Diddy Prosecutors May Face Uphill Battle on Key Racketeering Charges, Expert Says: 'Everything Described Is Deviant and Appalling, But Not Criminal'

The federal trial of Sean "Diddy" Combs entered its fifth week on Monday. Still, legal experts said prosecutors could face challenges in proving the most serious charge against him: racketeering conspiracy.

Testimony in the courtroom has been searing and graphic, with accusers describing years of abuse, coercion, and manipulation.

But legal hurdles are high for prosecutors trying to make a case that Combs ran some crime syndicate, experts say, despite the fact that the music impresario faces charges he shot up a crowded nightclub with a stolen gun.

"Everything that's been described by Cassie is deviant and appalling, but it's not necessarily criminal," said criminal defense attorney Joshua Ritter in an interview with Us Weekly.

Star Witness Testimony and Legal Limits

Cassie Ventura, Combs' ex-girlfriend and the prosecution's key witness, testified in May about being forced into "freak offs," sexual encounters with male escorts while Combs watched. She also recounted being beaten and dragged in a hotel hallway, a 2016 incident corroborated by surveillance footage presented in court.

While the jury has heard harrowing details of the former couple's 11-year on-and-off relationship, Ventura's allegations of abuse are not the central focus of the charges.

"Both sides agree there was domestic violence," said Kelly Hyman, a human trafficking attorney and host of the podcast "Unresolved – The Diddy Cases." "But Diddy hasn't been charged with that."

Instead, Hyman said the defense is portraying Ventura and other accusers as willing participants. She noted that the defense claims the relationship was "jealousy-fueled" and "consensual," and that the conduct described doesn't meet the legal threshold for racketeering or sex trafficking.

"If these individuals were willing participants, then we really don't have the elements of a crime here," Ritter added.

Combs' legal team has used texts, social media posts, and emails from accusers, including a former assistant who went by the pseudonym "Mia," to challenge their credibility. Defense attorneys pointed out that Mia, who testified Combs raped her multiple times between 2009 and 2017, once posted online praising him and sent him messages expressing affection.

Mia said she had been "brainwashed" and was afraid of his "power and wrath."

Focus Turns to Racketeering Evidence

The racketeering charge hinges on proving that Combs led a criminal enterprise engaged in offenses such as arson, sex trafficking, extortion, bribery, and obstruction of justice. Experts say that remains a significant burden.

"Based upon Cassie's testimony, we don't really see the elements of the racketeering, which would involve a criminal enterprise," Ritter said.

To secure a conviction, prosecutors must establish a link between Combs and other individuals committing crimes under his direction. So far, no witnesses have claimed he explicitly ordered any crimes.

"They're definitely going to have to have other witnesses testify to how others were participating in this criminal enterprise," said Ritter.

However, there have been some allegations suggesting potentially criminal behavior. Ventura's mother, Regina Ventura, testified that she paid Combs $20,000 to stop him from releasing a sex tape. Former hotel security officer Eddy Garcia also said he accepted $100,000 from Combs in exchange for footage showing him assaulting Ventura.

Another witness, Capricorn Clark, testified that Combs forced her to accompany him to rapper Kid Cudi's home, where he allegedly intended to harm Cudi over a relationship with Ventura. Clark claimed Combs threatened to kill her if she spoke about the incident. During cross-examination, however, the defense stated that Clark had previously told them she went with Combs voluntarily to prevent him from acting "stupid." Clark said she did not recall making that statement.

Cudi confirmed that his home was not damaged and that his door had been left unlocked.

TV journalist and attorney Megyn Kelly also questioned the legal strength of the case.

"We're really growing to loathe [Diddy] progressively every day, but that doesn't necessarily mean these are crimes," Kelly said on "The Ben Shapiro Show."

The 55-year-old is charged in federal court with five federal charges, including one count of racketeering conspiracy, which carries a maximum possible sentence of life imprisonment, along with two counts of sex trafficking by force, fraud, or coercion, and two counts of transportation to engage in prostitution.

Tags

Diddy, Diddy Trial