Diddy Trial Day 2: Cassie to Testify After Escort Cross-Exam Raises Doubts

Diddy Trial Day 2: Cassie to Testify After Escort Cross-Exam Raises Doubts.

As day two of Sean “Diddy” Combs’s sex trafficking trial began, the mood in the Manhattan federal courtroom was noticeably tenser. Reporters shuffled notes, observers murmured, and a distinct pause fell over the gallery as former escort Daniel Phillip returned to the stand — while the expected testimony from Cassie Ventura loomed in everyone’s minds.

Combs, 55, faces five felony charges, including sex trafficking by force, racketeering conspiracy, and the transportation of individuals to engage in prostitution. He’s pleaded not guilty to all counts and maintains his relationships were entirely consensual.

🛑 Recap: Day One Set the Tone — and the Stakes

Before diving into today’s testimony, let’s quickly revisit what happened on Day 1, which opened with heavy allegations and jarring evidence:

• Surveillance footage from 2016 was played for jurors, allegedly showing Combs attacking Cassie in a hotel hallway, wearing only a towel as he dragged and kicked her.

• Prosecutors painted Combs as a man who “trafficked women under the guise of luxury,” orchestrating group sex scenarios — called “freak-offs” — while secretly recording and blackmailing victims.

• Defense attorneys, however, called the claims exaggerated, insisting the trial was really about "jealousy, infidelity, and money."

• Two key witnesses testified: hotel guard Israel Florez, who said Combs tried to bribe him; and escort Daniel Phillip, who detailed being paid for sex with Cassie as Combs watched.

🔍 Day 2: Cross-Examination Chips Away at Testimony

Today began with defense lawyer Xavier Donaldson digging into Phillip’s testimony, zeroing in on inconsistencies.

“Did Cassie seem intoxicated the first time you met?”
“No,” Phillip answered.
“Was she in complete control?”
“I cannot say that,” Phillip replied.

Donaldson also grilled Phillip on a key contradiction: on Monday, he testified that after an alleged violent outburst, Combs said, “Are y’all ready to continue?” But in a 2023 interview, Phillip reportedly said Combs told him to leave the hotel.

This discrepancy may seem small — but in a sex trafficking trial, where coercion and consent are everything, it could carry weight.

👀 Cassie Set to Take the Stand — but Not Without Drama

Cassie, now eight months pregnant, is expected to testify after Phillip. That’s prompted objections from the defense, with attorney Marc Agnifilo urging the judge not to allow jurors to see her pregnancy:

“Pregnancy is beautiful and wonderful. It’s also a source of potential sympathy,” he argued.

Judge Arun Subramanian hasn’t yet ruled. But let’s be honest — regardless of where she sits, her presence will be powerful. In 2023, Cassie’s civil suit set off this criminal investigation. And if her testimony mirrors what was alleged in court filings — forced sex, beatings, threats of leaked tapes — the stakes for Combs could escalate rapidly.

⚖️ “Freak-Offs,” Violence, and Power Games

The most disturbing claims so far involve voyeuristic encounters arranged by Combs, during which he allegedly filmed Cassie having sex with male escorts, sometimes under duress. According to prosecutors, this wasn’t kink — it was control.

Phillip testified that Combs took photos of his driver’s license and that he felt “threatened”. At one point, after a violent episode, Cassie reportedly jumped into Phillip’s lap, "shaking from head to toe."

The jury also heard that Combs would instruct the escort and Cassie on how to perform, sometimes using a camcorder.

Editor's note: An earlier version of this article stated Combs used a smartphone camera during these events. It was later clarified that both smartphones and camcorders were allegedly used.

📌 Who’s Who

• Sean Combs: Grammy-winning mogul turned defendant.

• Cassie Ventura: Singer, model, and former partner — the prosecution’s key witness.

• Daniel Phillip: Escort paid for sex with Cassie while Combs watched.

• Emily Johnson: Lead prosecutor.

• Xavier Donaldson / Teny Geragos: Combs’s defense attorneys.

• Judge Arun Subramanian: Presiding over the trial in Manhattan federal court.

  

🎯 What’s Coming Next?

If today's courtroom energy was any sign, Cassie’s testimony will shift the entire dynamic. Prosecutors are expected to walk her through the decade-long relationship, the alleged abuse, and the web of emotional, sexual, and financial control she says Combs exerted.

Will her story hold up under cross-examination? Can the defense frame it as revenge from a bitter ex? That remains to be seen.

But if jurors believe even a fraction of what’s been alleged — especially with the video evidence and witnesses backing it — this trial could end with the dismantling of one of hip-hop’s most iconic legacies.

Stay tuned. We’ll be back tomorrow with a full recap of Day 3.