Did federal prosecutors prove their case against Sean ‘Diddy' Combs? Legal experts weigh in

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Whether prosecutors in the trial of Sean 'Diddy' Combs have proven their case is a question that will be answered by his jury, which soon will start deliberating in the hip-hop mogul's blockbuster sex trafficking trial after hearing from 34 witnesses in testimony over more than six weeks.
A conviction certainly is not assured, with lawyers and legal analysts saying there is ample room for jurors to find reasonable doubt – particularly on the racketeering conspiracy and sex trafficking charges.
'This is not a walk in the park case; this is not a home run, at all,' said trial attorney and legal analyst Misty Marris. 'There are a lot of technicalities where I think the prosecution case has vulnerabilities.'
Federal prosecutors allege Combs and some of his closest employees comprised a criminal enterprise that used threats, violence, forced labor and bribery to force his ex-girlfriends Cassie Ventura and 'Jane' – a pseudonymous accuser – to participate in sexual acts called 'Freak Offs' or 'hotel nights,' and to protect his reputation.
Those allegations encompass the charge of racketeering conspiracy. Combs also is charged with two counts of sex trafficking Ventura and Jane and two counts of transporting the women and male escorts for the purposes of prostitution. He has pleaded not guilty to all charges. If convicted of the most serious charges, Combs could face up to life in prison and a minimum sentence of 15 years.
While the evidence supporting charges of transporting people for prostitution is relatively straightforward, it remains to be seen whether prosecutors have effectively linked Combs' alleged criminal activity to an enterprise – and indeed proven such an enterprise existed, legal analysts said. And accusations of sex trafficking and the case more broadly have been undercut by the defense's contention that these acts, while perhaps unseemly, were consensual and separate from his lawful businesses, the analysts said.
'Was (Combs) running a criminal enterprise?' asked CNN legal analyst Joey Jackson. 'Or was he running a legitimate, iconic business that was overwhelmingly successful, and he was just a very flawed and broken person who was doing some personal things on his personal time, and not using an organization to further criminality?'
'Those are the competing narratives in the courtroom.'
Prosecutors' toughest challenge will likely be securing a conviction on the racketeering conspiracy charge, experts agreed, citing its complexity and the novelty of its application in the Combs case.
The charge stems from the Racketeer Influenced and Corrupt Organizations Act, or RICO, which was created to prosecute organized crime, like the mafia. Any racketeering case is focused on a so-called 'enterprise,' or a group of people engaged in the alleged misconduct.
To secure a conviction, prosecutors must prove Combs and at least one other person committed at least two crimes known as 'predicate acts' within a 10-year window to further the enterprise. They specifically sought to prove transportation for purposes of prostitution, witness tampering, bribery, forced labor and drug-related offenses, but on Wednesday indicated they would not argue attempted arson and attempted kidnapping, according to a letter prosecutors submitted to the judge.
Combs has been charged alone, despite prosecutors alleging the enterprise included Combs and members of his inner circle, including his bodyguards and high-ranking employees.
In fact, jurors did not hear directly from many of these people – and that will be 'one of the biggest uphill battles for this particular prosecution,' said CNN anchor and chief legal analyst Laura Coates.
For example, prosecutors have referred to Combs' former chief of staff, Kristina Khorram, as 'an agent and co-conspirator' of the defendant. Though she was mentioned by multiple witnesses and her messages with Combs were presented in court, she was not called to testify. Khorram has denied wrongdoing, and her attorney has not responded to CNN's requests for comment throughout the trial.
'The absence of that testimony does leave some room for a seed of doubt to be planted that the defense will undoubtedly exploit,' said Coates, who hosts the CNN podcast 'Trial By Jury: Diddy.'
In a typical RICO prosecution, one might expect to see multiple defendants, like a mobster and his underbosses, Jackson said. But that's not the case in Combs' trial. Prosecutors have suggested employees obtained drugs, baby oil and arranged hotel rooms and flights.
'The issue for that is going to be, were they really aware?' he said. 'You could be an employee getting baby oil, you can be an employee getting hotel rooms … Do you know what your boss is doing, or do you do what you're told?'
To convict Combs of the two sex trafficking charges – one each for Ventura and Jane – jurors must find that prosecutors proved he compelled them to participate in commercial sex acts through force, fraud or coercion.
Some of these elements are evident, the legal experts indicated. In Ventura's case, physical force was viscerally illustrated by the InterContinental Hotel surveillance footage showing Combs assault Ventura in 2016 – first published by CNN. Physical violence was constant throughout Ventura and Combs' 11-year relationship, according to Ventura's testimony and that of other corroborating witnesses, who told the jury they witnessed Combs assaulting Ventura on numerous occasions.
The jury also saw photographs of bruises and gashes on Ventura's body, which were injuries she testified she sustained on dates separate from the 2016 hotel incident. Prosecutors worked to use that evidence to establish a pattern of physical violence they argue shows she was forced and coerced into 'Freak Offs.'
In the cases of both women, experts said, there was a degree of financial coercion: Aside from being his girlfriend, Ventura was signed to Combs' Bad Boy record label when she was 19 years old, and he wielded great power over her career. Jane, meanwhile, testified she and Combs entered into a 'love contract' where he agreed to pay her $10,000 rent, but that he threatened to cut her off financially if she stopped participating in 'hotel nights.'
Marris believes the sex trafficking case for Ventura is stronger, she said, pointing to the video and Combs' control over her professional career. Combs had also allegedly threatened to release sexually explicit videos of Ventura, and her mother testified she wired $20,000 to Bad Boy Entertainment out of fear for her daughter's safety. The money was later returned, she said.
Still, the prosecution will face another challenge: Combs' defense leveraged the women's testimony and text messages with the defendant to undermine the suggestion of coercion, and they pointed out both women at times helped coordinate the sexual encounters, texting with escorts and buying supplies for the room. Both women said during their testimony they were asked by Combs to make these arrangements.
The jury also saw text messages between Combs and male escorts arranging their travel, and Combs and his employee booking flights, as well as American Express and bank statements tied to those expenses, indicating Combs paid the bills.
Jane expressed in some messages she did not want to participate in 'hotel nights,' but she would acquiesce and testified she wanted to make Combs happy. And she admitted on the stand Combs continues to pay her for rent and her legal representation to this day, even as she testifies against Combs, who is being held in the Metropolitan Detention Center in New York.
Texts showed Ventura at times expressed a willingness to participate in the 'Freak Offs,' and that her relationship with Combs was at times loving: 'I'm always ready to Freak Off lolol,' she wrote in August 2009, toward the beginning of their relationship.
In March 2017 she said she enjoyed the encounters 'when we both want it.' But, she testified, 'I would say that loving 'Freak Offs' were just words at that point.'
'The text messages are really the star of the show in this case,' Marris said. 'Text messages that Cassie exchanged with Combs at the time are really important for the defense and do undercut the prosecution narrative and their argument.'
Establishing Combs as a horrible and abusive romantic partner, she said, is not enough to prove sex trafficking: Indeed, the defense on Tuesday acknowledged Combs' and Ventura's relationship was 'toxic for many reasons' but argued domestic violence is not sex trafficking.
Prosecutors tried to combat this idea through psychologist Dawn Hughes, who offered context to the behavior of victims of abuse. Hughes had not assessed the victims or witnesses in Combs' case but testified it's common for victims to remain in abusive relationships. Financial dependence, she said, also plays an important role – and sexual abuse can make it difficult to seek help and leave.
Experts largely agreed the two charges of transportation for the purposes of prostitution, stemming from the Mann Act, are likely the easiest for the prosecution to prove, with clearer evidence and less ambiguity than the others.
'That has been proved by leaps and bounds by prosecutors,' said Marris, adding: 'It's truly very simple: Did individuals cross state lines with the intent to engage in prostitution?'
Jane testified she and Combs had 'hotel nights' between May 2021 and October 2023 in a variety of locales, including Los Angeles, New York, Miami and Turks and Caicos. Similarly, Ventura said 'Freak Offs' were held in some of those locations and other cities, like Atlanta and Las Vegas.
Ventura testified some escorts participated in 'Freak Offs' in multiple states. They were paid between $1,500 and $6,000 afterwards in cash provided by Combs, she said. Her testimony was bolstered by various records presented in court, including flight records, American Express charges and hotel invoices.
The jury also watched sexually explicit video footage of Ventura and Jane engaging in sexual acts with male escorts. The videos line up with the dates of many flight records and hotel invoices.
'They've got the names of the people,' Jackson said. 'They've got the hotel records. They know that they were commercial sex workers or escorts. That's more clear cut.'
The defense has argued there's not sufficient evidence that the escorts and entertainers were paid for prostitution as opposed to for their time.
The defense rested its half-hour case Tuesday, calling no witnesses. But Combs' attorneys have been laying out their case all along, through the cross-examination of the government's witnesses. Combs did not testify.
'The defense does not have the burden (of proof), and they are 1,000% aware of it,' Coates said. 'And they're trying to capitalize on what they don't have to prove.'
'Overall, their theme has been, this is a money grab, full stop. There are people who have free choice and free will and they exercised it,' she said, channeling the defense theory.
Ventura filed a lawsuit against Combs in November 2023, alleging he assaulted, raped and sex trafficked her. Combs denied wrongdoing, but they settled the lawsuit a day later – for $20 million, Ventura testified.
'I'd give that money back if I never had to have 'Freak Offs,'' she testified on redirect. Crying, she added, 'If I never had to have 'Freak Offs' I would have had agency and autonomy.'
A friend of Ventura's, Bryana Bongolan, had also testified about an encounter with Combs in which he allegedly physically assaulted and threatened her, claiming he dangled her over the balcony railing at Ventura's apartment. Bongolan, too, has filed a lawsuit against Combs seeking $10 million.
The defense has tried to use these and other civil lawsuits against their client 'as their star witness,' Coates said. 'They have painted this case as jealous money grabs – and kinky, not criminal.'
CNN's Kara Scannell, Elizabeth Wagmeister, Lauren del Valle, Nicki Brown, Laura Dolan and Eric Levenson contributed to this report.