Sean 'Diddy' Combs’ History of Controversy, Legal Trouble

Sean “Diddy” Combs has spent most of his career surrounded by controversy and scandal. However, none has been as serious as the legal trouble he now finds himself in: On Sept. 16, the rapper/producer was arrested on charges of racketeering, conspiracy and sex trafficking. The following day, he pleaded not guilty and was denied bail.

This isn’t Combs’ first run in with the law, but it could possibly lead to the worst consequences he’s ever had to face. As we monitor this situation, we’re examining Diddy’s past history of legal issues and controversies.

In the mid ‘90s, rap music was dominated by the ongoing feud between East Coast and West Coast artists; specifically, Bad Boy and Death Row. Insults and diss tracks went back and forth as the tension rose to a dangerous level. Unfortunately, it reached a tragic peak with the murders of Tupac Shakur and Notorious B.I.G., two of the most influential artists in music history. Diddy has never been arrested, charged or credibly connected to either attack, but that hasn’t stopped conspiracy theories from continuing to suggest he was somehow involved.

The controversial video for his song with Nas, “Hate Me Now,” features a scene of the two men crucified on cross with crowns of thorns. Diddy decided the scene was blasphemous and wanted it cut from the video, but the unedited version aired on MTV. In response, the Harlem native went to the office of then-president of Interscope Records Steve Stoute and assaulted him with “a chair, a telephone and a champagne bottle.” He pled guilty to a reduced charge and was sentenced to one day of anger management.

While attending a New York nightclub with then girlfriend Jennifer Lopez, a shooting at the club caused chaos. Later that night, the couple and two other passengers were stopped by police and ended up “charged with criminal possession of a weapon and possession of stolen property.” J.Lo, whose movie career was just taking off, found herself connected to Combs’ highly-publicized criminal trial and the couple eventually broke up. Puff Daddy was found not guilty and changed his name to P. Diddy.

In 2003, a report revealed that Sean John workers in a Honduras factory were essentially dealing with sweatshop conditions. Sean John executives, including Combs, said they didn’t know about the problems but would work to fix them.

When P. Diddy became Diddy he forgot to ask around. As it turns out, Richard “Diddy” Dearlove, a producer in the United Kingdom, was already using the name. After a legal battle, there was a “£100,000 settlement in September 2006” and he must remain P. Diddy in the UK.

Detroit talk show host Rogelio Mills alleged that Diddy and his entourage assaulted him in 1999 after he asked about the producer’s role in Biggie’s death. The jury ruled in favor of Combs, a decision upheld on appeal.

The LOX got into it with Diddy about his mistreatment of artists and refusal to return their publishing rights. This moment went down on New York’s Hot 97, cementing the claims that he didn’t fairly compensate Bad Boy artists. Even though they eventually settled the dispute, the reputation for being a predatory record executive follows Diddy to this day.

A nightclub promoter sued the “Coming Home” rapper for $4 million, claiming Diddy had his bodyguard “forcibly remove” the promoter. He alleged he was “punched, kicked and chased around the club.”

In light of Cassie’s allegations, this is particularly disturbing. In November 2012, the two rappers reportedly got into a fight over the singer in a Hollywood club. Rumors say they “exchanged some heated words to the point where the entire club was watching – creating a huge scene.”

After he thought a football coach at UCLA was too hard on his son Justin, Combs allegedly assaulted the man with a kettlebell leading to the Bad Boy founder’s arrest for assault with a deadly weapon. In the end, the Los Angeles District Attorney’s Office didn’t pursue felony assault charges.

A woman who worked as a former private chef for the music producer filed a sexual harassment lawsuit alleging that she was forced to serve him “post-sex meals while he was naked.” She also accused him of not paying her for long overtime hours. In 2019, the suit was settled though no details were released.

At Clive Davis’ 2021 Pre-GRAMMY Gala, Diddy decided to call out the Recording Academy for its lack of acknowledgement and appreciation for rap and R&B categories. He portrayed himself as just another artist trying to represent for his people, but former Bad Boy star Ma$e took exception with his speech. He responded on Instagram, writing, “Your past business practices knowingly has continued purposely starved your artist and been extremely unfair to the very same artist that helped u obtain that Icon Award on the iconic Badboy label.” Their long standing beef recently made news again when Combs declared he was returning publishing rights to former Bad Boy artists, producers and songwriters. Some of those former artists have questioned his motives for this “act of kindness.”

After building the extremely successful Ciroc vodka and DeLeon tequila brands, Diddy accused distributor Diageo of racism alleging they didn’t offer the same resources to Black-owned brands that they did other brands. In response, Diageo ended its business partnership with Combs. As this dispute dragged on, Diddy has used social media to throw shade by complimenting other spirit brands.

Cassie Ventura shocked the world when she filed a bombshell lawsuit accusing the mogul of “years of physical abuse,” rape, sexual assault and sexual battery. The details behind their 11-year relationship are extremely disturbing. Combs’ lawyers claim the lawsuit is about money, but these may be the allegations the billionaire can’t make go away.

A day after Cassie filed her lawsuit, Combs settled with his ex. Details of the suit were not disclosed, but Cassie said in a statement, “I have decided to resolve this matter amicably on terms that I have some level of control. I want to thank my family, fans and lawyers for their unwavering support.”

“We have decided to resolve this matter amicably. I wish Cassie and her family all the best,” Combs said in a statement.

Cassie’s allegations of rape, sexual assault and domestic violence opened a door for other women to accuse the rapper/producer of sexual assault. As of this writing, three other women have alleged that Diddy sexually assaulted them, one of whom alleges that in 2003 she was “trafficked and gang-raped by Diddy, Harve [Pierre, former president of Bad Boy], and an unidentified third man” when she was 17.

Combs responded to the allegations in a statement on Instagram:

“Enough is enough. For the last couple of weeks, I have sat silently and watched people try to assassinate my character, destroy my reputation and my legacy. Sickening allegations have been made against me by individuals looking for a quick pay day. Let me be absolutely clear: I did not do any of the awful things being alleged. I will fight for my name, my family and for the truth. Sean Diddy Combs.”

In February 2024, Rodney “Lil Rod” Jones came forth with disturbing allegations against Combs. Jones, who worked on “The Love Album: Off the Grid,” stated that he lived and traveled with Combs from September 2022 to November 2023. Jones asserted that the mogul forced him to obtain sex workers and pressured him to engage in unwanted sexual acts with them.

He also said Combs assaulted him with “constant unsolicited and unauthorized groping and touching of his anus.” Jones also accused other high profile celebrities, which are believed to be Meek Mill and Usher, of engaging in sexual activity with men. He also stated Combs and his son, Justin, were responsible for shooting one of Justin’s friends at Chalice Recording Studio in Los Angeles on Sept. 12, 2022.

According to People, on Monday, March 25, Jones amended his complaint to include Oscar winner Cuba Gooding Jr. as a defendant.

Jones alleges that in January 2023, while on a yacht rented by Combs in the US Virgin Islands, the “Jerry Maguire” star, “began touching, groping, and fondling [his] legs, his upper inner thighs near his groin, the small of his back near his buttocks, and his shoulders.”

The complaint states Jones was “extremely uncomfortable,” but even after he rejected the actor, Gooding “did not stop until Mr. Jones forcibly pushed him away.”

Following a string of sexual assault lawsuits, he became the subject of a federal sex trafficking investigation, which led to his homes in Miami and LA being raided by the Department of Homeland Security.

According to Rolling Stone, on March 25, Brendan Paul, a 25-year-old man who “accused in a recent lawsuit of being Sean Combs’ drug ‘mule,’” was arrested at a Miami airport for cocaine and marijuan possession. The arrest happened around the same time Diddy’s homes in Miami and LA were being raided by Homeland Security.

Amid his recent legal troubles, Combs quietly sold his shares in the media company. According to TMZ, the buyer and amount are both undisclosed, but it’s still Black-owned.

The world was shocked when CNN obtained surveillance footage from 2016, which featured Combs assaulting his then-girlfriend Cassie. In the video, she is seen trying to leave their room in a Century City hotel, with Diddy following her into the hallway where he drags, kicks and shoves her. The outrage at Diddy, his allies and the hotel was loud and relentless. The rapper issued an apology, but the damage was done.

Around a week after the video was released, Cassie took to Instagram to thank everyone for their support, while also encouraging people to “open your heart to believing victims the first time.”

“The outpouring of love has created a place for my younger self to settle and feel safe now, but this is only the beginning,” she wrote.

Shortly after the surveillance footage made global headlines, Diddy released an apology video on Instagram where he said in part, “I was fucked up. I hit rock bottom. But I make no excuses... I’ve been going to therapy, and going to rehab. I had to ask God for his mercy and grace. I’m so sorry. But I’m committed to be a better man each and every day. I’m not asking for forgiveness. I’m truly sorry.”

The apology didn’t go over well on the internet, with many social media users calling it insincere and disingenuous, pointing to his previous denial stating he didn’t do the “awful things” he’s accused of.

In a new report from The Daily Beast, several former employees from Diddy’s companies—lifestyle brand Sean Jean and advertising company Blue Flame—have come out to accuse the hip-hop mogul of creative a toxic work environment, allegedly workplace abuse and more.

In September, the New York native found himself in the most serious legal trouble of his life when he was arrested on charges of racketeering, conspiracy and sex trafficking. He pleaded not guilty and was initially denied bail, with federal prosecutors stating that he was “too dangerous” to be released. His attorneys appealed the decision, citing the dangerous conditions at the Metropolitan Detention Center in Brooklyn.