On June 24, 2025, Day 29 of the high-profile trial against Sean “Diddy” Combs unfolded in a Manhattan federal courtroom, delivering a gripping mix of legal maneuvering, explicit evidence, and a pivotal shift as the defense began its case. The music mogul, charged with racketeering conspiracy, sex trafficking, and transportation for prostitution, sat attentively as his legal team, led by Teny Geragos, challenged the prosecution’s narrative with a barrage of text messages, financial records, and private videos.
With the trial barreling toward closing arguments, the jury’s impending deliberations loomed large, raising the question: will they reach a verdict before the July 4th holiday?
A Tense Morning: Cross-Examining the Prosecution’s Final Witness
The day kicked off with Geragos resuming her cross-examination of Homeland Security Investigations Special Agent Joseph Cerciello, the prosecution’s final witness. Geragos zeroed in on text message exchanges between Combs and a woman referred to as “Jane” in court, whose identity is protected due to the sensitive nature of the case. These messages, spanning 2021 to 2023, painted a picture of a consensual relationship, according to the defense. In one December 2021 text, Jane invited an escort named Cabral Williams to join her and Combs, writing,
“LMK if you wanna come tonight.”
Geragos pressed Cerciello on whether this showed Jane’s initiative, countering claims that Combs coerced women into so-called “freak-offs”—drug-fueled sex parties at the heart of the prosecution’s allegations.
Geragos didn’t stop there. She introduced explicit videos, shown exclusively to the jury due to privacy restrictions, to bolster the defense’s argument that Jane’s interactions with Combs were voluntary. One video from June 2024 featured audio of a bass playing and Jane’s voice, though technical glitches—like a juror’s device flashing “Low Battery”—briefly disrupted the presentation. Geragos also grilled Cerciello on metadata to confirm the videos’ authenticity, ensuring the jury understood their context. Another message from Jane read,
“I love you, can’t wait to see you,”
With heart emojis, which Geragos used to portray a romantic, not coercive, dynamic.
Financial Records: Personal or Criminal Enterprise?
The defense pivoted to financial records to separate Combs’ personal spending from the prosecution’s claim that he ran a criminal enterprise through his businesses, like Bad Boy Entertainment. Geragos highlighted a $74,000 transfer from Combs’ personal bank account, covering expenses like $324.50 and $760.25 for Jane’s transportation and Cabral’s travel from Atlanta to Florida. A $22,000 account transfer was also scrutinized, with Geragos arguing these were personal transactions, not evidence of a trafficking ring. The prosecution countered, with Assistant U.S. Attorney Emily Johnson asserting that Combs’ payments for cross-state travel supported their sex trafficking charge. A brief sidebar followed, as tensions flared over the scope of these financial exhibits.
Legal Maneuvers: Rule 29 Motion and Trial Timeline
After Cerciello’s testimony wrapped, Geragos quipped,
“Thank you, Agent, go back to keeping New York City safe”
The jury was dismissed for a Rule 29 motion. This standard defense request asks the judge to dismiss the case for insufficient evidence. Still, legal observers noted that Judge Arun Subramanian is unlikely to grant it, given the volume of prosecution evidence. The motion marked a transition, as the defense prepared to present its case, which they signaled would be concise, relying on exhibits rather than a parade of witnesses.
The trial’s timeline is tight. Wednesday, June 25, will see a charge conference to finalize jury instructions and the verdict form. Closing arguments are set for Thursday, with each side allotted four hours to make their case. The jury will then have until July 3 to deliberate before the court breaks for the holiday. The compressed schedule has sparked speculation about whether the jury can resolve the complex charges—carrying a potential life sentence for Combs—in just six days.
The Defense’s Strategy: Consent vs. Coercion
Throughout the day, Geragos hammered on consent, using Jane’s texts to undermine the prosecution’s portrayal of Combs as a manipulative orchestrator. In one 2023 message, Jane wrote,
“Daddy wanna see Mommy be bad tonight,”
followed by explicit emojis and promises to “blow your mind.” Geragos asked Cerciello if this suggested enthusiasm, not victimhood. Another text showed Jane joking about a “freak store” run, while Combs responded playfully,
“Hurry up, she is at hotel and she is horny as hell.”
The defense argued these exchanges reflected mutual desire, not a criminal scheme.
The prosecution, however, stood firm. Johnson objected to some texts as hearsay, like one where Jane demanded money, which Geragos claimed showed financial motive rather than trafficking. Judge Subramanian sustained several objections, limiting the defense’s ability to introduce certain messages, such as a 2017 text deemed too old to be relevant. Johnson also highlighted a text where Combs asked Jane if she could
“freak off without taking drugs,”
With Jane replying,
“Yes,”
arguing it was inadmissible hearsay. The judge overruled this objection, allowing the jury to hear it.
Cassie Ventura’s Shadow Looms
Though not testifying, Cassie Ventura, Combs’ former girlfriend, remained a focal point. Geragos referenced texts where Ventura allegedly bought baby oil
“because she just couldn’t stop herself,”
, suggesting her willing participation in intimate encounters. The prosecution countered that Ventura’s actions were with her boyfriend, not evidence of a broader trafficking scheme. A text where Ventura called herself Combs’ “little freak” was admitted. Still, others, like one requesting an explicit photo, were debated fiercely, with the judge overruling some objections and sustaining others.
Courtroom Dynamics and Technical Hiccups
The courtroom wasn’t without its quirks. Combs passed a note to attorney Nicole Westmoreland, who whispered to co-counsel Marc Agnifilo, hinting at real-time strategy adjustments. Geragos requested a restroom break before the jury entered, and later noted that the jurors’ high-tech devices had turned off during lengthy arguments. One video presentation was delayed when three jurors’ devices malfunctioned, prompting the court to swap in charged replacements. The public screen remained off for much of the day, leaving spectators in the dark about some exhibits—a frustration for those following the case closely.
What’s Next?
As Day 29 concluded, the defense’s case was poised to continue, though its brevity suggests they’re banking on the seeds of doubt planted during cross-examinations. The prosecution’s narrative of Combs as a predatory mogul clashes with the defense’s portrayal of consensual, if unconventional, relationships. The jury’s interpretation of the evidence—texts, videos, and bank records—will decide Combs’ fate.