Having spent eight years as a federal prosecutor, I can tell you the government typically doesn’t take a case unless they’re convinced the case is watertight.
So, when the Feds threw the book at Sean ‘Diddy’ Combs, accusing him of crimes that carry a life sentence, I assumed that they had the goods on him. After all, federal prosecutors have a 90 percent conviction rate.
But now, nearly four weeks into the Manhattan federal court proceedings, I’m starting to suspect that the 55-year-old hip hop mogul may very well walk away a free man.
Combs has pleaded not guilty to all the charges against him – one count of racketeering conspiracy (a coordinated effort to profit from a criminal scheme), two counts of sex trafficking and two counts of transporting individuals across state lines for the purposes of prostitution.
But it is critical to understand that Combs is not being prosecuted for being a terrible person, a domestic abuser, a pervert or even a monster. Indeed, in her opening statements, Combs’ defense attorney conceded that her client is an objectively bad person, who lied and cheated on multiple partners, ‘has a bad temper,’ and ‘when he drank or did the wrong drugs, he got violent.’
‘We take full responsibility that there was domestic violence in this case,’ said attorney Teny Geragos. But, she stressed, ‘domestic violence is not sex trafficking.’ And she’s right. Nor is it racketeering conspiracy.
Combs is being accused of crimes, the specific elements of which must be demonstrated beyond a reasonable doubt to a jury of his peers, in order to secure a conviction. And the prosecution’s task is more difficult than that, for if just one of 12 jurors on this case decides that they cannot convict Combs on a charge, then he gets off, at least for the time being and barring a retrial.
It is with this understanding of the legal system that I listened to the testimony of the prosecution’s star witness, Cassie Ventura, Combs long-suffering partner, who dated him until October 2018.
Sean ‘Diddy’ Combs (pictured in 2018) is not being prosecuted for being a terrible person, a domestic abuser, a pervert or even a monster. Combs’ defense attorney conceded that her client is an objectively bad person, who cheated on multiple partners and ‘has a bad temper.’
‘We take full responsibility that there was domestic violence in this case,’ said Diddy’s attorney Teny Geragos (depicted here in a court sketch). But, she stressed, ‘domestic violence is not sex trafficking.’ And she’s right. Nor is it racketeering conspiracy.
Her terrible story became known to the world when security camera video of Combs viciously beating her in the hallway of a California hotel in 2016 was released last year. And hers was surely the testimony that prosecutors would have wanted ringing in jurors’ ears as they closed their case, but they were forced to call the eight-months pregnant Ventura to the stand, more than three weeks ago, on just the second day of the trial.
Almost two weeks after her testimony, she gave birth to her third child.
Softly spoken and at times tearful, Ventura was, without a doubt, a sympathetic figure on the stand, but almost immediately, her testimony played into the defense strategy.
Predictably, from the very start, the defense has claimed that Combs’ sexual encounters – while bizarre and often violent – were consensual.
Ventura gave conflicting accounts saying, on one hand, that she lived in fear of Combs while, on the other, she loved him.
The defense then brought up a litany of text messages and emails that suggested Ventura was enthusiastic about sordid orgies arranged by Combs that he called ‘Freak Offs’.
‘I’m always ready to freak off LOLOL,’ she said in one message that she read aloud in court.
The prosecution also called a male escort, Sharay Haynes, known in the exotic dancing industry as ‘The Punisher,’ to the stand.
He said that he had once urinated in Ventura’s mouth during a ‘freak off.’ Ventura said she felt ‘humiliated’ by the act. But, under cross-examination, Haynes claimed Ventura had ‘coached’ him through it and said he saw no signs that she was uncomfortable or coerced.
Haynes also said that it was Ventura, not Combs, who orchestrated their encounters, while the hip-hop mogul watched, masturbated and gave directions.
Cassie Ventura, Combs long-suffering partner who dated him until October 2018 is the prosecution’s star witness. (Pictured: Diddy and Cassie at her 21st birthday party in 2007).
Again and again, the prosecution has called witnesses, suggesting that they were going to deliver the smoking gun proof of Combs’ guilt only for their testimony to fall short.
Last week, the rapper Kid Cudi – whose legal name is Scott Mescudi – testified about Combs’ alleged threatening behavior during a period that Mescudi had a brief relationship with Ventura.
He told jurors that he suspected Combs had broken into his home (a claim corroborated by another witness) and that Combs had coordinated the firebombing of Cudi’s Porches sports car. But Mescudi had no evidence, other than his suspicions.
On May 20, a special agent from United States Homeland Security Investigations testified that federal officers recovered two AR-15 assault-style rifles with defaced serial numbers and piles of pills, marijuana and other drugs from Combs’ Miami Beach enclave of Star Island in March 2024.
Prosecutors have alleged these weapons and intoxicants were used to make women compliant during freak-offs. But again, there was no clear evidence of their claims.
And on Friday, a former Combs’ assistant – only referred to by the pseudonym ‘Mia’ to shield her identity – testified that Combs sexually assaulted her multiple times, including a few months into her employment with him, from 2009 until 2017.
When she was asked why she didn’t leave Combs and his company, she said the thought didn’t occur to her at the time.
Understandably, the prosecution brought in an expert witness, a psychologist, to attempt to explain why Ventura and others stayed with Combs even as he was abusive to them.
‘It’s hard for us to break up with someone under the best of circumstances,’ said psychologist Dawn Hughes. ‘When you have all this violence and abuse, you’re just trying to live day to day,’ she said, revealing that victims often feel form an ‘intense psychological bond’ with their abusers.
Again and again, the prosecution has called witnesses, suggesting that they were going to deliver the smoking gun proof of Combs’ guilt only for their testimony to fall short. (Pictured: Diddy making a heart symbol as he enters the courtroom).
But I expect the defense to bring in an expert witness of their own to rebut Hughes. And typically, when a jury hears conflicting expert testimony, they discount both and rely on the witnesses’ statements, which in this case are problematic for the prosecution.
And what of these jurors?
The jury is majority male, consisting of eight men and four women. That too, weighs in the defense’s favor.
In my experience, and especially in the case of sex crime trials, men are more likely than women to be skeptical of female accusers. They’re more easily convinced that alleged victims were actually willing participants, who are now weaponizing their experiences in pursuit of some purpose other than the truth.
This leaves the trial very much in the air.
The racketeering case is so far entirely unmade, the sex trafficking case is weak and the allegations of transportation of an individual for prostitution are the thinnest of the lot.
To be sure, there’s still time for the prosecution to make up for the flaws in their case, but the clock is ticking.
And if a jury were to vote today, in my mind, they wouldn’t only struggle to convict… they shouldn’t.
