INTRODUCTION
After being indicted on September 17th, 2024, Sean ‘Diddy’ Combs, a household name in hip-hop and a three-time Grammy Award winner, faces a sex trafficking, racketeering, conspiracy, and prostitution trial on May 5th, 2025 (ABC News; United States of America v. Sean Combs). Prosecutors say he orchestrated a decades-long “criminal enterprise” where he and others forced women into sexual encounters with prostitutes, called “freak-offs,” through the use of drugs along with physical and sexual abuse. Diddy pleaded not guilty and his defense attorneys proposed a $50 million bail package that the judge denied (AP News).
While we wait for his trial to start, let’s take a moment to learn about Diddy’s history and jail protocols, with insight provided by Joseph E. Gunja, an Experts.com member and Jails—Prison—Correctional Facilities expert.
BACKSTORY: DIDDY’S PAST ALTERCATIONS
TIMELINE
Throughout his career, Diddy has been associated with a slew of violence and grave misbehavior. He was not charged for some of these situations. However, here are some examples of his most notable misconduct from a timeline provided by Rolling Stone:
- 1991 CCNY Tragedy: A celebrity basketball game Diddy co-promoted at City College of New York ended in 9 deaths and 29 injuries. The number of attendees exceeded the capacity limit, and the security he hired could not manage the crowd. As a result, Combs settled numerous lawsuits from the victims’ families from 1991-2000.
- 1998 Steve Stoute Attack: Stoute accidentally sent MTV a version of the “Hate Me Now” music video depicting Combs as Jesus Christ being crucified. Combs wanted the scene deleted and was angry that it aired. He and two other men attacked Stoute with a champagne bottle. Along with attending a one-day anger management session, he received second-degree assault and criminal mischief charges.
- 2019 Gina Huynh Claims Abuse: Combs’ ex-girlfriend Gina Huynh reported to Tasha K, a blogger, that Diddy physically assaulted her during their five-year relationship. For example, she stated he stomped her stomach and punched the back of her head. Huynh also told Tasha K that Diddy’s circle perpetuated the abuse and did nothing to stop it.
At this point, Combs has not faced any significant consequences for his actions. However, that all changed in 2023.
KEY MOMENTS LEADING TO THE DIDDY TRIAL
On November 16th, 2023, Combs’ ex-girlfriend, Cassandra “Cassie” Ventura, filed a federal lawsuit against him. The lawsuit detailed physical abuse, intimidation, coerced sex with male escorts while he watched, and rape in 2018. Ventura added another accusation that Combs was responsible for causing Kid Cudi’s car, another famous rapper, to explode back in 2012 to prevent him from pursuing Ventura romantically. Kid Cudi validated the allegation (New York Times). To counter Ventura, Combs claimed she attempted to blackmail him for $30 million before the lawsuit. He and Ventura settled for an unknown amount the following day. Undoubtedly, her lawsuit catalyzed other women, colleagues, and critics to share their stories and corroborate his misdeeds (Billboard).
- November 23rd – December 6th, 2023: Three women sued Diddy for physical abuse, drugging, and rape within a week and a half after settling Ventura’s lawsuit.
- December 7th, 2023: Singer-songwriter and activist Tiffany Red wrote a letter to Combs in Rolling Stone. She corroborated Ventura’s claims detailing events she witnessed at Ventura’s 29th birthday party in 2015. Lastly, Red accounts for how she tried to intervene and felt helpless.
- May 17th, 2024: A 2016 surveillance footage resurfaced depicting Diddy physically assaulting Cassie Ventura in a hotel hallway. The altercation resembled an allegation Ventura made in her lawsuit last November. According to LA Country District Attorney, George Gascon, “If the conduct depicted occurred in 2016, unfortunately, we would be unable to charge as the conduct would have occurred beyond the timeline where a crime of assault can be prosecuted.”
- September 17th, 2024: Police found 1,000 bottles of baby oil while searching Diddy’s New York residence. A month later, a lawsuit made by another Jane Doe alleged the baby oil, and other lubricants, were laced with GHB (Rohypnol) to drug women for his “freak offs” (E! Online).
JAIL PROCEDURES FOR THE MAINSTREAM
Expert Insight
Presently, Diddy is in jail waiting for his trial to start. Joseph E. Gunja, a Jails/Prisons/Correctional Facilities expert, has graciously opined on jail and prison protocol for high-profile inmates.
Before I delve into the procedures, a distinction between jails and prisons must be included. Jails are under local law enforcement agencies or correctional department supervision. They are for inmates who temporarily await trial and sentencing dates. Mr. Gunja notes that the staff overseeing the inmates receive annual 40-hour training related to their job description. State and federal entities oversee prisons. People go to prison for longer sentences, usually related to more serious crimes. Essentially, Diddy is temporarily in jail, and depending on the outcome of his trial, he may be sent to prison for a longer sentence.
According to Mr. Gunja, “Combs will not be treated any differently than other inmates.” The jail protocols apply to everyone regardless of social and economic status. Regarding visitation, Diddy is allowed to have social visitors, which are set by the staff. Alexandra Shapiro, his attorney of record, can visit as many times as necessary.
Aside from his current legal scandal, Diddy is constantly in the news and media given his celebrity status. Mr. Gunja states that jails “respond to the media inquiry with consultations with the regional Public Information Officer and Central Office Public Information Officer.” Lastly, some inmates may need constant supervision, as Diddy did last month when he was on suicide watch (NBC News). Mr. Gunja states that suicide watch must have the approval of a psychologist or other mental health professional.
CONCLUSION
Since Diddy’s legal scandal is ongoing, and the trial will not happen until next year, we will continue to discuss different aspects of his case with insight from various expert witnesses. A special thank you to Mr. Joseph E. Gunja for opining on jail procedures for high-profile inmates. Please stay tuned for the upcoming ‘Diddy Scandal’ blog post.