Inside Sean ‘Diddy’ Combs’ all-star defense team

By Kara Scannell, CNN

New York (CNN) — Nine attorneys – five men and four women – fill two tables in the courtroom for Sean ‘Diddy’ Combs.

Some are confrontational cross examiners, others take a softer approach to witnesses and a handful are focused solely on making legal arguments to try to get certain exhibits in and others out.

But they all answer to one person: Combs himself.

Attorney Brian Steel was about to finish his cross examination of rapper Kid Cudi last month when he paused and walked over to Combs at the defense table. The two men conferred in a whisper before Steel said he had no further questions.

As another lawyer questioned Combs’ former girlfriend Cassie Ventura, whose allegations are at the center of the criminal case, Combs scribbled on Post-It notes and passed one after another to his lead attorney Marc Agnifilo.

The stakes are high.

Combs has pleaded not guilty to five counts, including one count of racketeering conspiracy, two counts of sex trafficking and two counts of transportation to engage in prostitution. If convicted of the most serious charges, Combs could face as much as life in prison and a minimum sentence of 15 years.

During six weeks of testimony, the jury reviewed dozens of text messages and financial records and saw photos of injuries sustained by Ventura that were allegedly caused by Combs. Jurors also viewed graphic materials, which included sexually explicit videos during direct and cross examination of a witness.

Prosecutors have called nearly three dozen witnesses. Two accusers testified that Combs forced them into having sex with male escorts. At least six people who worked for Combs testified about working long hours, getting drugs for Combs, being reimbursed for Combs’ personal expenses and setting up and cleaning up hotel rooms where authorities allege sex trafficking took place.

A security officer for the InterContinental Hotel in Los Angeles, where Combs was seen physically assaulting Ventura on a 2016 surveillance video first published by CNN, testified that Combs paid him $100,000 to obtain what he thought was the only copy of the footage.

Prosecutors alleged Combs, aided by security guards, personal assistants and others at Bad Boy Entertainment, was involved in a racketeering conspiracy that involved forced labor, kidnapping, arson, sex trafficking, bribery, obstruction of justice and drug offenses.

Combs’ defense will take center stage in the trial this week and have a chance to call their own witnesses.

But like most defense teams, they have been trying their case since the start, attempting to cast doubt on the prosecution’s case by challenging the credibility of the government’s witnesses.

“You can’t wait until your case to propagate your theory, you have to do it in their case, so every witness furthers your narrative” said Joey Jackson, a criminal defense lawyer and CNN legal analyst. “It’s very difficult to defend against all of this horrific behavior,” Jackson added.

To reach a guilty verdict, the jury of eight men and four women must find Combs reached an agreement with someone and at least two of those so-called predicate acts were committed within 10 years. The jury must be unanimous on the acts. Combs is also accused of sex trafficking Ventura and a former girlfriend who testified under the pseudonym “Jane” by force, fraud or coercion.

Combs’ lawyers have pushed the opposite theory – that while he did physically assault Ventura and was a bad boyfriend, the sex acts were part of a consensual kinky lifestyle called “Freak Offs,” “king nights” or “hotel nights.” They sought to show the jury that Bad Boy was a legitimate business and Combs’ wild side was part of his personal, not professional, life.

“Every single witness has to have a clear objective. I don’t think it’s about meandering or grandstanding, you have to get in and out,” Jackson said.

The Legal Team

Marc Agnifilo and Teny Geragos, who have known Combs for years, are leading his packed defense team.

Agnifilo started as a local and federal prosecutor but has spent most of his career in criminal defense.

He is currently representing Luigi Mangione, the accused killer of United Healthcare CEO Brian Thompson, with his wife Karen Friedman Agnifilo.

For nearly two decades, he worked closely with criminal defense attorney Ben Brafman, who previously defended Combs in a case related to a shooting at a nightclub, and together they represented Dominique Strauss-Kahn, the former head of the International Monetary Fund who faced sexual assault charges but were later dropped.

Agnifilo has handled the cross-examinations of some former Bad Boy employees and law enforcement officials and is taking the lead when addressing the judge.

Geragos, the daughter of celebrity attorney Mark Geragos, left Brafman’s firm to join Agnifilo, when he opened his own firm last year. They are an experienced trial duo, teaming up in past years to represent Nxivm founder Keith Raniere and former Goldman Sachs banker Roger Ng.

At the Combs trial, Geragos delivered the defense’s opening statement and handled the days long cross-examination of “Jane.”

Appellate specialists Alexandra Shapiro and Jason Driscoll are handling legal arguments over evidence, and Anna Estevao, who crossed examined Ventura, who until May worked at a law firm that is defending dozens of civil lawsuits against Combs that were filed in the wake of Ventura’s 2023 lawsuit. Combs has denied any wrongdoing.

On the eve of trial, Combs brought in three more attorneys to his team – Xavier Donaldson, a criminal defense lawyer in New York, and two trial attorneys from Atlanta, Steel and Nicole Westmoreland, who recently represented rapper Young Thug and a co-defendant in a criminal racketeering trial.

As the trial was underway, yet another lawyer appeared: Jonathan Bach, a colleague of Shapiro, to exclusively handle the cross examination of a government expert witness, psychologist Dawn Hughes. He’s since been absent from the courtroom.

Cross examination: BFF and the ‘Perry Mason’ moment

Each lawyer on the team has their own style. Some are more aggressive in their cross examination, while others tapped into what some legal analysts call the “best friend” approach.

As Estevao cross-examined Ventura, who was more than eight months pregnant at the time of her testimony, the attorney asked about Ventura’s accomplishments at age 21 when her relationship with Combs was starting.

“Fair to say that you were a celebrity in your own right?” Estevao asked, before adding, “And you’re very beautiful and charming?”

Those type of questions can be disarming and lower the guard of witnesses, making them more agreeable, attorneys say.

Ventura testified it was “always in the back of my mind” that Combs could physically hurt her if she didn’t participate in certain sex acts or try to blackmail her by threatening to release videos of the “Freak Offs.” When Estevao asked Ventura if part of the reason she participated in “Freak Offs” was to make Combs happy, she agreed.

“The school of thought can be a female can go a bit harder because in a sense optically, it’s not a man crossing that line of what may be victim shaming,” said Misty Marris, a criminal defense attorney.

Of the Ventura cross examination, she said, “It’s more gentle, more conversational and inviting somebody to be open.”

“Sometimes that’s very effective because the guard is let down from the witness,” she said.

The lead attorneys have used a similar approach. Agnifilo sounds almost apologetic when introducing himself to the witness he’s about to cross-examine, advising them if they don’t understand his question, they should tell him. And Geragos, who has a mastery of the lengthy exhibits, speaks in a casual, approachable manner, sometimes poking fun at herself.

Westmoreland is more direct when casting doubt on witness testimony. She challenged Bryana Bongolan, a friend of Ventura who testified that Combs dangled her over a 17-story balcony and threw her onto furniture, causing her injuries.

Prosecutors showed the jury a photograph of a large bruise on Bongolan’s leg that she testified was taken “the same day” as the injury and showed the jury the image’s metadata for the photo, indicating it was taken on September 26, 2016.

On cross examination, Westmoreland used a government exhibit of Combs’ hotel invoice from the Trump International Hotel and Tower in New York that showed him staying at the hotel from September 24 through September 29, 2016.

“You agree that one person can’t be in two places at the same time?” Westmoreland asked.

“In, like, theory, yeah,” Bongolan testified.

Outside the presence of the jury, Judge Arun Subramanian called the cross a “real Perry Mason moment” that, he said, “blew a hole through the direct testimony of Ms. Bongolan.”

Lawyers caution that long cross examinations can backfire and bore the jury. For several witnesses, Comb’s team’s cross examination went as long or longer than the prosecution’s questions.

One tactic that Comb’s lawyers have used repeatedly in questioning government witnesses is to repeat evidence that bolsters their defense.

Geragos, in opening statements, said the case is about “voluntary, adult choices made by capable adults and consensual relationships.”

To further her argument, Geragos asked a law enforcement officer called by prosecutors to re-read some of Ventura’s messages to Combs.

In one of those messages, Ventura wrote, “I’m always ready to freak off LOLOL.”

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CNN’s Lauren del Valle, Nicki Brown and Elizabeth Wagmeister contributed to this report.