’s elite. By befriending the Duke of York — a senior member of the British royal family — Epstein gained access to circles of wealth and influence that would have otherwise been closed to him. The two men traveled together, attended exclusive parties, and were photographed at high-society events from New York to Palm Beach. Epstein reportedly viewed Andrew as a

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17:02

Should Diddy's Accusers Be Able To Proceed With Their...

The Diddy Diaries ·

2025/10/25

Allowing an accuser to proceed anonymously in civil lawsuits or criminal proceedings offers several advantages. It protects the individual's privacy, especially in cases involving sensitive matters like sexual assault, thereby reducing potential public scrutiny and emotional distress. Anonymity can also shield the accuser from possible retaliation or harassment, encouraging victims to come forward without fear of personal repercussions. This protection is particularly vital when the accused holds

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11:32

Cassie Ventura Files A Motion To Quash The Subpoena...

The Diddy Diaries ·

2025/10/25

In April 2025, Cassie Ventura, identified as "Victim-1" in Sean "Diddy" Combs' upcoming federal trial, filed a motion to quash a subpoena issued by Combs' legal team. The subpoena demanded access to all drafts of her memoir, personal diaries, journals, notes, and ten months of her bank statements from 2023. Ventura's attorney, Douglas Wigdor, argued that the subpoena was overly broad and lacked specificity, asserting that Combs' team failed to demonstrate the admissibility or relevance of the

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10:25

The Governments Request To Limit Cassie Ventura's...

The Diddy Diaries ·

2025/10/25

In a letter to Judge Subramanian, the Government formally requested that the court limit the defense’s cross-examination of Cassie Ventura to ensure it concludes by the end of the trial day on May 16, 2025. Prosecutors argued that the court has broad discretion to manage trial proceedings efficiently and that the defense has already had ample time to prepare and conduct its questioning. They noted that the cross-examination has been granted nearly two full trial days—already exceeding the duration

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