Cassie forced to read aloud explicit messages with Sean 'Diddy' Combs at
his sex trafficking trial
[May 16, 2025]
By MICHAEL R. SISAK and LARRY NEUMEISTER
NEW YORK (AP) — R&B singer Cassie was pressed to read aloud her own
explicit messages to ex-boyfriend Sean “Diddy” Combs in federal court
Thursday, including texts that showed her expressing desire for the
drug-fueled group sex she previously testified left her traumatized.
Lawyers for Combs sought to portray Cassie to the jury as a willing and
eager participant in the music mogul's sexual lifestyle. Combs has
pleaded not guilty to federal sex trafficking and racketeering charges.
His defense says that, while he could be violent, nothing he did
amounted to a criminal enterprise.
Prosecutors say he exploited his status as a powerful music executive to
violently force Cassie and other women into these marathon encounters
with sex workers, called “freak-offs,” which sometimes lasted days.
Combs insists all the sex was consensual. He's also accused of using his
entourage and employees to facilitate illegal activities, including
prostitution-related transportation and coercion, which is a key element
of the federal charges.
Messages between Combs and Cassie — both romantic and lurid — were the
focus of the fourth day of testimony in a Manhattan courtroom. Defense
attorney Anna Estevao read what Combs wrote, while Cassie recited her
own messages about what she wanted to do during the freak-offs. Cassie’s
testimony will resume Friday.
Combs, 55, has been jailed since September. He faces at least 15 years
in prison if convicted.
Defense highlights Cassie's messages to Combs
While Cassie, whose legal name is Casandra Ventura, has said she felt
compelled to participate in freak-offs to keep Combs happy, Estevao
pointed to message exchanges where Cassie appeared excited about the
sexual encounters and raised the idea of having one on her own.
In August 2009, Combs asked when she wanted the next encounter to be,
and she replied “I’m always ready to freak off.” Two days later, Cassie
sent an explicit message and he replied in eager anticipation. She
responded: “Me Too, I just want it to be uncontrollable.”
Later that year, however, she also sent Combs messages that she was
frustrated with the state of their relationship and needed something
more from him than sex.
Estevao also noted a July 2013 text message exchange where Cassie wrote
to Combs, “Wish we could've FO'd before you left,” using the initials of
freak-off.
In a 2017 text message, Cassie told Combs: “I love our FOs when we both
want it." On the stand Thursday, Cassie explained: “I would say loving
FOs were just words at that point.”
Cassie complained at one point that jurors weren’t hearing the full
context of the messages the defense was highlighting, saying, “There’s a
lot we skipped over.”
Combs’ attorney presented Cassie with sexual texts she sent before a
2016 encounter at a Los Angeles hotel, where Combs was caught on
surveillance video kicking and dragging her in a hallway. Cassie said
she wanted to get the encounter over with, in order to keep Combs happy
and avoid a scene ahead of movie premier she was attending days later.
Estevao raised instances of Cassie's anger with Combs and her admitted
jealousy over attention he gave other women. Cassie said Combs didn't
want her seeing anyone else, but the same rules didn't apply to him.
Cassie testified that after a few years with Combs she longed to be a
bigger part of his life but he wouldn’t let her in. Their relationship
lasted from 2007 to 2018.
A packed courtroom watches Cassie's testimony
The cross-examination didn’t have the combative tone of a stereotypical
defense grilling. Estevao spoke gently, and she and Cassie seemed like
two friends chatting at times.
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Cassie Ventura, left, and Sean "Diddy" Combs appear at The
Metropolitan Museum of Art's Costume Institute benefit gala
celebrating "China: Through the Looking Glass" in New York on May 4,
2015. (Photo by Charles Sykes/Invision/AP, File)
 The 38-year-old Cassie — who is in
the third trimester of pregnancy with her third child — has held up
well on the witness stand. She cried several times during the
previous two days of questions by the prosecution, but for the most
part has remained composed and matter-of-fact as she spoke about the
most sensitive subjects.
The Associated Press does not typically name people who say they
have been sexually abused unless they come forward publicly, as
Cassie has.
As the explicit messages were read, Combs appeared relaxed at the
defense table, sitting back with his hands folded and legs crossed.
The courtroom was packed with family and friends of Combs,
journalists, and a row of spectator seats occupied by Cassie’s
supporters including her husband.
During a break, Combs stood at the table, huddling with his lawyers,
holding a pack of Post-It notes in one hand and a pen in the other.
At one point, he turned to the gallery and acknowledged a few
reporters who were studying his demeanor. “How you doing?” he asked.
Combs' daughters were not in the courtroom Thursday.
Jurors leaned forward in their seats to follow along as the messages
were displayed on monitors in front of them in the jury box. One
woman shook her head as a particularly explicit message was shown. A
man stared intently at the screen, pressing his thumb to his chin.
Other jurors appeared curious and quizzical, some looking at Cassie
or jotting notes.
Defense draws a comparison to the ‘swingers lifestyle,’ but
Cassie pushes back
While prosecutors have focused on Combs’ desire to see Cassie having
sex with other men, she testified that she sometimes watched Combs
have sex with other women. She said Combs described it as part of a
“swingers lifestyle.”
Estevao asked Cassie directly whether she thought freak-offs were
related to that lifestyle.
“In a sexual way,” Cassie responded, before adding: “They’re very
different.”
Cassie said Tuesday that Combs was obsessed with a form of voyeurism
where “he was controlling the whole situation.” The freak-offs took
place in private, often in dark hotel rooms, unlike Combs’ very
public parties that attracted A-list celebrities.
She testified she sometimes took IV fluids to recover from the
encounters, and eventually developed an opioid addiction because it
made her “feel numb” afterward.
Cassie’s testimony on cross-examination was in contrast to previous
days, when she described the violence and shame that accompanied her
“hundreds” of freak-offs during her relationship with Combs.
Cassie's lawsuit sparked the criminal case against Combs
Cassie testified Wednesday that Combs raped her when she broke up
with him in 2018, and had locked in a life of abuse by threatening
to release videos of her during the freak-offs.
She sued Combs in 2023, accusing him of years of physical and sexual
abuse. Within hours, the suit was settled for $20 million — a figure
Cassie disclosed for the first time Wednesday — but dozens of
similar legal claims followed from other women. It also touched off
a law enforcement investigation into Combs that has culminated in
this month's trial.
___
Associated Press journalists Julie Walker in New York and Dave
Collins in Hartford, Connecticut, contributed to this report.
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