Diddy Trial: From RICO Charges to 'Freak Offs'

The trial of Sean “Diddy” Combs, set to begin with jury selection on Monday in New York City, is a high-profile federal case involving charges of racketeering conspiracy, sex trafficking, and transportation to engage in prostitution. Key elements, include RICO charges, the Cassie Ventura surveillance tape, the “Freak Offs,” and other critical aspects of the case, drawing from available information.

Sean Combs known by aliases like Puff Daddy, P. Diddy, and Love, faces a federal indictment unsealed in September 2024, accusing him of running a criminal enterprise through his entertainment empire, including Bad Boy Records, for his “sexual gratification” over decades. The charges include:

Racketeering Conspiracy (RICO): Prosecutors allege Combs led a racketeering conspiracy from 2008 to 2024, engaging in sex trafficking, forced labor, kidnapping, arson, bribery, and obstruction of justice. The Racketeer Influenced and Corrupt Organizations Act (RICO), typically used against organized crime, is applied here to frame Combs’ alleged activities as a coordinated criminal enterprise involving his businesses and employees.

Sex Trafficking by Force, Fraud, or Coercion: Combs is accused of using force, fraud, or coercion to recruit and transport women across state lines for prostitution, particularly in events called “Freak Offs.” A third superseding indictment added a sex trafficking charge related to “Victim-2” for activities between 2021 and 2024.

Transportation to Engage in Prostitution: This charge involves allegations that Combs arranged for victims and sex workers to travel for “Freak Offs,” with his staff facilitating logistics and payments.

If convicted, Combs faces a minimum of 15 years and up to life in prison. He has pleaded not guilty to all charges and denied civil allegations, with his legal team asserting that his sexual encounters were consensual and part of a “swinger” lifestyle.

Casandra “Cassie” Ventura, a singer and Combs’ former girlfriend of over a decade (2007–2018), is central to the case as “Victim-1” and a key witness who will testify under her real name. Her allegations sparked the legal scrutiny that led to Combs’ indictment:

In May 2024, CNN released hotel security footage from March 5, 2016, showing Combs kicking, dragging, and throwing a vase at Ventura in a Los Angeles hotel hallway. The video corroborated an incident described in her lawsuit and the indictment. Combs issued a public apology, calling his behavior “inexcusable” and stating he sought therapy and rehab, but his legal team later argued the video was part of a consensual, complex relationship and accused the Department of Homeland Security of leaking it to prejudice the case. Judge Arun Subramanian ruled on April 25, 2025, that the video is admissible, rejecting defense claims of manipulation, as CNN denied altering the footage.

“Freak Offs” are described by prosecutors as “elaborate and produced sex performances” orchestrated by Combs, often lasting days, involving female victims and male sex workers. 

These events allegedly involved drugs like cocaine, methamphetamine, ecstasy, ketamine, and GHB to keep participants “obedient and compliant.” Combs is accused of directing, masturbating during, and recording the acts, using the footage to ensure victims’ silence. His staff reportedly booked hotel suites, arranged travel, stocked supplies (e.g., drugs, baby oil, lubricants), and provided IV fluids for recovery from physical exertion and drug use.

Even if acquitted, Combs’ reputation and business empire, once valued at over a billion dollars, are severely damaged. His legal team has rejected plea deals, signaling a fight to clear his name, but civil lawsuits could still result in significant financial penalties. The trial’s outcome will likely hinge on the credibility of Ventura and other witnesses, the interpretation of “Freak Off” videos, and whether jurors view Combs’ actions as consensual or coercive.