Diddy’s been a real Bad Boy - Timeline of controversies since Cassie’s assault video

SEAN "Diddy" Combs, the renowned hip-hop mogul, is currently embroiled in a series of serious legal challenges stemming from multiple allegations of sexual assault and misconduct.

This wave of lawsuits follows a high-profile case brought by his ex-girlfriend, Casandra Elizabeth Ventura, known as Cassie. In her lawsuit filed in November 2023, she detailed horrific allegations including rape, sex trafficking and physical violence.

Although the lawsuit was reportedly resolved just a day later through mutual agreement, it marked the beginning of a troubling trend for Diddy. Since then, he has faced at least twelve additional lawsuits from various individuals accusing him of similar offenses, including sexual assault and drugging.

The situation escalated significantly when Diddy was arrested on Sept 16 following federal raids on his properties in Los Angeles and Miami as part of an ongoing sex trafficking investigation. He was charged with racketeering and sex trafficking and remains in federal custody after bail was denied

Among the latest allegations is a lawsuit filed by Thalia Graves, who claims that Diddy and his former bodyguard raped her in 2001 after drugging her. Graves alleges that they recorded the assault and distributed the footage as pornography. In her emotional press conference, she expressed relief at Combs' arrest but emphasised that it is only a temporary respite from the trauma she endured.

Diddy has publicly denied all allegations against him, stating that he is being targeted by individuals seeking financial gain. "Enough is enough," he declared on December 6, 2023. "I will fight for my name, my family, and for the truth". As more individuals come forward with accusations against him, the impact on his career and reputation continues to unfold, with several companies reportedly severing ties with him amid these serious allegations

The unfolding legal battles have not only affected Diddy's personal life but are also reshaping perceptions of his legacy within the entertainment industry. Here's a quick recap of what has been reported so far:

Nov 16, 2023

Two months after winning the Global Icon Award at the 2023 MTV Video Music Awards, ex-girlfriend Cassie accused him of rape, sex trafficking, and domestic violence in a lawsuit.

In her complaint, she attempted to end the relationship multiple times, all ending with alleged Diddy forcing her not to, where in Sept 2018 over dinner, Diddy forced his way into her home and raped her when she already said no and tried to push him away. Cassie claimed that she endured "horrific abuse" throughout their relationship, stating that Diddy would sometimes become "uncontrollably enraged" and "violently assault" her.

In her lawsuit, she also made another claim that Diddy blew up Kid Cudi's car in 2012 after discovering the rapper had a "romantic interest" in her.

Cassie's lawyers further alleged that she suffered "over a decade of violent behaviour and troubling demands," which included frequent physical abuse and being coerced into "sexual acts with male sex workers."

According to Cosmopolitan, Diddy's lawyer, Ben Brafman dismissed the claims as "offensive and outrageous," firmly stating that Diddy "vehemently denies these allegations." He also revealed that Cassie had demanded $30 million, threatening to release a damaging book about their relationship, which Brafman characterised as "blatant blackmail" and was rejected outright.

In response, Cassie's attorney, Douglas Wigdor, issued a statement asserting that Diddy had offered her an eight-figure sum to silence her and prevent the lawsuit.

She rejected the offer, choosing instead to "give a voice to all women who suffer in silence," where Wigdor praised Ventura's "bravery" for her decision. The lawsuit reached a settlement for an undisclosed amount in less than 24 hours, where mutual satisfaction was reached.

“I have chosen to settle this matter on terms where I have some control,” Cassie stated through Wigdor. “I want to express my gratitude to my family, fans, and legal team for their unwavering support.”

Diddy echoed the sentiment, saying, “We’ve both agreed to resolve this matter amicably. I wish Cassie and her family the very best. Love.”

Brafman clarified his client’s position, telling PEOPLE, “To be clear, settling a lawsuit in 2023 is not an admission of guilt. Mr Combs' decision to settle does not contradict his complete denial of the allegations. He’s pleased with the mutual resolution and extends his best wishes to Ms Ventura.”

Nov 23, 2023

Diddy's sexual assault allegations began ratcheting up. He faced two additional sexual assault lawsuits, one filed by an anonymous plaintiff and the other by a woman named Joi Dickerson-Neal.

The former accused him of assaulting and beating her, while Dickerson-Neal alleged that he drugged and sexually assaulted her when she was a college student in 1991. She also claimed that Diddy had recorded the assault and allegedly shared the footage with others in the music industry.

Nov 28, 2023

Diddy stepped down as the black-owned media company Revolt's chairman due to the three lawsuits that had been made, where he helped launch Revolt back in 2013.

“While Mr Combs has previously had no operational or day-to-day role in the business, this decision helps ensure that Revolt remains steadfastly focused on our mission to create meaningful content for the culture and amplify the voices of all Black people throughout this country and the African diaspora,” the company reportedly said in their statement.

“Our focus has always been one that reflects our commitment to the collective journey of Revolt—one that is not driven by the individual but by the shared efforts and values of our entire team on behalf of advancing, elevating, and championing our culture, and that continues,' they added.

Then, Curtis “50 Cent” Jackson, who is known to have beef with Diddy shown through several online interactions, had consistently mocked him during his recent trials, going so far as to offer to buy Revolt after news surfaced of Diddy stepping down.

“I’ll buy it from you, playboy, for a bargain since Cadillac and AT&T are likely to withdraw,” he commented. “I’ll give you some cash for it now! Sell it to me, and maybe we can be friends... I’m serious, give me a call.”

Dec 6, 2023

Diddy refuted all allegations after a fourth lawsuit was filed. A Jane Doe accused former Bad Boy Records president Harve Pierre and another person of sexual misconduct in 2003 when she was just 17 years old. Diddy released a statement on social media, denying all the claims against him he claimed were trying to destroy his reputation.

Dec 10, 2023

Brands began cutting ties with his e-commerce company, Empower Global, amid the escalating sexual misconduct allegations against the music mogul, as reported by the UK Cosmopolitan.

“While this decision was difficult due to the respect we once had for Mr Combs as a leader in business and entertainment, it was clearly the right choice,” said Lenard Grier, co-founder of No One Clothiers, regarding their decision to withdraw from the partnership. "Our brand is built on the principle that every individual deserves respect, regardless of gender, ethnicity, age, or other factors. The allegations against Mr Combs directly contradict these values, leading us to feel a moral obligation to terminate our relationship."

Other companies that ended their partnerships with Empower also expressed similar sentiments to the magazine.

Dec 13, 2023

A Hulu series focusing on Diddy's family was cancelled in December. Named Diddy 7, it was still in the early development phase and had not entered production. The project was slated to be produced by James Corden's company, Fulwell 73, for Hulu.

Feb 26, 2024

Music producer Rodney "Lil Rod" Jones Jr had filed a lawsuit against Diddy, alleging sexual misconduct, assault, and harassment. Lil Rod, who worked on The Love Album: Off the Grid 2023, claims that Diddy groped him and attempted to groom him into engaging in sexual acts with him and other members of his team.

In the complaint, Lil Rod also accused Diddy of "forcing" him to "solicit sex workers," some of whom were reportedly underage, and to have them perform sexual acts for Diddy's pleasure. He recounted an incident in February 2023 when he woke up naked, dizzy, and confused in Diddy's Miami home, alongside the Bad Boy artist and two sex workers.

Lik Rod suspected he was drugged.

Additionally, the producer was suing Diddy, UMG, Motown, Love Records, and Chalice Recording Studio for allegedly providing "inadequate or negligent security" that night.

Diddy's attorney, Shawn Holley, dismissed Lil Rod's claims, stating that the producer was merely seeking an "undeserved payday." She said: “We have overwhelming, indisputable evidence that his allegations are completely false...We will contest these outrageous claims in court and take appropriate action against those who make them.”

March 25, 2024

Federal agents conducted raids at his homes in Los Angeles and Miami, with the Department of Homeland Security Investigations (HSI) New York executing search warrants. These raids were part of an ongoing federal investigation into sex trafficking, led by prosecutors from the Southern District of New York.

“HSI New York carried out law enforcement activities as part of an ongoing investigation, with support from HSI Los Angeles, HSI Miami, and local law enforcement agencies. We will provide additional information as it becomes available,” the Department of Homeland Security stated.

An alleged Diddy's associate was arrested on drug charges in Miami. Brendan Paul, a 25-year-old accused of being a drug mule for Diddy in a recent lawsuit, was detained at Opa-Locka Airport on March 25, coinciding with the raids on Diddy’s residences. He faced charges of possession of cocaine and marijuana.

March 26, 2024

Diddy reportedly sold his stake in Revolt TV after resigning as chairman in November amid sexual assault allegations. He transferred his remaining shares to an anonymous buyer, with the company still being reported as black-owned. The financial details of the sale were not disclosed.

On the same day, his attorney criticised the raids, calling them a "witch hunt."

"There was a gross overuse of military-level force as search warrants were executed at Mr Combs’ residences,” Dyer said in a statement to Billboard. “There’s no justification for the excessive display of force and the hostility shown by authorities, as well as the treatment of his children and employees. Mr Combs was never detained; he spoke to and cooperated with the authorities.”

Dyer also noted that Diddy and his family have not been arrested and are free to travel as they choose, even after the two raids.

May 10, 2024

Diddy sought to have a rape claim dismissed. He requested that a federal judge reject the lawsuit filed in December 2023, asserting that the allegations that he and two co-defendants raped a 17 year-old girl in 2003 were false and outrageous.

He also contended that the lawsuit was filed too late.

“Mr Combs and his companies categorically deny the plaintiff’s decades-old narrative, which has inflicted severe harm on their reputations and business standing without any evidence presented. The plaintiff is unable to specify the date or time of the alleged incident, yet can somehow recall other scandalous details, despite claiming to have been incapacitated,” the filing stated.

The filing further requested that the case be “dismissed now, with prejudice” to avoid additional “reputational damage” and to conserve judicial resources.

May 17, 2024

CNN obtained a 2016 surveillance video showing Diddy allegedly assaulting Cassie during a hotel stay. In the footage, Diddy, clad only in a white towel, is seen pushing her to the ground near an elevator, kicking her multiple times while she is on the floor, and dragging her down a hallway.

Later, he appears to grab an object from a table and throw it at her before walking away, only to turn back just as an elevator door opens.

The incident, aligning with the assault allegation Cassie made against Diddy in her settled lawsuit, triggered Wigdor to make a statement: “The gut-wrenching video has further confirmed Mr Combs' disturbing and predatory behaviour. Words cannot express the courage Ms Ventura has shown in coming forward.”

On the same day the video emerged, Cassie's husband model Alex Fine shared a screenshot of a statement he had written, which began, “Men who hit women aren’t men. Men who enable and protect those individuals aren’t men. Violence against women shouldn’t be inevitable; check your brothers, friends, and family. To all the women and children, I’m sorry you live in a world where you’re not protected and don’t feel equal.”

Fine concluded his post by stating that while he wrote these words some time ago, their message remains relevant.

On the same day, the office of Los Angeles County District Attorney George Gascón released a statement on Instagram addressing why the hotel video, while “disturbing,” would not lead to criminal charges against Combs.

They noted, “The images are extremely difficult to watch. If the conduct occurred in 2016, we unfortunately cannot charge, as it falls outside the statute of limitations for prosecuting assault.”

Two days after the video’s release and following months of denying various assault allegations, Diddy posted a 70-second self-recorded apology on Instagram.

In the clip, he reflected on his “darkest times” and admitted, “I hit rock bottom. I make no excuses. My behaviour in that video is inexcusable. I take full responsibility. I’m disgusted then and now.”

Following the release of the video, New York City mayor Eric Adams mentioned in an interview that the city was considering revoking the Key to the City that had been given to Diddy in September 2023.

May 21, 2024

Model Crystal McKinney filed a lawsuit against Diddy accusing him of sexual assault. She alleged that in 2003, he forced her to perform oral sex on him in a bathroom at a New York City recording studio.

McKinney also claimed she was provided with alcohol and marijuana, which she later suspected were laced with narcotics or other intoxicating substances. After the alleged assault, she said she "awakened in shock" in a taxi, leaving the scene.

Named as co-defendants in the lawsuit were Diddy's label, Bad Boy Records, its parent company, Universal Music Group, and his clothing brand, Sean John Clothing.

McKinney said these companies "enabled" the alleged assault by continuing to employ Diddy n a position of power, despite allegedly being aware or should have been aware of the risk he posed for sexual assault.

May 21, 2024

There was a viral poster for the fake documentary 'Diddy Do It,' created by Kode Abdo as a parody last March.This generated buzz alongside rapper 50 Cent teasing his legitimate documentary about Diddy, which focuses on allegations of misconduct against Combs and later won the bid to be officially published by Netflix. This was confirmed by 50 cent himself on his X platform.

July 12, 2024

Amid Diddy's allegations, he is also confronted with a diss track "Fuel" by rapper Eminem featuring JID as part of Eminem's album The Death of Slim Shady.

The lyrics appears to be a reference to Diddy's alleged involvement in the murders of Tupac Shakur and The Notorious B.I.G. and also indirectly labelling the mogul a rapist.

"Wait, he didn't just spell the word 'rapper' and leave out a P, did he? (Yep)

R.I.P., rest in peace, Biggie

And Pac, both of y'all should be living (Yep)

But I ain't tryna beef with him (Nope)

'Cause he might put a hit on me like, 'Keefe D, get him'

And that's the only way you're gonna be killing me (Nah)"

Eminem also said "Got so many S-As (S-As), S-As." in the lyrics, indirectly hinting Diddy's many sexual assaults cases.

Sept 6, 2024

The death of Diddy's ex-wife, Kimberly Anita Porter has been the subject of public scrutiny, with some, including former President Donald Trump Jr, suggesting that she lived in fear of Diddy.

Recently, a diary purportedly written by Porter has surfaced, intensifying these allegations. Published by Chris Todd under the pseudonym Jamal T. Milwood, the 60-page diary details claims of emotional and physical abuse, including accounts of death threats and other troubling domestic experiences.

“This was supposedly for Kim Porter from the grave, to come forward and tell her story,” Todd remarked regarding the publication of the diary.

Porter died in November 2018 from pneumonia.

Diddy's mugshot and arrest on Sept 16, 2024.

Sept 16, 2024

Diddy was arrested in Manhattan following a grand jury indictment, where authorities reportedly found over 1,000 bottles of baby oil and lubricant. The raid was part of an investigation into allegations of sexual abuse and trafficking.

Alongside the baby oil, law enforcement also seized firearms, including AR-15 rifles with defaced serial numbers

One of Diddy's lawyer, Marc Agnifilo confirmed the arrest to the public.

Speculation arose that the baby oil might have been used as a lubricant during alleged sex parties referred to as "freak offs," which are described in the indictment as orchestrated sexual events involving multiple participants.

Agnifilo acknowledged that while there was a lot of baby oil, he questioned its relevance to the charges against Diddy.

"We are disappointed by the decision to pursue what we believe is an unjust prosecution of Mr Combs by the US Attorney’s Office," Agnifilo stated, describing his client as an imperfect person but not a criminal.

Sept 17, 2024

Federal prosecutors unsealed the indictment the day after his arrest, accusing him of leading a racketeering conspiracy involving sex trafficking, forced labour, bribery, and other offences.

According to PEOPLE, "For decades, Sean Combs... abused, threatened, and coerced women and others around him to satisfy his sexual desires, protect his reputation, and conceal his actions," one of the documents said.

It further detailed that Diddy utilised the employees, resources, and influence of his extensive business empire to do so. Shortly after the indictment, a federal judge denied him bail during a hearing. Diddy, who pleaded not guilty to charges including sex trafficking and racketeering, would remain in custody until his trial.

On Sept 18, he was again denied bail after a federal judge ruled that he posed a flight risk and could intimidate witnesses if released. During a Manhattan federal court hearing, Diddy's lawyers renewed their request for him to await trial under house arrest at his Miami mansion, offering a $50 million bond and agreeing to strict conditions.

However, Judge Andrew L. Carter ruled that Diddy must remain in a Brooklyn federal prison until the trial, citing concerns that he could endanger others or interfere with the government's case. Following the arrest, several allegations of associations with Diddy and enabling his behaviour surfaced, that affected celebrities such as Justin Bieber.

Videos of Bieber interacting with Diddy resurface recently and been put under scrutiny, including a video showing Diddy checking him for a "wire," in fear of him wanting to expose him in order to avoid further controversy for their association.

However, these remain indirect allegations, while Bieber has remained silent on the Diddy arrest issue since he had just conceived a child with his beloved wife, Hailey Bieber and wanted to focus on his personal life.