Briefing: The Sean "Diddy" Combs Trial

I. Overview of the Legal Proceedings

Sean "Diddy" Combs, also known by aliases such as Puff Daddy and P. Diddy, is currently undergoing a high-profile criminal trial in New York. The trial began with jury selection on May 5, 2025, and opening statements and witness testimony commenced on May 12, 2025. The prosecution and defense concluded their cases on June 24, 2025, with closing arguments presented on June 26 and 27, and jury deliberations expected to begin on June 30, 2025. Combs has pleaded not guilty to all criminal charges.

He was arrested by U.S. Homeland Security investigators in Manhattan on September 16, 2024, following a grand jury indictment. He has been held in detention in New York since his arrest, having been refused bail multiple times due to concerns about "compelling evidence of Combs’s propensity for violence" and a "serious risk of witness tampering."

II. Criminal Charges

Combs is facing five felony charges:

• Racketeering conspiracy

• Two counts of sex trafficking by force, fraud, or coercion

• Two counts of transportation to engage in prostitution

The initial indictment included three offenses, with two additional counts added in April 2025. Prosecutors allege that Combs "abused, threatened, and coerced women and others around him to fulfill his sexual desires, protect his reputation, and conceal his conduct." They claim he "relied on the employees, resources, and influence of the multi-faceted business empire that he led and controlled—creating a criminal enterprise whose members and associates engaged in, and attempted to engage in, among other crimes, sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice."

III. Key Allegations and Witness Testimony

The trial has revealed extensive allegations against Combs, primarily centered around what prosecutors describe as a "criminal enterprise" he ran.

A. "Freak-Offs" and Coercion

A central theme of the prosecution's case revolves around "freak-offs," "King Nights," or "hotel nights"—terms used interchangeably to describe "drug-fueled sex marathons with male sex workers while Combs watched, directed, masturbated and sometimes filmed them."

• Cassie Ventura's Testimony: Combs' ex-girlfriend, Cassie Ventura, was a key witness for the prosecution. She settled a civil suit accusing Diddy of rape for $20 million. She testified about "years of Diddy's alleged abuse" and how he "coerced [her] into participating in 'freak-offs.'" Her mother, Regina Ventura, also testified, describing feeling "physically sick" when her daughter told her Combs had threatened to "release two explicit sex tapes." Texts from the court showed Cassie "feared being filmed, and consistently asked Combs whether there was footage she didn’t know about."

• "Jane's" Testimony: Another ex-girlfriend, testifying under the pseudonym "Jane," also alleged she was coerced into "sex sessions with male escorts."

• Sex Worker Testimonies: A male exotic dancer nicknamed "The Punisher" testified about "between eight and 12 sexual encounters with Combs and Cassie." He described them as "a fetish type thing" and, while he believed Cassie was consensual, he "did occasionally see her sigh or wince" and said she would frequently look at Combs "for cues." Another sex worker also reported being present when Combs was violent.

• Drugs and Logistics: Witnesses, including former personal assistant Brendan Paul, testified that Combs' employees procured drugs for these "freak-offs." Paul, who was arrested for cocaine possession at a Miami airport (which he later denied belonged to Combs), admitted to buying drugs for the rapper, stating that "cocaine was taken in 'rare, rare, uses,' according to the ex-assistant. Marijuana was also a regular for Paul." He described a culture of "loyalty" instilled by Combs and recalled Combs' fury when a bag containing drugs was misplaced.

B. Violence and Control

The indictment explicitly states that Combs "engaged in a persistent and pervasive pattern of abuse toward women and other individuals," which was "at times, verbal." It also mentions instances of physical violence, such as a time when Combs "kicked, dragged, and threw a vase at a woman as she was attempting to leave."

• Dawn Richard: A former member of Diddy-backed groups Danity Kane and Dirty Money, "told the court Combs was 'frequently' violent with Cassie and threatened her life if she spoke out about it."

• Kerry Morgan: Cassie's former best friend, said Combs was prone to "mood swings" and "once choked her - and described two occasions she allegedly saw him beat Cassie."

• Brendan Paul's Experience: Paul's testimony also hinted at the demanding nature of working for Combs, with another assistant advising him to "get in, get out, if you have a girlfriend, break up with her, and you’re never going to see your family." Paul himself sometimes "stayed awake for three straight days."

• Kid Cudi: Briefly dated Cassie and testified that Combs "broke into his home, 'messed with' his dog and opened some of his Christmas presents during a break-in."

C. Evidence from Raids

Federal agents raided two of Combs' properties in Los Angeles and Miami in March 2024. Photos from the raids revealed items prosecutors claim support their case:

• "Troves of baby oil, various drugs, firearms, and pieces of lingerie."

• "Hundreds of bottles of baby oil and lubricants scattered about Combs’ Los Angeles home," consistent with testimony that Combs "wanted a lot of baby oil to be used during 'freak offs.'"

• At his Miami home, agents seized "similar items including drugs, drug paraphernalia, and firearms."

IV. Defense Strategy

Combs' legal team maintains that all encounters were consensual and that his accusers "participated willingly in the so-called 'Freak-Offs.'"

• Consensual Activity: Combs' lawyers claim that nine videos possessed by prosecutors, if shown, would prove "adults having consensual sex, plain and simple" and contain no evidence of "violence, coercion, threats, sex trafficking or other claims made against Combs."

• Defense in Closing Arguments: Defense attorney Marc Agnifilo argued that prosecutors "twisted his drug use and swinger lifestyle into a sex trafficking and racketeering case that could put him behind bars for life." He stated, "He is none of these things. He is innocent." Agnifilo also "mocked the prosecution’s assertion that Combs and his underlings engaged in hundreds of racketeering acts, as well as the government’s suggestion that many of the sex marathons at the heart of the case were crimes," warning jurors, "Where’s the crime scene? It’s your sex life."

• No Defense Witnesses: Combs chose not to testify, and his defense lawyers "won't call any witnesses."

• Racism Claim: Combs' attorneys argued that the Mann Act, under which he was charged with transportation to engage in prostitution, has "racist origins," and that Combs "has been singled out because he is a powerful Black man, and he is being prosecuted for conduct that regularly goes unpunished."

V. Financial and Public Impact

Sean Combs was once estimated to be worth $740 million in 2019, with a diverse business empire including Bad Boy Records, fashion lines (Sean John), liquor brands (DeLeón tequila), and Revolt TV. Forbes now conservatively estimates his wealth at $400 million.

• Business Repercussions: Following the allegations and his arrest, many brands and institutions have distanced themselves from Combs. Macy's began removing his Sean John line, he left his role at Revolt Media, and numerous brand partnerships were cut. His family's reality TV show was pulled, and the Recording Academy evaluated his Grammy invitation. His music has seen a "plummet" in radio airplay and streaming activity, with some stations pulling his music entirely. Howard University revoked his honorary degree and terminated a $2 million gift.

• Documentaries: Multiple documentaries have been produced or are in development about the allegations, including TMZ's The Downfall of Diddy, Netflix's Diddy Do It (executive produced by 50 Cent), Peacock's Diddy: The Making of a Bad Boy, and Investigation Discovery's The Fall of Diddy.

• Public Support and Controversy: Some individuals have shown support for Combs, with "Free Puff" or "Free $Diddy" shirts being distributed, allegedly for $20 an hour. Kanye West publicly expressed support, calling Combs a "hero" and "idol" and urging Donald Trump to "free Combs." Donald Trump Jr. also linked celebrity endorsements for Kamala Harris to Diddy's "freak-off" parties, baselessly claiming it was a "blackmail scheme." Former President Donald Trump stated he would "look at the facts" if asked about a potential pardon for Combs.

VI. Civil Lawsuits

Separate from the criminal trial, Combs faces "dozens of civil claims" from alleged victims as young as 10 at the time of the alleged incidents, dating from 1990 to 2023. These include accusations of "rape, drug-facilitated sexual assault, child sexual abuse, and sexual harassment." While many lawsuits were filed after his criminal charges, some preceded them.

• Notable Civil Suits:Cassie Ventura: Filed a high-profile lawsuit in November 2023 alleging rape, trafficking, and physical assault over ten years, which was settled the next day for $20 million.

• Liza Gardner and Joi Dickerson-Neal: Filed lawsuits in November 2023 alleging sexual assault in 1990 and 1991, respectively. Dickerson-Neal also claimed Combs drugged and sexually assaulted her and shared the video.

• Jane Doe (Detroit): Alleged in December 2023 that she was gang-raped as a teenager by Combs, Bad Boy Records' president Harve Pierre, and a third assailant.

• Rodney Jones: A former producer, sued Combs in February 2024 for allegedly forcing him to engage in sex acts with sex workers and accusing him of sex trafficking. While his RICO claims were dismissed, his sex trafficking allegations could proceed.

• Dawn Richard: Filed a lawsuit in September 2024 alleging sex trafficking, sexual assault, and false imprisonment, and stated she was a witness to Cassie's claims.

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

• Jay-Z and Combs Lawsuit: In December 2024, a civil lawsuit accused both Combs and Jay-Z of raping a 13-year-old girl in 2000; this lawsuit was "voluntarily dropped with prejudice" in February 2025, meaning it cannot be brought again.

• By January 2025, Rolling Stone reported "over forty lawsuits against Combs."

VII. Outlook

The trial is drawing to a close, with jurors set to deliberate soon. The outcome will depend on whether the prosecution's extensive testimony and alleged evidence of a "criminal enterprise" can overcome the defense's arguments of consensual activity and the twisting of Combs' "swinger lifestyle" into criminal charges.