Timeline of Sean "Diddy" Combs' Legal Issues and Trial

Prior to 2000

• 1990: Liza Gardner alleges that Sean 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 a video of the assault.

2000s

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

• 2000 (MTV VMA after-party): A civil lawsuit later alleges Combs and Jay-Z raped a 13-year-old girl. (This lawsuit was dropped in February 2025).

• 2001: Thalia Graves alleges Combs and his head of security drugged her, bound her, and raped her, recording the incident.

• 2005: Combs sells a 50% stake in Bad Boy Records to Warner Music Group for a reported $30 million.

• From at least 2008: Prosecutors allege Sean Combs began leading a "criminal enterprise" that engaged in sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice.

2009-2018

• From at least 2009, up to and including 2018: Prosecutors allege Combs engaged in sex trafficking by force, fraud, or coercion (Victim-1) and transported individuals for prostitution.

2014

• Combs purchases a home in Holmby Hills, Los Angeles, for $40 million.

2016

• Surveillance video (obtained by CNN in May 2024) shows Sean Combs physically assaulting Cassie Ventura.

2018

• Tanea Wallace describes seeing minors "dressed up like Harajuku Barbies, red lipstick, looking like real sexy" at a Diddy party.

2019

• Forbes estimates Combs' personal wealth at $740 million.

2021-2024 (approx.)

• "Jane" (pseudonym), a former girlfriend, dates Combs until his arrest in 2024 and alleges she was coerced into sex sessions with male escorts.

Late 2022 - March 2024

• Brendan Paul works as Combs' personal assistant.

January 2024

• Combs sells his share in the DeLeón tequila brand for $200 million.

November 2023

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

• November 17, 2023: Cassie Ventura settles her lawsuit against Sean Combs. (She later testifies in May 2025 that this settlement was for $20 million).

• November 23, 2023: Two more lawsuits are filed: Liza Gardner's allegations against Combs and Aaron Hall, and Joi Dickerson-Neal's allegations against Combs.

• November 27, 2023: Combs leaves his role at Revolt Media.

• November 28, 2023: U.S. Magistrate Judge Robyn Tarnofsky denies Combs bail, citing "compelling evidence of Combs’s propensity for violence" and risk of witness tampering.

December 2023

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

• December (various dates): Macy's begins removing Diddy's Sean John brand; other brands cut ties with Combs' e-commerce business; a reality TV show about Diddy's family is pulled.

• December 8, 2024: Combs, along with Jay-Z, are accused in a civil lawsuit of raping a 13-year-old girl at an MTV VMA after-party in 2000.

• December (various dates): Combs is accused of raping and sexually assaulting three men, committing sexual battery against a former male employee, and drugging and sexually assaulting a woman in separate lawsuits.

January 2024

• January 12, 2024: Combs reportedly does not attend the 2024 Grammys.

February 2024

• Rodney Jones accuses Combs of forcing him to engage in sex acts with sex workers and sex trafficking.

March 2024

• March 26, 2024: Federal agents raid two of Combs' properties in Los Angeles and Miami, seizing items including drugs, firearms, baby oil, and lingerie.

September 2024

• September 10, 2024: Dawn Richard files a lawsuit against Combs, alleging sex trafficking, sexual assault, sexual battery, false imprisonment, and confirming she witnessed claims in Ventura's lawsuit.

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

• September 17, 2024: Combs pleads not guilty in his first court appearance in Manhattan federal court. Judge Tarnofsky denies bail, ordering him to remain in federal custody.

• September 18, 2024: A second judge, Andrew L. Carter Jr., denies Combs bail again due to concerns about witness threats and intimidation, 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 27, 2024: A Florida model files a lawsuit (as Jane Doe) alleging Combs drugged, sexually assaulted, and impregnated her.

October 2024

• October 1, 2024: Approximately 120 additional sexual assault lawsuits are reported to be filed against Combs.

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

• October 14, 2024: Sean Combs is accused of sexual assault and rape in new lawsuits, including six new accusers, one claiming assault at a White Party.

• October 21, 2024: Seven new lawsuits are filed against Combs, one alleging he drugged and raped a 13-year-old girl.

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

November 2024

• November 12, 2024: Ray J claims high-profile celebrities are "reaching out to victims" and offering money for silence in "The Downfall of Diddy: Inside the Freak-Offs."

• November 15, 2024: Prosecutors claim Combs attempted to "corruptly influence witness testimony" and manipulate potential jury members.

December 2024

• December 8, 2024: A civil lawsuit accuses Combs and Jay-Z of raping a 13-year-old girl in 2000.

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

• December 24, 2024: A former male employee sues Combs for sexual battery.

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

January 2025

• January 13, 2025: A new lawsuit claims Combs raped a 16-year-old babysitter in September 2000.

• January 14, 2025: Combs' lawyers submit a letter demanding prosecutors produce "freak off" videos, claiming they show consensual sex.

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

• January 30, 2025: Combs is reportedly transported from prison to Brooklyn Hospital Center for an MRI due to knee pain.

February 2025

• February 6, 2025: Rapper Kanye West tweets "Free Puff" and continues to express support for Combs.

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

• February 18, 2025: Combs' lawyers ask a judge to dismiss a transportation to engage in prostitution charge, arguing it has racist origins and Combs is being singled out.

March 2025

• March 6, 2025: Prosecutors file a new indictment against Combs, accusing him of maintaining control over employees through threats and force, and forcing one employee into sex acts.

• March 14, 2025: Combs pleads not guilty to the new indictment. Jury selection is set for May 5, and tentative trial date for May 12.

• March 24, 2025: U.S. District Judge J. Paul Oetken rules Rodney Jones' sex trafficking allegations can proceed, but dismisses Racketeer Influenced and Corrupt Organizations Act claims.

April 2025

• April 4, 2025: Prosecutors file another superseding indictment against Combs, adding two charges: an additional sex trafficking count and another transportation to engage in prostitution count, concerning "Victim-2."

• April 18, 2025: Combs' lawyers' bid to delay the trial for two months is denied.

May 2025

• May 5, 2025: Jury selection for Combs' sex trafficking and racketeering trial begins in the Federal District Court in Lower Manhattan. Some protestors wear "Free Puff" or "Free $Diddy" shirts, with one claiming to be paid $20/hour.

• May 12, 2025: Opening statements and witness testimony begin, with Cassie Ventura as the first prosecution witness.

• May 14, 2025: Cassie testifies about settling her civil suit for $20 million.

• May 22, 2025: Judge Subramanian states the trial should "wrap up" by July 4.

• May 30, 2025: President Donald Trump indicates he would "look at the facts" regarding a potential pardon for Combs.

June 2025

• June 23, 2025: Diddy's defense lawyers announce they won't call any witnesses. Prosecutors had called 34.

• June 24, 2025: Prosecution rests its case. Testimony in the trial officially ends after six weeks of evidence.

• June 26, 2025: Prosecutor Christy Slavik presents her closing arguments, describing Combs as running a "criminal enterprise."

• June 27, 2025: Defense attorney Marc Agnifilo delivers a four-hour closing argument, asserting Combs' innocence and mocking the prosecution's case.

July 2025

• July 4, 2025: Judge Subramanian's target date for the trial to conclude.

Cast of Characters

Principal Figures:

• Sean "Diddy" Combs (also known as Puff Daddy, P. Diddy, PD, Love): American rapper, record executive, and founder of Bad Boy Records. He is the central figure in the numerous civil lawsuits and federal criminal charges related to sex trafficking, racketeering, and other alleged misconduct. He has pleaded not guilty to all criminal charges, claiming all encounters were consensual.

• Cassie Ventura (full name Casandra Elizabeth Ventura Fine): R&B singer and former long-term girlfriend of Sean Combs. She filed a high-profile civil lawsuit against Combs in November 2023, alleging rape, trafficking, and physical assault over a decade. She settled this lawsuit for $20 million and later testified against Combs in his criminal trial.

• "Jane" (pseudonym): A former girlfriend of Sean Combs (dated from 2021 until his arrest in 2024). She testified that Combs coerced her into participating in "freak-offs" with male escorts and regularly texted for cash.

Key Witnesses and Accusers (in criminal trial or civil suits):

• Brendan Paul: Sean Combs' former personal assistant (late 2022-March 2024). He was arrested for cocaine possession in Miami (March 2024) and testified in the trial about buying drugs for Combs and the "freak-offs," asserting loyalty to the mogul.

• Dawn Richard: Singer and former member of Diddy-backed groups Danity Kane and Dirty Money. She filed a lawsuit against Combs in September 2024 and testified in the trial that Combs was "frequently" violent with Cassie and threatened her life.

• Kerry Morgan: Cassie Ventura's former best friend. She testified about Combs' mood swings, an instance where he choked her, and two occasions she allegedly saw him beat Cassie.

• Regina Ventura: Cassie Ventura's mother. She testified about feeling "physically sick" when her daughter told her Combs threatened to release explicit sex tapes. She also took out a $20,000 home equity loan after sex tape threats, which was returned within 24 hours.

• "The Punisher": A male exotic dancer who testified about between eight and twelve sexual encounters with Combs and Cassie, describing them as a "fetish type thing" and noting Cassie would often look at Combs for cues.

• Kid Cudi: Rapper who briefly dated Cassie Ventura. He testified that Combs broke into his home, "messed with" his dog, and opened his Christmas presents.

• Rodney Jones: Former producer for Combs. He sued Combs in February 2024, accusing him of forcing him to engage in sex acts and sex trafficking. His sex trafficking allegations were allowed to proceed in March 2025.

• Liza Gardner: Accused Combs and Aaron Hall of sexual assault in 1990 in a lawsuit filed in November 2023.

• Joi Dickerson-Neal: Accused Combs of drugging and sexually assaulting her in 1991 and sharing the video of the assault in a lawsuit filed in November 2023.

• Jane Doe (December 2023 lawsuit): Alleged she was gang-raped by Combs, Harve Pierre, and a third assailant as a teenager.

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

• Jane Doe (Florida model, September 2024 lawsuit): Alleged Combs drugged, sexually assaulted, and impregnated her, and that Yung Miami pressured her to have an abortion.

• Woman (January 2025 lawsuit): Claimed Combs sexually assaulted her when she was a 16-year-old babysitter in September 2000.

• Unnamed male sex worker: Testified about encounters with Combs and Cassie, and stated he was present when Combs was violent.

Legal and Political Figures:

• Marc Agnifilo: Sean Combs' defense attorney. He argued for Combs' innocence and mocked the prosecution's case in closing arguments.

• Emily Johnson: Prosecutor in Combs' trial. She described Combs as running a "criminal enterprise."

• Christy Slavik: Prosecutor who presented closing arguments, asking the jury to imagine Cassie's position and detailing the alleged indiscretions.

• Brian Steele: Defense attorney, known for defending rapper Young Thug, who cross-examined Brendan Paul.

• U.S. District Judge J. Paul Oetken: Judge who ruled on Rodney Jones' claims.

• U.S. District Judge Arun Subramanian: Judge presiding over Combs' criminal trial. He oversees jury selection and has made rulings regarding bail and trial schedule.

• U.S. Magistrate Judge Robyn Tarnofsky: Judge who initially denied Combs bail in September 2024.

• U.S. Special Agent DeLeassa Penland: Testified for the prosecution, focusing on travel logistics related to Cassie Ventura and "freak-offs."

• Donald Trump: Former (and potential future) President of the United States. Stated he would "look at the facts" regarding a potential pardon for Sean Combs.

• Donald Trump Jr.: Son of Donald Trump. Spread a conspiracy theory linking celebrity endorsements for Kamala Harris to Diddy's parties.

• Kamala Harris: Vice President of the United States. Baselessly linked by Donald Trump Jr. to a blackmail scheme involving Diddy's parties and celebrity endorsements.

Other Notable Mentions:

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

• Harve Pierre: Former president of Bad Boy Records, accused by a Jane Doe of gang-raping her with Combs in New York.

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

• Yung Miami: Rapper and Combs' then-girlfriend, alleged by a Florida model to have pressured her to have an abortion.

• Ray J: Claims high-profile celebrities are "reaching out to victims" and offering money for silence.

• Tanea Wallace: Described seeing minors at a 2018 Diddy party "dressed up like Harajuku Barbies."

• Elon Musk: Billionaire, commented on the Diddy scandal before the election, urging people not to trust Jennifer Lopez's opinion because she didn't "warn" people against Combs.

• Jennifer Lopez: Singer and actress, endorsed Kamala Harris for president, prompting criticism from Elon Musk.

• Kanye West: Rapper, expressed support for Combs, tweeting "Free Puff" and calling him a "hero" and "idol," linking allegations to a Hollywood "elite" conspiracy.

• Christian Combs: Diddy's son, seen in a video call with Kanye West, captioned to support sons with incarcerated fathers.

• Misa Hylton: Mother of Combs’ eldest son Justin Combs, attended the trial in support of Combs.

• Vado: Rapper, attended the trial with Misa Hylton and is involved in a lawsuit with Mary J. Blige.

• Mary J. Blige: Singer, involved in a lawsuit with Vado regarding a withheld album and management.

• Elie Aoun: Forensic and addictions psychiatrist, mentioned by MIMS as a witness the defense should have called.

• Kelley: Legal commentator who found Regina Ventura's testimony compelling.

• MIMS: Host of "Make it Make Sense," expressed concern that the jury might not see Combs' former girlfriends as victims.

• Shakur: Believes the repeated showing of a violent video might have lost its shock value.

• Shapiro: Defense attorney who argued that Cassie enjoyed the sexual activity and did not feel coerced.

• Khorram: A recipient of texts from Jane asking for cash from Combs' safe, and from Combs requesting drugs.