Why Legal Experts Believe Diddy Could Still Go Free, Even After Explosive Trial Revelations (Exclusive)

Over the course of four weeks, witnesses for the prosecution in the trial against Sean “Diddy” Combs have painted a picture of a monster — an abusive figure fixated on power and control, willing to do whatever it takes to bend victims to his will. His ex Casandra “Cassie” Ventura, then eight months pregnant, tearfully recalled being beaten and forced to have sex with male escorts for days on end. A former assistant claimed Diddy raped her multiple times. Another former employee said he kidnapped her at gunpoint, and rapper Kid Cudi testified that Diddy broke into his house and set his Porsche on fire after discovering he’d been involved with Ventura.

There’s no doubt the allegations are shocking and disturbing. However, it’s less certain whether or not they’re enough to convict the disgraced music mogul, 55. Diddy was arrested in September and faces five federal charges: one count of racketeering conspiracy, which carries a maximum sentence of life in prison; two counts of sex trafficking by force, fraud or coercion, which carries a maximum sentence of life in prison and a minimum sentence of 15 years; and two counts transportation to engage in prostitution, which carries a max sentence of 10 years in prison. (He has denied all charges.) Upon Diddy’s arrest, his lawyer Marc Agnifilo told Us Weekly in a statement that the father of seven “is an imperfect person but is not criminal.”

The prosecution has to prove beyond a shadow of a doubt that Diddy is the leader of a criminal enterprise whose members engaged in sex trafficking, forced labor, arson, bribery and obstruction of justice through the use of violence, threats and coercion. It’s going to be a heavy lift, says criminal attorney Joshua Ritter. “Everything that’s been described by Cassie is deviant and appalling, but it’s not necessarily criminal,” he tells Us. TV journalist and lawyer Megyn Kelly expressed similar thoughts during an appearance on commentator Ben Shapiro’s show on May 31, saying in part, “We’re really growing to loathe [Diddy] progressively every day, but that doesn’t necessarily mean these are crimes.”

Ventura, 38, was the prosecution’s star witness, and she delivered searing testimony detailing her toxic 11-year on-and-off relationship with Diddy while on the stand in May. She shared graphic details of “freak offs” in which she claimed she was forced to have sex with male escorts while Diddy watched. She also described ruthless beatings at the hands of Diddy, and on May 14, jurors were shown video footage from 2016 of the rapper kicking and dragging her in a hotel lobby after she tried to escape a freak off.

But legal experts note Diddy isn’t on trial for domestic violence. “Both sides agree there was domestic violence,” says human trafficking attorney Kelly Hyman, host of true-crime podcast Unresolved – The Diddy Cases, “but Diddy hasn’t been charged with that.” Hyman tells Us the defense claims that while it did take place, Ventura and Diddy’s relationship was “jealousy-fueled” and “consensual” and that his behavior doesn’t meet “the charges of racketeering co-conspiracy [or] sex
trafficking.”

The defense is trying to prove that many witnesses who testified against Diddy consented to his actions. A former personal assistant of Diddy’s, going by the pseudonym “Mia,” alleged he sexually assaulted her multiple times between 2009 and 2017. During cross-examination, Diddy’s lawyers pointed out that Mia had shared several glowing social media posts about her boss and sent him texts saying Mia loved him (she told jurors she’d been “brainwashed” by Diddy and she was frightened of “his power and wrath.”)

Another former employee, Capricorn Clark, claimed Diddy took her against her will to rapper Kid Cudi’s home to “kill” Cudi over his romance with Ventura. Clark said Diddy threatened to “kill” her if she told authorities that he’d been inside Cudi’s home. Attorneys for Diddy portrayed the kidnapping ordeal as consensual, with Agnifilo stating she told him during a 2024 meeting that she voluntarily chose to accompany Diddy to prevent him from doing “something stupid.” (Clark claimed she did not recall saying that.) Under cross-examination, Cudi acknowledged that he had left his door unlocked and that his home was not damaged.

The defense also pointed to Ventura remaining with Diddy for more than a decade and noted texts and emails in which she expressed enthusiasm about freak offs. On Shapiro’s show, Kelly said the defense “is trying to show [Cassie] was a willing participant … and that one of the reasons she didn’t leave … was she enjoyed the lifestyle.” Says Ritter: “If these individuals were willing participants, then we really don’t have the elements of a crime here.”

Legal experts say the prosecution has yet to make much headway on the count of racketeering. “Based upon Cassie’s testimony,” says Ritter, “we don’t really see the elements of the racketeering, which would involve a criminal enterprise.” Both Ritter and Hyman say that will likely be the focus as the trial continues (it’s expected to last eight weeks).

For those charges to stick, there has to be a predicated crime, like arson, sex trafficking or extortion. Ventura’s mom, Regina Ventura, testified that she paid Diddy $20,000 after he threatened to release a sex tape of her daughter, and on June 3, Eddy Garcia, a former security officer at the hotel where Diddy assaulted Ventura, said Diddy gave him $100,000 in cash in exchange for footage of the altercation.

In earlier courtroom appearances, one former employee testified that he bought drugs for Diddy and drove the rapper — who was armed with guns at the time — to confront his rival Marion “Suge” Knight. “They’re definitely going to have to have other witnesses testify to how others were participating in this criminal enterprise,” Ritter predicts. “So far, no one has taken the witness stand and said, ‘Diddy ordered me… to go in there and commit arson,’ ” says Hyman, “but there are [many] more weeks to go. The prosecution is building their case brick by brick.”

Regardless of the verdict, Diddy will still have to contend with over 70 civil sexual assault lawsuits that have been filed against him since November 2023. His legal team has consistently denied the allegations.

In December, a source told Us Diddy was spending much of his time at the Brooklyn Metropolitan Detention Center “preparing for his defense and trying to stay positive.” Even now, he appears hopeful. An eyewitness who’s been attending the trial tells Us the rapper seemed to be in good spirits on May 27. Upon walking in, he immediately looked at the two back rows of public attendees — consisting mainly of fans and journalists — slightly bowed and put his hand on his chest in a signal of gratitude. “This gesture,” says the eyewitness, “has become a commonplace habit.”

If you or someone you know has been sexually assaulted, contact the National Sexual Assault Hotline at 1-800-656-HOPE (4673). If you or someone you know is experiencing domestic violence, please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support. If you or someone you know is a human trafficking victim, contact the National Human Trafficking Hotline at 1-888-373-7888.