Sean ‘Diddy’ Combs Jury to Decide if He Led an Entourage or a Criminal Enterprise

Running the life of Sean Combs has long involved a large retinue of employees, including security guards, personal assistants, household staff and higher-ranking supervisors.

At the music mogul’s trial on charges of racketeering conspiracy and sex trafficking, the jury will be confronted with the question of whether Mr. Combs led a typical celebrity entourage or, as prosecutors will argue, a criminal enterprise responsible for enabling years of sexual exploitation and other crimes.

The selection of that jury begins on Monday as prosecutors and defense lawyers work to choose a 12-member panel for a sprawling case that will put much of Mr. Combs’s life on trial and focus particular scrutiny on the conduct of his employees over two decades.

The government says employees set up hotel rooms, procured drugs and arranged for male prostitutes ahead of what prosecutors have described as “drug-fueled coercive sex marathons.” They paid women to keep them under Mr. Combs’s financial control, investigators say, and when Mr. Combs became violent, they managed the aftermath.

“They facilitated the cover up of those assaults,” prosecutors wrote of Mr. Combs’s staffers in court papers, “by helping the defendant bribe witnesses, arranging treatment for the victims, secreting the victims away from the public until their injuries healed, and contacting victims in the aftermath of the defendant’s assaults.”

In court papers, prosecutors have outlined a pattern of crimes dating back to 2004 that include arson, kidnapping, forced labor, bribery, obstruction of justice and drug violations. Over what is expected to be about two months of testimony, the prosecution will seek to show that members of Mr. Combs’s staff helped enable these crimes, as well as Mr. Combs’s sexual exploitation of women.

The role of Mr. Combs’s associates matters much because by charging him with running a criminal enterprise, the government, under federal racketeering law, has been able to accuse him of crimes for which the statute of limitations has long expired. If convicted as a racketeering kingpin, Mr. Combs could face a sentence of possibly life in prison.

At least one former employee of Mr. Combs is expected to take the stand against him, according to prosecutors. A witness list for the case has not been publicly disclosed, though prosecutors said in a filing that they intend to introduce “statements” from what they described as a range of former employees, and the jury is expected to see text messages and voice recordings that prosecutors will argue help prove a criminal conspiracy.

Mr. Combs, who is known as Diddy and Puff Daddy, has pleaded not guilty to all of the charges against him. His lawyers have asserted that the sex at the heart of the government’s case was entirely consensual. And they have objected to the broad scope of the prosecution, saying that the government has used federal racketeering law to essentially construe Mr. Combs’s entire adult life as a criminal enterprise.

“All the government really seeks to do is show that Mr. Combs is a violent, dangerous, and deviant person who deserves to be locked up regardless of whether it can actually prove the somewhat technical elements of the charged offenses beyond a reasonable doubt,” the defense wrote in court papers.

The primary federal racketeering law that underpins the case — called the Racketeer Influenced and Corrupt Organizations Act, or RICO — was passed by Congress in 1970 with a specific aim: to combat the Mafia.

But in the decades since, its scope of targets has grown.

Racketeering laws have been used to prosecute Wall Street and pharmaceutical executives, street gang members, rappers, and the mastermind of a college admissions cheating scheme.

In the wake of the #MeToo movement, they have been used to prosecute a series of high-profile men accused of sexual abuse, including the singer R. Kelly and Keith Raniere, the Nxivm sex cult leader.

“You wouldn’t have seen it 50 years ago being used against someone like Diddy, but today, nobody blinks,” said Gordon Mehler, a defense lawyer and former federal prosecutor.

One advantage in pursuing a racketeering case is that it allows prosecutors to present a sweeping narrative that includes accusations about a defendant’s misdeeds stretching back decades.

In Mr. Combs’s case, those include allegations that in 2011 he executed a scheme to break into a rival’s home and then his “co-conspirators” set the rival’s car on fire weeks later with a Molotov cocktail, as well as accusations that he dangled a woman off a balcony after she witnessed his abuse.

“They can try to sweep in all of his bad behavior over decades and claim that it’s part of the charged conspiracy,” said Marc Fernich, a lawyer who has long defended people charged in racketeering cases.

It is more common, legal experts say, for racketeering prosecutions to target multiple defendants. In the case against Mr. Raniere, for example, three women associated with his cult pleaded guilty to racketeering conspiracy ahead of his trial.

But there have been other racketeering cases pursued against a single defendant, including the prosecution of Mr. Kelly.

He was found guilty in 2021 of serving as the ringleader of a decades-long scheme to recruit women and underage girls for sex.

The government argued that Mr. Kelly’s employees were core to this scheme: They handed his phone number to girls at concerts, arranged for their travel to see him and stood guard when the singer confined them as punishment.

Some of Mr. Kelly’s employees faced criminal charges outside the scope of that trial, but none were charged with racketeering.

“Having that second or third or fourth person at the table can end up being a distraction for both the prosecutors and the jury,” said Elizabeth Geddes, a former prosecutor who tried the case against Mr. Kelly.

In the seven months since Mr. Combs’s arrest, the government’s case against him has been quietly expanding. But no additional defendants have been named, spurring public curiosity over who, exactly, are the other members of the alleged conspiracy.

“I don’t think I’ve ever seen anything like this,” the comedian Dave Chappelle joked on “Saturday Night Live” this year. “They’ve got this guy in a RICO case, by himself.”

Not all employees of Mr. Combs will be cast by the government as collaborators. Some are simply being treated as witnesses. Others have been cast by the government as victims who were forced to work long hours, and with little pay, while enduring physical and verbal abuse by Mr. Combs.

One witness is expected to be Mr. Combs’s former personal chef, Jourdan Cha’Taun, who shared her allegations of abusive working conditions in a recent documentary series, “The Fall of Diddy.” She said in the series that working for Mr. Combs was so stressful that she suffered hair loss, and that after she quit, Mr. Combs berated her and shoved her to the ground.

“Puff scared me,” she said in the series. (In court papers, Mr. Combs’s lawyers accused the chef — referred to in public filings as “Individual A” — of having “bias and animosity” against Mr. Combs.)

Another former employee who is cooperating with the government has also accused Mr. Combs of coercing her into sex. She is one of four women at the core of the government’s sexual exploitation case against Mr. Combs.

The trial’s star witness is expected to be Casandra Ventura, Mr. Combs’s former longtime girlfriend who sued him in 2023, accusing him of years of physical and sexual abuse. The lawsuit was quickly settled, but it spurred dozens of civil suits that alleged misconduct and set in motion the criminal investigation that led to his indictment.

Ms. Ventura, a singer who is also known as Cassie, is expected to testify about sexual encounters known as “freak-offs,” that Mr. Combs directed, filmed and masturbated during.

The prosecution has argued that some of those encounters, which investigators said included male prostitutes, amounted to sex trafficking, citing repeated physical abuse of Ms. Ventura as “one of numerous ways that he controlled her and led her to believe that she had no choice but to do his bidding.”

The defense has insisted that Ms. Ventura was a willing participant and has accused the prosecution of seeking to police a common lifestyle that involves sex outside the relationship. “Call it ‘swingers,’ call it whatever you will,” said Marc Agnifilo, Mr. Combs’s lead lawyer, at a hearing last month.

A key point of dispute at trial will be over the harrowing events that unfolded in 2016, when Mr. Combs was captured on surveillance footage striking, kicking and dragging Ms. Ventura down a hotel hallway.

The government has argued that the assault is clear evidence of sex trafficking: that Mr. Combs beat Ms. Ventura as she left the site of a freak-off. Afterward, prosecutors have said, Mr. Combs bribed hotel security with $100,000 to obtain the footage and cover up the crime, and his employees kept in touch with Ms. Ventura to make sure she did not report the assault to police.

“You are sick for thinking it’s OK to do what you’ve done,” Ms. Ventura texted Mr. Combs after the assault, according to prosecutors.

The defense has argued that the assault had nothing to do with sex, but was actually about a dispute over infidelity.

Apart from Ms. Ventura, prosecutors have accused Mr. Combs of sex trafficking two other women, whose names have not been revealed publicly. They say he coerced them into sexual encounters — either with him or with male prostitutes — that could last for hours, and sometimes full days without sleep.

The defense has described the women as former long-term girlfriends of Mr. Combs. One of them, prosecutors said, was receiving money from him as recently as September, around the time he was arrested.

The sex trafficking charges are intertwined with the government’s overarching racketeering case. According to the prosecution’s theory of the case, Mr. Combs’s employees were tasked not just with running his life and business but with fulfilling Mr. Combs’s sexual desires — and protecting his reputation by concealing his abusive conduct.

“The defendant demanded loyalty from his victims,” prosecutors wrote in court papers, “as well as all members and associates of the Combs Enterprise.”