Lawyer for Sean ‘Diddy’ Combs grills star witness Cassie Ventura over ‘freak offs’

Defence shows messages to argue singer willingly participated in sex parties.

Cassie Ventura testified during Sean ‘Diddy’ Combs’s sex-trafficking trial in New York City. Photo: Jane Rosenberg/Reuters

A lawyer for Sean “Diddy” Combs on Thursday argued that singer Cassie Ventura was so deeply in love with the music mogul that she willingly participated in days-long, drug-fuelled sex parties.

During the cross examination of Ventura, who is prosecutors’ star witness, Combs lawyer Anna Estevao and the singer read for the jury a series of BlackBerry messages exchanged by the couple. In one 2009 message, Combs asks Ventura when she wanted to have a “freak off,” or sex session during which Combs would watch her have sex with a male escort.

“I’m always ready to freak off, LOLOL,” said Ventura, 38 years old, reading her reply from the witness stand.

The pair then discussed scheduling the freak off, with Ventura saying that a Friday night would be best so they could recover for the workweek. Combs’s lawyer then displayed an explicit message Ventura wrote to Combs.

Cassie Ventura and Sean "Diddy" Combs in 2017. Picture: Chris Pizzello/Invision/AP

“I can’t wait to watch you,” said Estevao, reading a message from Combs. “I want you to get real hot.”

Ventura, who is eight-and-a-half months pregnant, then asked the judge for a break.

Thursday was the third day on the stand for Ventura. Prosecutors have accused Combs of running a criminal enterprise for two decades with the help of his bodyguards and other high-ranking employees. They said that he physically abused and sexually exploited Ventura for years, and forced her to have sex with male escorts during elaborately choreographed group sex sessions. Under questioning by a prosecutor earlier this week, Ventura told jurors that Combs used threats and violence to control her.

Lawyers for Combs have acknowledged his “swinger” lifestyle and violent behaviour, but said his alleged victims were adults who chose to take part in the sexual activity. Combs, 55, has pleaded not guilty to sex trafficking and other offences.

Thursday’s cross-examination is key to the defence’s argument that the sexual activity was consensual, not coerced. Defence attorneys are also expected to highlight a $20-million settlement of a lawsuit Ventura filed against Combs in 2023.

Earlier Thursday, defence lawyer Estevao showed jurors a series of messages Combs and Ventura exchanged in the early years of their relationship. Ventura told the jury that Combs was sweet and attentive, and she wanted to make her boyfriend happy.

“You and Sean Combs were in love for 11 years, right?” Estevao asked Ventura.

“Yeah,” replied Ventura softly.

Some of the messages showed she craved more time with Combs, whom she calls “Pop pop.”

“I haven’t talked to you at all,” she wrote in 2010. “I know you can take three minutes out of your day to talk to me and you don’t even try.”