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Detailed Timeline of Main Events

  • Writer: Cassian Creed
    Cassian Creed
  • Jun 11
  • 8 min read

1990-1991:

  • 1990: Liza Gardner alleges that Sean "Diddy" Combs and Guy's Aaron Hall sexually assaulted her and her friend.

  • 1991: Joi Dickerson-Neal alleges that Combs drugged and sexually assaulted her and shared the video of her sexual assault.

2000s:

  • September 2000: A woman claims Combs sexually assaulted her when she was a 16-year-old babysitter.

  • December 2000: Combs and Jay-Z are accused in a civil lawsuit of raping a 13-year-old girl at an MTV Video Music Awards after-party (lawsuit dropped in February 2025).

  • 2001: Thalia Graves alleges Combs and his head of security drugged her, bound her, raped her, and recorded the incident when she was 25.

2012-2023 (Cassie Ventura's Allegations):

  • November 16, 2023: Cassie Ventura files a lawsuit accusing Sean "Diddy" Combs of rape, trafficking, and physical assault over a ten-year period.

  • November 17, 2023: Cassie settles her lawsuit with Combs.

  • November 23, 2023: Two more lawsuits are filed against Combs by Liza Gardner and Joi Dickerson-Neal.

  • December 6, 2023: A Jane Doe files a lawsuit alleging she was gang-raped by Combs, Harve Pierre, and a third assailant in 2000 when she was a teenager.

  • December 2023: Macy's begins removing Diddy's Sean John brand. Diddy leaves Revolt Media role. Numerous brands cut ties with Diddy's e-commerce business. A reality TV show about Diddy's family is pulled. The Recording Academy evaluates Diddy's Grammy invitation.

  • Late 2023: Radio stations like Boston's Jam'n 94.5 and California’s 93.5 KDAY pull Diddy's music.

2024:

  • February 2024: Rodney Jones accuses Combs of sexual assault in a lawsuit.

  • March 26, 2024: Federal agents raid multiple properties of Sean "Diddy" Combs in Los Angeles and Miami, seizing electronics.

  • April 14, 2024: Kesha changes "Tik Tok" lyrics to "F*** P. Diddy" during Coachella performance.

  • May 17, 2024: Surveillance video from 2016 showing Diddy physically assaulting Cassie Ventura is obtained and released by CNN.

  • May 19, 2024: Diddy admits to beating Cassie Ventura and apologizes, calling his actions "inexcusable."

  • May 2024: Streaming activity and radio airplay for Diddy's music drop. Peloton cuts ties with Diddy.

  • June 7, 2024: Howard University revokes Diddy's honorary degree and terminates a $2 million gift and pledge agreement.

  • June 16, 2024: Diddy returns the key to NYC after a request from Mayor Eric Adams.

  • June 28, 2024: "Diddy Day" in Miami Beach is cancelled.

  • September 10, 2024: Dawn Richard files a lawsuit against Combs alleging sex trafficking, sexual assault, and more.

  • September 16, 2024: Sean "Diddy" Combs is arrested by U.S. Homeland Security investigators in Manhattan after a grand jury indictment.

  • September 17, 2024: Combs pleads not guilty to all federal criminal charges in his first court appearance in Manhattan. U.S. Magistrate Judge Robyn Tarnofsky denies bail.

  • September 18, 2024: A second judge, Andrew L. Carter Jr., denies Diddy bail due to concerns about witness threats, despite a $50 million bond offer. Combs remains incarcerated at the Metropolitan Detention Center in Brooklyn.

  • September 24, 2024: Thalia Graves files a lawsuit against Combs.

  • September 25, 2024: Netflix announces the development of a documentary miniseries about the allegations, "Diddy Do It," executive produced by 50 Cent.

  • September 27, 2024: A Florida model files a lawsuit as a Jane Doe, alleging Combs drugged, sexually assaulted, and impregnated her.

  • October 1, 2024: Over 100 additional sexual assault lawsuits are reported to be filed against Combs.

  • October 10, 2024: Diddy's trial date for sex crimes charges is set for May 2025.

  • October 14, 2024: Six new accusers sue Sean Combs, including a teen claiming assault at a White Party.

  • October 21, 2024: Seven new lawsuits are filed against Sean Combs, including allegations of drugging and raping a 13-year-old girl.

  • October 29, 2024: Sean "Diddy" Combs is accused in new lawsuits of sexually assaulting 10- and 17-year-old boys.

  • December 8, 2024: Jay-Z is accused in a civil lawsuit of raping a 13-year-old girl in 2000 along with Sean "Diddy" Combs.

  • December 13, 2024: Three men accuse Sean "Diddy" Combs of rape and sexual assault in new lawsuits.

  • December 24, 2024: Sean "Diddy" Combs is sued by a former male employee for sexual battery.

  • December 26, 2024: A woman claims she was "lured" to Sean "Diddy" Combs' party through a radio contest and drugged and sexually assaulted.

2025:

  • January 3, 2025: Peacock releases a trailer for "Diddy: The Making of a Bad Boy" documentary.

  • January 13, 2025: Sean Combs is sued by a woman who claimed he sexually assaulted her when she was a 16-year-old babysitter in September 2000.

  • January 14, 2025: Peacock's "Diddy: The Making of a Bad Boy" documentary is released.

  • January 28, 2025: Investigation Discovery releases "The Fall of Diddy," a 5-part documentary series.

  • January 31, 2025: Prosecutors add two new victims to the Sean Combs case.

  • February 7, 2025: Kanye West tweets "Free Puff" and launches a Sean John collaboration to support Diddy, urging Trump to pardon him.

  • February 15, 2025: The lawsuit accusing Sean "Diddy" Combs and Jay-Z of raping a 13-year-old girl is dropped.

  • February 21, 2025: Diddy's lawyer quits, as he loses part of his legal team.

  • April 18, 2025: A bid by Combs's lawyers to delay the trial for two months is denied due to late submission.

  • May 5, 2025: Diddy's federal sex crimes trial begins with jury selection in Lower Manhattan.

  • May 12, 2025: Opening statements and witness testimony begin in Diddy's trial, with Cassie Ventura being the first witness for the prosecution.

  • May 13, 2025: Cassie Ventura takes an oath before testifying in Manhattan federal court.

  • May 14, 2025: It is revealed that Cassie Ventura settled her lawsuit against Sean Combs for $20 million.

  • May 22, 2025: Judge Arun Subramanian states the trial should "wrap up" by July 4. U.S. Attorney Maurene Comey arrives for the trial.

  • June 7, 2025: Diddy's legal team files a letter arguing prosecutorial misconduct and knowingly presenting false testimony, requesting a mistrial.

  • June 10, 2025: Judge Arun Subramanian denies Diddy's second request for a mistrial regarding Bryana Bongolan's testimony. Sean "Diddy" Combs' ex-girlfriend, "Jane," testifies and is cross-examined, discussing "hotel nights" and Diddy's polyamorous nature and drug use.

  • June 11, 2025 (Day 20 of trial): "Jane" continues cross-examination, detailing "hotel nights," drug use, and Diddy's controlling behavior. She reveals Diddy is still paying her rent. Prosecutors request a juror be dismissed due to "lack of candor."

Cast of Characters

Principle Accused:

  • Sean "Diddy" Combs (aka Puff Daddy, P. Diddy, PD, Love): A prominent American rapper, record executive, and music mogul. He is currently facing a federal criminal trial on charges of sex trafficking, racketeering, and transportation to engage in prostitution, to which he has pleaded not guilty. He also faces numerous civil lawsuits alleging sexual misconduct, assault, and abuse dating back to 1990.

Alleged Victims / Witnesses:

  • Cassie Ventura (Cassandra Ventura Fine): Diddy's former girlfriend and a singer. She filed a civil lawsuit against Combs in November 2023, alleging rape, trafficking, and physical assault over a decade. She settled the lawsuit for $20 million and was the first witness to testify for the prosecution in Diddy's federal trial in May 2025.

  • Bryana Bongolan (Bana): A friend of Cassie Ventura's. She testified against Diddy, claiming he held her over a 17-story balcony in Los Angeles in September 2016. Her testimony has been a point of contention in the trial, with Diddy's defense team claiming she perjured herself.

  • "Jane": An anonymous former girlfriend and alleged victim of Sean "Diddy" Combs, currently testifying under a pseudonym in his federal trial. She describes "hotel nights" involving sex with male escorts, Diddy's alleged drug use, and his controlling behavior. She claims to still love Diddy and that he is paying for her lawyer and rent.

  • Liza Gardner: Accused Combs and Guy's Aaron Hall of sexual assault in 1990.

  • Joi Dickerson-Neal: Alleged in a 2023 lawsuit that Combs drugged and sexually assaulted her in 1991 and shared the video.

  • Dawn Richard: A former member of "Making the Band," she filed a lawsuit against Combs in September 2024 alleging sex trafficking, sexual assault, and more, and confirmed she was a witness to Cassie Ventura's claims.

  • Thalia Graves: Filed a lawsuit in September 2024 alleging Combs and his head of security drugged, bound, and raped her in 2001, recording the incident.

  • Anonymous Florida Model (Jane Doe): Filed a lawsuit in September 2024 alleging Combs drugged, sexually assaulted, and impregnated her.

Legal and Court Figures:

  • Maurene Comey: Lead prosecutor and U.S. Attorney for the government's case against Sean "Diddy" Combs.

  • Nicole Westmoreland: An attorney for Sean "Diddy" Combs. She countered Bryana Bongolan's testimony with hotel records.

  • Teny Geragos: A criminal defense lawyer for Sean "Diddy" Combs. She handled the cross-examination of "Jane," attempting to portray her as a willing participant or a "disgruntled girlfriend."

  • Judge Arun Subramanian: The U.S. District Judge overseeing Sean "Diddy" Combs' federal sex crimes trial. He has denied Diddy's requests for a mistrial.

  • David Seltzer: An attorney who provided commentary to Fox News Digital on the trial, stating Jane's testimony shows Diddy is a "sexual deviant" but doesn't necessarily prove the government's case.

  • Neahma Rahmani: A former federal prosecutor who provided commentary to Fox News Digital, stating the case "comes down to coercion versus consent."

  • Lawrence Zimmerman: A criminal defense attorney and panelist on Fox News who provided legal commentary on the trial, including aspects of jury behavior and the definition of sex trafficking.

  • Serena Townsen: A criminal defense attorney and former prosecutor, also a panelist on Fox News, providing legal analysis, particularly on cross-examination strategy and jury nullification.

  • Dr. Dawn Hughes: A forensic psychologist whose recall to the stand was denied by Judge Subramanian.

  • U.S. Magistrate Judge Robyn Tarnofsky: Denied Combs bail in his first court appearance.

  • Judge Andrew L. Carter Jr.: Denied Combs bail for a second time, citing concerns about witness threats.

Other Individuals Mentioned:

  • Frank Black: An alias allegedly used by Sean Combs at the Trump International Hotel in New York in September 2016.

  • Paul, Don, Cabral, "The Italian": Male escorts or entertainers allegedly involved in Diddy's "hotel nights."

  • Gina: Another of Diddy's female partners, mentioned by "Jane" as receiving "beautiful things" and being allowed to post on social media.

  • KK (Christina Cororm): Diddy's former chief of staff, mentioned in texts by "Jane."

  • Ryan Leslie: Allegedly Cassie Ventura's first boyfriend, who dated her for three years and is suggested to have introduced her to Diddy.

  • Aaron Hall: Member of the group Guy, accused alongside Combs by Liza Gardner of sexual assault in 1990.

  • Harve Pierre: Former president of Bad Boy Records, accused alongside Combs of gang-raping a Jane Doe in 2000.

  • Yung Miami: Diddy's then-girlfriend, who allegedly pressured an anonymous Florida model to have an abortion.

  • Jay-Z: Accused alongside Combs in a civil lawsuit of raping a 13-year-old girl in 2000 (lawsuit later dropped).

  • Rodney Jones: Former producer for Sean Combs, who accused him of sexual assault in February 2024.

  • Kanye West: Supported Diddy by tweeting "Free Puff" and launching a Sean John collaboration in February 2025, urging Donald Trump to pardon him.

  • 50 Cent: Executive producer of the Netflix documentary "Diddy Do It," stating proceeds will go to victims of sexual assault and rape.

  • Al B. Sure!: Singer who spoke on camera in the Peacock documentary "Diddy: The Making of a Bad Boy" about Kim Porter.

  • Kobe Bryant, Shaquille O'Neal, Michael Jordan: Basketball stars whose names were used for nicknames by "Jane" and Diddy during "hotel nights" (the Trifecta).

Commentators/Reporters:

  • Joshua Rhett Miller: Newsweek chief investigative reporter, author of one of the sources.

  • Sean Gunby: Host of "The Podcast With Soul," expressed skepticism about Bryana Bongolan's testimony and believes prosecutors lost credibility.

  • Tracy Wright, Lauryn Overhultz, Maria Paronich: Fox News reporters, authors/co-authors of some of the sources.

  • CB Cotton: Fox News correspondent.

  • Merlin Spies, Maria Chavez, Bella Reyes, Legal Code, Morin Grogan, Richard Esaw, Denise Lopez: Reddit users and "super chat" question askers in the reported legal commentary.

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NotebookLM can be inaccurate; please double check its responses.

 
 
 

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