Can't Stop, Won't Stop: The Legal Odyssey of Sean 'Diddy' Combs

Devisadaria Duchine-Khauli

17 May 2024

Updated 21 May 2024

Sean 'Puff Daddy, P. Diddy, Puffy, Diddy, and now Sean “Love" Combs' is no stranger to legal troubles, so to many the accusations against him do not come as a surprise. Speculations have persisted for some decades about Combs' involvement in abusing individuals. Additionally, there is video evidence showcasing his psychological abuse on Making the Band. On May 15, 2024, a video surfaced showing Combs physically abusing singer Cassie. Subsequently, on May 19, 2024, Combs attempted to apologize via Instagram, but it was poorly received.  Given Combs' history of documented violence, psychological abuse, and serious scrapes with the law, many question why it required the release of a video before Cassie's allegations were taken seriously. Presented below is a chronological overview of Combs' legal troubles and history of abuse.

Bad Boy for Life Timeline

In June 1996, Combs was found guilty of threatening a New York Post photographer.

On 15 April 1999, Combs accompanied by two men allegedly burst into Steve Stoute's office and assaulted him. The assault left Stoute with a broken arm and bruises. Combs was reportedly upset over the Hate Me Now video edits that showed Combs being strung up on a cross.

At the time, Stoute was president of Urban Music for Sony Music Entertainment, then President of the Urban Music division, executive vice president at Interscope Geffen A&M Records, and Mary J. Blige’s and Nas' manager. 

In June 1999, Stoute sued Combs which resulted in Combs paying him an out-of-court settlement. On 8 September 1999, Combs pled guilty to harassing Stoute and was sentenced to one day in an anger management class.

On 27 December 1999, Combs, Jennifer Lopez, his bodyguard Anthony “Wolf” Jones, and up-and-coming rapper Jamal Barrow, known as Shyne were at Club New York in Manhattan. Combs got into an argument with another of the club’s patrons, then shots were fired. Combs and Shyne were arrested for firearms violations and other crimes.

Combs was charged with criminal possession of a firearm and with bribery for asking his driver, Wardel Fenderson, to claim he owned the firearm used during the shooting. During the proceedings, Combs was represented by Johnnie Cochran and Benjamin Brafman.

On 16 March 2001, he was found not guilty on all charges. However, on 1 June 2001, Shyne was sentenced to ten years in prison for assault, criminal possession of a firearm, and reckless endangerment.  He served nearly nine of the ten years, and upon release was deported to his native Belize.

Wardel Fenderson filed a lawsuit against Combs claiming he suffered emotional damage as a result of the incident. The case was settled out of court in February 2004.

Making the Band

On 24 March 2000, Combs' television series, Making the Band aired on ABC, then moved to MTV during its second season. Making the Band was a reality television show that followed six contestants as they navigated the processes of recording an album while performing tasks to earn studio time for their project. The show gave viewers an inside look at some of the music industry's practices and Combs’ twisted psyche. 

Season 2, episode 1, is often referred to as the cheesecake episode and is the show’s most memorable and most viewed episode. During the episode, the six contestants were forced to sleep together in a small hotel suite. Upon waking up, they are told that they must walk from Manhattan to Brooklyn, to Junior’s restaurant to get a slice of cheesecake for Combs in exchange for studio time. This is one of the times the viewers observed Combs’ use of manipulation and psychological abuse. Ironically, Da Band never achieved the fame they were seeking. 

Throughout the show's run, Combs could frequently be seen verbally abusing the cast and crew, throwing tantrums, and making bizarre requests of the contestants, such as demanding they walk for over three hours to fetch him a slice of cheesecake, as mentioned earlier. In a skit for The Chappelle Show, Dave Chappelle and the cast from Making the Band's second season humorously reenacted and exaggerated some of Combs' tantrums and outlandish demands on the show. Chappelle's comedic portrayal of Combs sheds light on the absurdity of certain requests and the childlike behaviors exhibited by the music mogul. 

On 23 April 2023, Making the Band cast member Freddy P. sat in an interview with The Art of Dialogue, where he described an incident where Combs threatened his life. He said the threat led to him leaving the show and fearing for his safety. He said he took the threat seriously and contemplated killing Combs, but decided against it. In an interview with Complex, Freddy P. disclosed that the confrontation with Combs led to him considering suicide. However, he ultimately chose against taking his life, citing concern for his brother, as he didn't want his brother to discover him deceased.

On 15 April 2001, Combs was arrested in Miami Beach, Florida for driving under a suspended license.

In August 2007, Gerard Rechnitzer filed a lawsuit alleging Combs assaulted him outside Teddy's, a Hollywood nightclub. The lawsuit was settled out of court in March 2008.

Not safe, even amongst our own

On 11 May 2007, during an episode of Making the Band, choreographer, Laurieann Gibson alleged Combs threatened to hit her with a chair while Michael Bivins, of New Edition and Bell, Biv, DeVoe’s fame held her in place. Combs was heard telling employees, “Turn the cameras off.” During the clip, he grew angry as Gibson asked if she could interject. He told her no, threw her out, and told her how “psycho” he could get. The clip stopped. It resumed as Gibson screamed, “I’m not afraid of you,” and she was escorted from the building by six men. Combs could be heard telling her, "You were supposed to be a sista!" Gibson filed a police report that day.

He could have used sista to mean a Black woman or as a play sister. Regardless of how he employed the term "sista" in this context, its usage is problematic because it implies that she's expected to put up with abuse through "skinship" or through community "kinship."  

Black women are often discouraged from reporting crimes when Black men are the perpetrators. Tragically, if or when Black women do report crimes committed against them, they can encounter harassment from males and females within their communities. These women are seen as "snitches" and sometimes race betrayers, "for aiding in the incarceration of Black men."

In 2012, rapper Scott Mescudi, better known as Kid Cudi's car was blown up in his driveway after it was discovered by Combs that Ventura was dating him.  Kid Cudi was home entertaining friends when it happened. Combs was alleged to be connected with the crime but no charges were brought against him. 

In May 2017, Cindy Ruela, Combs' former chef, filed a sexual harassment and retaliation lawsuit against him in L.A. County Superior Court. In February 2019, the suit was settled out of court.

On 16 November 2023, Ventura filed her case against Combs under New York’s Adult Survivors Act, which is set to expire The case was settled the next day. 

Can't Stop Won't Stop

On 23 November 2023, Joi Dickerson-Neal (Seen in Finesse's & Synquis' music video, Straight From The Soul, in the car with Combs) filed a lawsuit against Combs alleging sexual assault and revenge porn. 

On 23 November 2023, Liza Gardner filed a lawsuit against Combs alleging she was 16 years old in 1990 when Combs and Aaron Hall of Guy and solo ventures, sexually assaulted her. 

On 6 December 2023, a lawsuit was filed in Manhattan district court by a woman who alleges that Combs and others gang raped her in 2003 when she was 17 years old. 

On 6 December 2023, he issued the following statement via Instagram:

On 26 February 2024, music producer Rodney Jones, known as Lil Rod filed a lawsuit in the Southern District of New York. The suit alleged that Combs drugged, sexually assaulted Jones, and forced him to engage in sex acts with prostitutes and others. Later, Cuba Gooding Jr. was added to the suit as a defendant. 

On 25 March 2024, Combs’ Los Angeles, Miami, and New York homes were raided simultaneously by the Department of Homeland Security using a Southern District of New York search warrant.

You Can Hate Me Now???

On 17 May 2024, CNN released the video they had obtained showing Combs beating Ventura, after his repeated denials. The video has validated some of Ventura's claims and left some to wonder if this is the incident Ventura described in her lawsuit. 

On 19 May 2024, Combs releases an "Apology" video, despite his repeated denials of wrongdoings.

It wasn't until the release of the hotel footage obtained by CNN that Combs admitted to that instance of abuse and attempted to apologize.

But was it an apology? The disturbing aspect of the apology lies in what he said and what he didn't say.

He began with an excuse. He said how difficult it was for him to reflect on the darkest times in his life. However, he removed himself from the abuse by saying, "It’s so difficult to reflect on the darkest times in your life, but sometimes you got to do that."

He never said what he was apologizing for. He never apologized to Ventura or even acknowledged the harm he caused her. The "apology" was filled with I's. In short, it was a narcissist's apology. Had it not been for the video, many believed there wouldn't have been an apology.

On 21 May 2024, former model, Crystal McKinney filed a lawsuit accusing Combs of sexually assaulting her by shoving her head into his crotch and forcing her to perform oral sex on him in 2003. 

On 21 May 2024, Ventura issued the following statement via Instagram regarding her abuse.

Combs' world seems to be collapsing around him. Due to the statute of limitations, it seems unlikely that Combs will be prosecuted for some of his crimes against Ventura or/and others. Hopefully, the alleged victims of his crimes will heal from their trauma, and perhaps
Combs can earnestly seek and receive help.