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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

18:58

Epstein Survivors Hit Bank of America And Bank Of NY...

The Diddy Diaries ·

2025/10/16

A woman, filing under the pseudonym Jane Doe, has sued Bank of America and Bank of New York Mellon in Manhattan federal court, accusing them of playing a financial role in enabling Jeffrey Epstein’s sex trafficking operation. She alleges that Epstein and his associates used her Bank of America account—opened at the direction of Epstein’s accountant—as a conduit for rent payments, payroll for a “sham company,” and other transfers. The complaint claims the banks ignored obvious red flags, failed to

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23:14

Mega Edition: Diddy's Dash To Reveal The Identities...

The Diddy Diaries ·

2025/10/16

In this filing, Sean Combs opposes the government’s motion seeking permission to withhold the identities of certain witnesses in the civil RICO case, arguing that such secrecy is unjustified and prejudicial. Combs’ legal team contends that the government’s vague claims of witness safety concerns lack any factual foundation or evidence of real threats from Combs or his legal team. They argue that the government's request to conceal witness identities, even during the early stages of discovery,

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21:57

The Mega Edition: Diddy And The Reply Brief Filed...

The Diddy Diaries ·

2025/10/16

In the Appellant's Reply Brief for United States v. Sean Combs, case number 24-CR-542 (AS), the defense challenges the district court's decisions on multiple grounds. First, they argue that the court erred in denying the motion to suppress evidence obtained during a warrantless search, asserting that this violated Combs' Fourth Amendment rights. Second, the defense contends that the court improperly admitted hearsay statements under the co-conspirator exception, allowing prejudicial evidence to

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10:58

Diddy Gets Slammed With Suffocating Post Release...

The Diddy Diaries ·

2025/10/16

After his sentencing, Sean “Diddy” Combs will face extremely restrictive conditions during a five-year supervised release period following his roughly 50-month prison term. These conditions include mandatory outpatient treatment for both substance abuse and mental health, adherence to all prescribed medications, and enrollment in a domestic violence intervention program. He is also permanently barred from owning or possessing any firearms or destructive devices. The supervision is designed to

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25:55

Mega Edition: Diddy And The First Bail Pitch (10/16/25)

The Diddy Diaries ·

2025/10/16

Sean "Diddy" Combs proposed a $50 million bail package in an attempt to secure his release from federal custody while awaiting trial on charges including sex trafficking and racketeering. His legal team offered a combination of assets as collateral, including his $48 million mansion on Miami's Star Island and an additional $2 million covered by his mother's home.Combs was also willing to submit to GPS monitoring, travel restrictions limited to Florida, New York, and New Jersey, and the surrender of

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30:10

The Mega Edition: Reign Doe's Lawsuit Against...

The Diddy Diaries ·

2025/10/16

The Mega condenses the lawsuits against Sean "Diddy" Combs into one powerful, comprehensive episode. From allegations of misconduct to claims of power abuse, this episode brings together the transcripts from Diddy's second bail attempt in a single, unfiltered narrative. John Doe, a former employee of Reign, made serious allegations against Sean Combs, detailing instances of sexual harassment, coercion, and a hostile work environment. Doe claims that Combs engaged in inappropriate behavior during

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31:05

Mega Edition: Diddy And the 3rd Superseded...

The Diddy Diaries ·

2025/10/16

The superseding indictment expands the timeline of Combs' alleged criminal activities, now spanning from 2004 to 2024, and introduces additional charges. Combs is accused of operating a criminal enterprise involving racketeering, sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice. The indictment details that Combs allegedly coerced multiple women, identified as Victim-1, Victim-2, and Victim-3, into engaging in commercial sex acts through force, fraud, and

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32:54

The Mega Edition: Mass Security John Doe And His...

The Diddy Diaries ·

2025/10/16

A recent lawsuit filed by an anonymous plaintiff, identified as John Doe, claims that while employed by MASS Security at Sean "Diddy" Combs' renowned 2006 Hamptons White Party, he experienced a traumatic assault. According to the suit, Doe was given an alcoholic beverage by Combs that he later suspected was drugged. He alleges that after feeling unwell and disoriented, Combs restrained him and assaulted him inside a van. This claim is part of a larger wave of new lawsuits against Combs, which

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10:47

Diddy Looks To Shake Off The Lawsuit Filed By Shante...

The Diddy Diaries ·

2025/10/16

The Combs Defendants assert that Plaintiff’s complaint fails on multiple legal grounds and should be dismissed. First, they argue that no plausible claim is alleged under Rule 12(b)(6): the Complaint lacks sufficient factual allegations to meet the heightened pleading standard for fraud, defamation, RICO claims, or negligence. They contend Plaintiff offers nothing more than conclusory statements and unsupported legal labels, without demonstrating the required “who, what, when, where, and how” of

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11:15

Cassie Ventura Testifies Against Diddy Using Her Real...

The Diddy Diaries ·

2025/10/16

Cassie Ventura, the former partner of Sean "Diddy" Combs, has chosen to testify under her real name in his upcoming federal trial, where he faces charges including racketeering conspiracy, sex trafficking, and transportation to engage in prostitution. Identified in court documents as "Victim-1," Ventura's decision contrasts with three other alleged victims who have requested to remain anonymous due to concerns about media harassment and personal safety. Prosecutors have filed motions to allow these

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15:24

Diddy Beat The Most Serious Criminal Charges But He...

The Diddy Diaries ·

2025/10/16

Sean "Diddy" Combs has been convicted on two federal counts of transporting individuals for prostitution, stemming from a high-profile trial that concluded on July 2, 2025. The jury acquitted him of more severe charges, including sex trafficking and racketeering. Despite the convictions, Combs faces a maximum sentence of 20 years, though he is expected to serve a reduced term of 15–21 months, with nearly 10 months already served. He remains incarcerated at the Metropolitan Detention Center in

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14:25

Nikki Glaser And Her Diddy Jokes At The Golden Globe...

The Diddy Diaries ·

2025/10/15

At the 2025 Golden Globe Awards, host Nikki Glaser delivered a sharp monologue that included pointed jokes about Sean "Diddy" Combs, who is currently facing serious legal charges. Glaser quipped that the film "Challengers" was "more sexually charged than Diddy's credit card," referencing allegations about his notorious parties. She also remarked that the after-party wouldn't be as lively without Diddy's presence, alluding to his current incarcerationIn a subsequent interview on "The Howard Stern

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11:43

Jeffrey Epstein And The Meeting At 10 Downing Street...

The Diddy Diaries ·

2025/10/15

Newly released documents from the UK National Archives show that former Prime Minister Tony Blair met Jeffrey Epstein on May 14, 2002, at 10 Downing Street. The meeting was reportedly arranged at the behest of Peter Mandelson, who lobbied Blair’s staff—particularly chief of staff Jonathan Powell—by describing Epstein as “safe” and a “friend” with extensive international connections. A briefing memo prepared for Blair characterized Epstein as a wealthy financial adviser with ties to Bill Clinton and

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35:52

The Mega Edition: Diddy Moves To Deny Independent ...

The Diddy Diaries ·

2025/10/15

In the case of Jane Doe v. Sean Combs et al., the defendants have submitted a memorandum opposing the plaintiff's motion to proceed anonymously. They argue that the plaintiff has not sufficiently demonstrated the need for anonymity, as required by the factors established in Sealed Plaintiff v. Sealed Defendant. The defendants contend that the plaintiff's claims, while sensitive, do not involve matters that typically warrant anonymity, such as challenging governmental actions or involving

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33:21

The Mega Edition: Independent Jane Doe And Her...

The Diddy Diaries ·

2025/10/15

In October 2024, a 29-year-old independent music artist filed a lawsuit against Sean "Diddy" Combs, alleging that he raped her during a December 2022 party in New York City. According to the complaint, the artist attended the event to network within the music industry. She claims that Combs invited her to a private area, where she was given a drink that caused her to feel disoriented. The lawsuit alleges that Combs then sexually assaulted her while she was incapacitated. After the incident, the

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12:48

Grace O'Marcaigh's Diddy/Christian Combs Lawsuit Has...

The Diddy Diaries ·

2025/10/15

A judge recently dismissed the civil lawsuit filed by Grace O’Marcaigh against Diddy (Sean “Diddy” Combs) and his son Christian, which alleged that Christian sexually assaulted her aboard a yacht chartered by his father. O’Marcaigh’s case had accused Diddy of aiding and abetting the alleged assault—claiming he created a permissive, “debauchery” environment and bore responsibility for oversight. But the dismissal indicates the court found her claims insufficient: the complaint did not include enough

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30:56

The Mega Edition: Diddy And His Fellow Travelers And...

The Diddy Diaries ·

2025/10/15

Sean "Diddy" Combs has collaborated with many influential figures in the music industry over the years. Here’s an update on some of his closest music industry associates:L.A. Reid: The music executive and co-founder of LaFace Records has been accused of sexual assault by former music executive Drew Dixon. Despite denying the allegations, Reid's motion to dismiss the lawsuit was denied in 2024, allowing the case to move forward.Russell Simmons: The Def Jam co-founder has faced multiple allegations of

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28:50

The Mega Edition: The Epstein/Diddy Similarities And...

The Diddy Diaries ·

2025/10/15

The cases of Jeffrey Epstein, R. Kelly, and Sean "Diddy" Combs, while involving different individuals, share several thematic similarities that center around allegations of sexual misconduct, abuse of power, and exploitation. Below is a comparison based on these common factors:1. Allegations of Sexual Abuse and MisconductJeffrey Epstein: Epstein was charged with running a sex trafficking ring that exploited underage girls, some as young as 14. He used his wealth and influence to recruit vulnerable

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21:11

The Mega Edition: Jay-Z And His Motion To Sanction...

The Diddy Diaries ·

2025/10/15

Defendant Shawn Carter, known as Jay-Z, has filed a motion for sanctions and dismissal of the complaint against him under Federal Rule of Civil Procedure 11, arguing that the plaintiff’s claims lack legal merit and are unsupported by factual evidence. Carter asserts that the lawsuit is frivolous and intended to harass or burden him, violating Rule 11’s requirement that legal filings be grounded in a factual and legal basis. The memorandum outlines how the plaintiff’s complaint contains baseless

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25:21

The Mega Edition: Jay-Z And His Motion To Sanction...

The Diddy Diaries ·

2025/10/15

Defendant Shawn Carter, known as Jay-Z, has filed a motion for sanctions and dismissal of the complaint against him under Federal Rule of Civil Procedure 11, arguing that the plaintiff’s claims lack legal merit and are unsupported by factual evidence. Carter asserts that the lawsuit is frivolous and intended to harass or burden him, violating Rule 11’s requirement that legal filings be grounded in a factual and legal basis. The memorandum outlines how the plaintiff’s complaint contains baseless

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