Diddy Depravity: How Hip-Hop’s Culture of Silence Helped Hide Its Biggest Bad Boy

Bonus Content: Enjoy This Premium Article on Us Diddy Depravity: How Hip-Hop’s Culture of Silence Helped Hide Its Biggest Bad Boy Sean Combs exemplified a hyper-masculine resolve, but did it enable a legacy of intimidation and aggression? By [Cortney Wills]( Sean "Diddy" Combs (Credit: Chris Smith for TheWrap/Getty Images) Now that Sean “Diddy” Combs has been charged with multiple felonies in an indictment that alleges rampant drug use, sex trafficking, prostitution and arson, some music industry insiders are bracing for what might come next: a reckoning in the world of hip-hop. Stories that stretch back decades about Diddy’s violent temper, his sexual proclivities and his mistreatment of women, are suddenly resurfacing across websites and social media platforms, with many commenting that he is finally being held accountable for behavior everyone seems to have known about for years. “What has been so confusing and frustrating is this idea that this is not a surprise,” music journalist and author Gerrick Kennedy told TheWrap. “There has been this sentiment for 20+ years now that [Diddy] is not someone you cross. There’s always been this acknowledgement that this is an unsavory actor.” This week, a New York federal grand jury handed down a 14-page indictment alleging Combs used his multiple businesses — ranging from record labels, clothing companies, liquor brands, his television network and media company — to execute shocking criminal activity including drugging and trafficking women and male sex workers at “freak off” parties. And everyone wants to know how the self-proclaimed “bad boy” could be so … bad? [World-class journalists will be joining TheGrill on October 8](. [Learn More]( With so many powerful people involved in Diddy’s rise, there are a lot of ideas swirling about who knew what and who might be implicated. “It’s like a really bad family tree,” one veteran entertainment journalist said, speaking under the condition of anonymity. “People will distance themselves. His team will bounce. People will resign. People who have been with him for decades will be called into question. People are mad that they’re being tied to him in any way.” Many interviewed by TheWrap said they were shocked to read the details in the federal indictment. But they acknowledged the culture of silence around Diddy’s behavior existed because of the access he offered in the music industry. “It’s an unspoken exchange,” one former music executive told TheWrap. “You were just happy to be in the room. All of a sudden, you realize the music videos and the rap lyrics are real and you have somehow managed to make it into the inner circle of trust. You’ve made it. You’re special enough to be trusted. You see someone doing drugs, see someone getting freaky, you look away and stay on the list for the next soirée.” Hip-hop has always applauded those who do whatever it takes to hustle hard and don’t take no for an answer. In that culture, Diddy exemplified a hyper-masculine resolve, even if it brought with it a legacy of intimidation and aggression. In some ways, insiders admit, that was celebrated. “A lot of people enjoyed having that idea of Puff,” Kennedy said, similar to how they thought about Suge Knight and Russell Simmons, two other controversial hip-hop moguls from the same era. Simmons was accused of sexual assault by multiple women in the #MeToo shakeout, and Knight is serving a 28-year sentence for running over and killing a rival in Compton. Kennedy added: “That is what hip-hop culture has been built off of. Hip-hop is built off these shrewd businessmen who move by any means necessary. That is something that has thrilled people. It has allowed them to paint these men in a particular way and then when we have moments where we have to hold them accountable, there’s all of this shock.” When women spoke up The veneer of an acceptable public image of Diddy was finally shattered in May, after a video leaked of the rap mogul beating his girlfriend Cassie Ventura in the hallway of a Los Angeles hotel in 2016. Security footage showing Diddy’s abuse of Cassie Ventura in 2016 (via CNN) Security footage from 2016 showing Diddy’s abuse of Cassie Ventura (via CNN) The previous November Ventura had filed a lawsuit that alleged horrific behavior. In her suit, she said she learned to “blindly” submit to avoid “vicious beating.” In an echo of the federal charges of orgies Diddy called “freak-offs,” Ventura alleged that Combs sex trafficked her, forcing her to get high or drunk and have sex with male prostitutes while Combs masturbated and filmed the interactions. She said she learned to “disassociate during these horrific encounters.” With the federal charges, many women — including a half-dozen [who have accused Diddy](in lawsuits of sexual assault, verbal abuse and beatings — are hoping for some vindication. “The purpose of justice is to provide an ending and allow us the space to create a new chapter,” Aubrey O’Day, a member of girl group Danity Kane who was mentored by Combs, [shared on her Instagram Story]( following Diddy’s indictment. “Women never get this. I feel validated. Today is a win for women all over the world, not just for me. “Things are finally changing,” the singer added. Longstanding rumors of the mogul’s explosive temper have also been framed in a new light, with the ancillary guilt of those who knew and remained silent. “The fact that there has been this pattern of behavior and the fact that he has been able to get away with it for so long is because you have this air of power,” the veteran journalist said. She added: “Some people say you can’t blame the people who were around him because if you were to do something or say something, who’s to say he won’t come after you with a gun? Or he wouldn’t attack you? Your silence is your own self preservation in some respects … Are we going to see the assistants who hired the sex workers or bought the baby oil tried as well?” Sean Combs and Russell Simmons in 2022. (Photo by Kevin Mazur/Getty Images) A rap sheet filled with aggression Despite his public persona as a family man, much of Combs’ career has been punctuated by moments of major turmoil. From his lyrics to his rap sheet to his bad boy reputation, Diddy has not hidden the fact that he’s capable of violence. In 1996, Combs was found guilty of “criminal mischief” for threatening a New York Post photographer with a gun. Three years later, he was charged with two felony counts after record executive Steve Stoute accused Combs and two bodyguards of beating him using a champagne bottle, a telephone and a chair over a disagreement about Nas’ “Hate Me Now” music video. In 2001, a jury acquitted him of shooting a gun inside of a New York City nightclub where a woman named Natania Reuben was shot in the face and of bribing his driver to take the fall for a second gun that was found in the vehicle he fled in with his then-girlfriend, Jennifer Lopez. In 2015, Combs was arrested for assault with a deadly weapon after allegedly hitting a UCLA football coach with a kettlebell for yelling at his son during practice. “That idea of ‘you don’t f–k with Puff’ was there because of the way he moved,” Kennedy explained. “It created this lore around him, and we all kind of celebrated that lore … We pick and choose how we want to see the unsavory parts. Culturally, we’re going to have to sit with that.” As far as how he conducted business, Diddy’s legendary temper has provided even more reasons for people to stay out of his crosshairs. In May, [Rolling Stone]( published a report in which dozens of former friends, colleagues and insiders detailed decades of Diddy’s violent tendencies. The publication chronicled aggressive incidents beginning from his time as a Howard University undergraduate and continuing throughout his rise to fame and fortune. The outlet said it interviewed hundreds of sources and noted many of them were still too scared of retribution to go on record. (Combs’ lawyers told the outlet at the time that “Mr. Combs cannot comment on settled litigation, will not comment on pending litigation, and cannot address every allegation picked up by the press from any source, no matter how unreliable.”) In July, Danyel Smith wrote a piece for [The New York Times](in which she recounted a harrowing experience she had in 1997 while working with Combs when she was editor-in-chief of Vibe. She denied his request for approval on the magazine’s cover, prompting him to tell her that he would see her “dead in the trunk of a car.” Stories about those kinds of threats and criminal activity were willingly overlooked or accepted by many of the people who are now wondering how they could have missed such a dangerous predator in their midst. Diddy came up in the 1990s and 2000s, when drug use was more normalized and there was no social media. “For me, it was really during ‘Making The Band’ that I saw that side of him,” the veteran journalist said. “To me, that was the first spark of feeling like something is wrong with him.” "It’s an unspoken exchange… You see someone doing drugs, see someone getting freaky, you look away and stay on the list for the next soirée." — A former music executive Hip-hop also emulated a kind of mob culture that reflected the federal racketeering charge Combs now faces. “Like the album covers and videos … it’s like he took it to the next level,” the veteran journalist continued. “There’s the sex trafficking and all of that, but it seems like the way the feds are going to stick it to him is through him using Combs Enterprises, using his businesses to racketeer. That’s what’s going to get him the jail time.” Lawsuits and raids Federal prosecutors brought criminal charges against Diddy only days after his former Diddy–Dirty Money bandmate Dawn Richard filed a lawsuit alleging the mogul assaulted, threatened, abused and imprisoned her over the course of several years. At his second bail hearing on Wednesday, prosecutors alleged that the third member of the trio, Kalenna Harper, released a statement that denied many of the allegations Richard made, only after Diddy or people close to him contacted her 128 times — 58 times through direct calls and texts from Diddy. That indicated his rumored history of intimidation was still in full effect and that he should stay behind bars until his trial, prosecutors argued. In Richard’s [55-page lawsuit](, the former Danity Kane member alleges she witnessed Combs brutally beat his girlfriend Ventura who launched her own [explosive lawsuit]( against the superstar last November. She alleged a history of violence, forced drug use, rape and that Diddy blew up Kid Cudi’s car in 2012 (a fact the rapper confirmed to [The New York Times.]() Combs vehemently denied the accusations but settled the lawsuit for an undisclosed amount a day later. [World-class journalists will be joining TheGrill on October 8](. [Learn More]( Dawn Richard and Sean Combs in 2010 (Getty Images) One week after that, an anonymous plaintiff in New York filed a lawsuit accusing Combs and singer Aaron Hall of rape, the same day as Joi Dickerson Neal filed a suit claiming Combs sexually assaulted her and secretly recorded the crime when she was a student in 1991. Several other similar suits have been filed since then, including one in December alleging the mogul gang raped a woman who was 17 at the time. By March, [Homeland Security had raided Combs’ mansions]( in Los Angeles and Miami in connection with a human trafficking investigation. In May, CNN released video footage showing Combs brutally assaulting Ventura in a hotel hallway, which seemed to clearly disprove his adamant claims that he was an innocent victim of her lies. And now people close to him and his businesses are starting to distance themselves. “People can separate the man from the company he built and what it has come to represent on its own merits,” one staffer at Revolt, the media and cable TV network co-founded by Combs, told TheWrap. “The people who work here don’t want to be associated with any of this and shouldn’t be.” Whether or not the public will suddenly stop sipping Cîroc or ban Bad Boy songs from their playlists remains to be seen. But given the way things tend to go in the music business, some are skeptical that the details divulged in the criminal indictment and lawsuits will do much to change the game in any meaningful way. “I don’t know if it will help protect women in the industry,” the veteran entertainment journalist said. “I hope these men will now realize that they’re in an environment where everything is being recorded, everything is on the internet and perhaps that will make them behave better.” Discover why entertainment executives and professionals rely on the WrapPRO platform daily for exclusive coverage, analysis and deeper reporting. [SUBSCRIBE NOW]( By subscribing to TheWrap newsletters, you acknowledge and consent to our Personal Contacts and Privacy Policy TheWrap | 2034 Armacost Ave. Los Angeles, CA 90025 [Preferences]( | [Unsubscribe](