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, on Tuesday they will call a former Syracuse basketball player who worked as Mr. Combs’s assistant and is alleged to have been his drug “mule.”

“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.” 

Federal prosecutors on Monday called two summary witnesses who both work in the Manhattan U.S. 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 “Freak Offs.” 

Mr. Combs’s now infamous 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’s family — including his children, some of them very young — and the public and the press are seated.

As the jurors 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’s longtime girlfriend, Ms. Ventura, whom he dated off and on between 2007 and 2018. She is a key witness who testified earlier in the trial. During cross-examination defense attorneys asked Ms. Ventura about these videotapes, and she confirmed that she had handed them over to prosecutors and that they were taken from her computer device. 

It appears that when agents raided Mr. Combs’s 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 more than 1,000 bottles of baby oil. 

Both Ms. Ventura and another alleged victim, who testified under the pseudonym Jane and who dated Mr. Combs between 2021 and 2024, told the court that the defendant would threaten to release videotapes 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 using blackmail, violence, and payments for rent, cars, 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. 

Attempting to prove the transportation for the purpose of prostitution charge, prosecutors also presented several flight itineraries, such as one flight Mr. Combs allegedly bought for a male escort named Jules Theodore to New York on December 11, 2009, returning to California on December 13, 2009. The escort was 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 to New York from Los Angeles 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 that was used to pay off the credit card was at Signature Bank, which belonged to “207 Anderson LLC, care of Bad Boy Entertainment Worldwide,” Special Agent Penland testified.  

Bad Boy Entertainment Worldwide is the music, media, and entertainment company founded by Mr. Combs that includes his Bad Boy record label that 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. 

The Racketeer Influenced and Corrupt Organization 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 conspired to participate in a criminal enterprise to commit a pattern of illegal activities over the course of at least 10 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. 

Mr. Combs’s 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. (Yet 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 wealthy 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 views 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.

But the RICO charge requires proof of a “criminal enterprise,” and Mr. Combs’s chief of staff, Kristrina Khorram, who has been mentioned repeatedly by almost every 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’s chief of staff was well aware of the freak offs, and 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.

In November 2022, Ms. Khorram texted Mr. Combs to ask 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 he 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’s 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 more than 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’s 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.