Jurors in the sex trafficking trial of the rapper Sean “Diddy” Combs were shown sexually explicit video footage of his notorious “Freak Off” parties in court on Monday. As federal prosecutors near the end of their case, they will call a former Syracuse Basketball player, who worked as Mr. Combs’ assistant, and is alleged to have been his drug “mule,” on Tuesday.  

“You horny,” Mr. Combs texted his then-girlfriend Cassandra Ventura in early January, 2013. 

“Lol, yeah,” Ms. Ventura replied.

“Would you like to celebrate Christmas and have a Freak Off tonight or Friday?” Mr. Combs then asked, adding “I have your Christmas present and stuff.” 

Sean ‘Diddy’ Combs, right, blows kisses to people in the audience during his sex trafficking and racketeering trial in Manhattan federal court, Monday, May 19, 2025, in New York. Elizabeth Williams via AP

Federal prosecutors called two summary witnesses on Monday, who both work in the Manhattan US Attorney’s Office, Special Agent DeLeassa Penland and a paralegal in the prosecutor’s office, Ananya Sankar, to enter into evidence and present to the jury text messages, travel records, credit card bills, hotel receipts and also video footage of the so-called “Freak Offs.” 

Mr. Combs’ now infamous freak off parties are alleged to have been drug-fueled sex orgies, to which the music producer invited male prostitutes to have sex with the women he was dating while he watched and pleasured himself. These parties, which have also been referred to as hotel nights, or king nights, depending on the witness, are said to have lasted up to 30 hours, sometimes even several days.

On Monday, the jury saw video footage of these freak offs for the first time during the trial, which began with jury selection on May 5 and is now on day 24 of witness testimony. The jurors were given headphones to watch the intimate video clips. Due to the sensitive content, the screens in the courtroom and screens at the attorney tables were mostly shut off, because they are visible to the gallery, where members of Mr. Combs’ family – including his children, some of them very young – the public and the press are seated. As the jurors’ gaze was focused on their individual screens, music and faint moaning sounds were slightly audible in the courtroom, coming through the headphones. Several jurors winced. One woman put her hand over her head as she watched. 

The video clips, lasting about 30 seconds each, dated from 2012 to 2014 and involved Mr. Combs’ long time girlfriend Ms. Ventura, whom he dated off-and-on from 2007 to 2018, and is a key witness and who testified earlier in the trial. During cross-examination defense attorneys asked Ms. Ventura about these video tapes, and she confirmed that she had handed them over to prosecutors and that they were taken from her computer device. 

Christian ‘King’ Combs, left, son of Sean “Diddy” Combs, arrives at Federal court for his father’s trial, Friday, June 13, 2025, in New York. AP Photo/Richard Drew

It appears that when agents raided Mr. Combs’ estates in Miami and in Los Angeles in March 2024, they did not find the tapes that he allegedly recorded of the freak offs. Instead Homeland Security agents found parts from two AR-15-style guns with their serial numbers removed, as well as magazines with ammunition. They also seized – from a large closet in one of the home’s primary bedrooms –  sex toys, condoms and boxes of stilettos, and over 1,000 bottles of baby oil. 

Both Ms. Ventura and another victim, who testified under the pseudonym “Jane,” and who dated Mr. Combs from 2021 to 2024, told the court that the defendant would threaten to release video tapes of them having sex with male escorts if they refused to fulfill his carnal desires and partake in more freak offs. He also allegedly threatened Ms. Ventura that he would publicize the tapes (and show them to her parents) if she dared to speak out about the physical abuse she claimed (and other witnesses confirmed) she endured for more than a decade. However, other than the tapes of the sexcapades that Ms. Ventura turned over, which were in her possession, federal agents could not find tapes solely belonging to Mr. Combs. 

Prosecutors allege that Mr. Combs coerced the women into having sex with other men, while taking drugs like ecstasy, ketamine or cocaine, by blackmail, violence, and paying their rents, their cars, their beauty treatments and more, and by essentially keeping them financially dependent on him.        

The freak offs are at the heart of the case against Mr. Combs, who is charged with racketeering conspiracy, sex trafficking and transportation for the purpose of prostitution. He faces a maximum sentence of life in prison, if convicted and has pleaded not guilty to all charges. 

Defense attorney Brian Steel, center, cross-examines Kid Cudi as Sean ‘Diddy’ Combs, far left, looks on during Combs’s sex-trafficking and racketeering trial in Manhattan federal court, May 22, 2025. Elizabeth Williams via AP

Attempting to prove the transportation for the purpose of prostitution charge, prosecutors also presented several flight itineraries, for example one flight Mr. Combs allegedly bought for a male escort named Jules Theodore from Los Angeles to New York on December 11, 2009, returning to California on December 13, 2009, to meet him and Ms. Ventura at the London Hotel in Manhattan.  

In a text message sent to his personal finance director, Toni Bias, the defendant asked Mr. Bias, “Hey, I need a FLT (flight) booked for Friday 4:00 p.m. or 3:00 p.m. from LA to NYC, reg (regular) room at London Hotel under Jules Theodore, ASAP. Let me know when it’s done PLS.”  

Jurors were then shown flight records for Ms. Ventura, who flew from Los Angeles to New York on December 7, 2009 and returned on December 16. 

The flights were paid with an American Express card that, as the jury learned, belonged to Mr. Combs. The bank account which was used to pay off the credit card, was an account at Signature Bank, which belonged to “207 Anderson LLC, care of Bad Boy Entertainment Worldwide,” Special Agent Penland testified.  

Cassie Ventura and Sean ‘Diddy’ Combs appear at the Metropolitan Museum of Art’s Costume Institute benefit gala celebrating ‘China: Through the Looking Glass’ on May 4, 2015. Charles Sykes/Invision/AP, file

Bad Boy Entertainment Worldwide is the music, media, and entertainment  company, founded by Mr. Combs which includes his record label Bad Boy records, which launched the careers of legendary hip hop artists such as Notorious B.I.G, Faith Evans and Mary J Blidge in the 1990s.  

The company was also listed on Ms. Ventura’s travel invoice, as the documents showed. 

By proving that Mr. Combs used his business account to pay for flights for male prostitutes and (for his ex-girlfriend to travel to have sex with these prostitutes) across state lines, prosecutors also intend to establish that Mr. Combs led a “criminal enterprise,” which is a key factor in the racketeering conspiracy charge. 

Racketeering conspiracy, also known as Racketeer Influenced and Corrupt Organization Act, or the RICO act, was passed by Congress in 1970, signed into law by President Nixon and used to prosecute the Mafia and organized crime. The charge alleges that a group of individuals, meaning more than one person, conspired to participate in a criminal enterprise to commit a pattern of illegal activities over the course of at least ten years. Unlike general conspiracy charges, which focus on a single criminal act, racketeering conspiracy involves a series of crimes committed over time as part of a broader operation, such as assault, bribery, kidnapping, arson, and prostitution. 

Sean ‘Diddy’ Combs and Cassie attend the ‘Heavenly Bodies: Fashion & The Catholic Imagination’ Costume Institute Gala at the Metropolitan Museum of Art on May 7, 2018. Neilson Barnard/Getty Images

Mr. Combs’ attorneys scoff at the idea that his freak off parties were organized crime, or sex trafficking. They say federal prosecutors are criminalizing consensual sexual behavior among adults, and that while Mr. Combs may be guilty of domestic abuse, that’s not what he’s charged with. (Though the assault is one of the alleged criminal acts in the RICO charge.) 

But racketeering laws were designed to facilitate convictions of powerful crime bosses who always stayed one step removed from the commission of crimes, and it’s very hard for a defendant – even one as rich as Mr. Combs – to beat a federal racketeering prosecution.

As prosecutors wrap up their case, they plan to finish witness testimony by Wednesday afternoon, the racketeering conspiracy charge seems to be the weakest link in the five count indictment. Proving the two sex trafficking counts, which list Ms. Ventura and Jane as the victims, will largely depend on how credible the jury will view the women’s testimonies, while Ms. Ventura’s accusations appear to carry more weight because several other witnesses confirmed them. 

Prosecutors will also need to convince jurors that traveling with girlfriends across state lines constitutes a violation of sex trafficking laws designed to stop organized prostitution rings.

Former bodyguard Gene Deal arrives for the the Sean ‘Diddy’ Combs sex-trafficking trial at Manhattan federal court on May 27, 2025. Adam Gray/Getty Images

But the RICO charge requires proof of a “criminal enterprise,” and Mr. Combs’ chief of staff, Kristrina Khorram, who has been mentioned over and over again by almost every single witness, will not testify at the trial. 

Instead prosecutors presented yet more text messages involving Ms. Khorram on Monday. The jury saw messages sent between Ms. Khorram and Mr. Combs, and Ms. Khorram and Ms. Ventura, and Ms. Khorram and Jane. These messages proved that Mr. Combs’ chief of staff was well aware of the freak offs, that she would help set up and book the hotel rooms, organize drug deliveries and discuss the cash deliveries presumably intended to pay the male escorts.

In one message, Ms. Khorram texted Ms. Ventura, “Hi, Dave is at your door with the green.” Dave Shirley was a former personal assistant of Mr. Combs. 

Another message from Ms. Khorram to Mr. Combs read, “Hotel called, Paul coming up.” Jane had previously testified that she and Mr. Combs would often have hotel nights with a man called Paul.

Witness Daniel Philip walks into the courtroom in Manhattan federal court, Tuesday, May 13, 2025, in New York. Elizabeth Williams via AP

In November, 2022, Ms. Khorram texted Mr. Combs, asking if his head of security needed to bring anything with him on a flight to meet Mr. Combs in Miami. “15 pills of molly,” Mr. Combs replied in his message. And then texted Ms. Khorran not to text about it anymore. 

On Tuesday, prosecutors want to call Brendan Paul, a former Syracuse University basketball player, who worked as Mr. Combs’ assistant and was accused of being his drug “mule” by the music producer Rodney “Lil Rod” Jones, who filed a civil lawsuit against Mr. Combs, alleging that the defendant “sexually harassed, drugged and threatened him” for over a year. In his lawsuit Mr. Jones claimed that Mr. Paul “acquired” and “distributed” “drugs and guns” for the rapper.

Mr. Paul was arrested, shortly after Mr. Combs’ houses were raided in the spring of 2024 and charged with felony cocaine possession. He entered a plea deal with federal prosecutors. 

His testimony is expected to last the entire day on Tuesday.