Diddy’s (Alleged) Dirty Deeds: Sinister Stories & Scandals Through The Years

A Hip Hop empire has fallen now that Sean “Diddy” Combs has been taken into federal custody. The media mogul rose through the industry’s ranks to become one of the most successful Rap moguls to date, but his career has been fraught with controversy since its inception. Diddy has reigned over his Hip Hop kingdom with precision, floating through each of his monikers at various stages of his development. After helping to put Uptown Records on the map, Combs founded Bad Boy Records, an iconic label that gave us The Notorious B.I.G., Faith Evans, Total, The LOX, Craig Mack, 112, Shyne, Cassie, Mase, and many more. During its heyday, there were only a few labels to contend with the megahits rolling out of Bad Boys’ studios, but these days, Diddy’s alleged dirty deeds have placed him in a spotlight that the hitmaker would have rather avoided.

As Diddy faces an onslaught of lawsuits alleging violence and sexual abuse, he’s also looking at the possibility of spending the remainder of his life in prison. Federal authorities reportedly arrested Combs in New York City last week after being charged with racketeering and sex trafficking. Although his legal team hoped he could await his trial in the comforts of his lavish estate, a judge ordered Diddy to remain behind bars until the launch of his trial. This shocking decision, along with the reports of what authorities located in Diddy’s home during their raid, has taken over timelines. Even the mega-mogul’s peers have come forward, some to defend his character, while others share wild, alleged “Diddy Party” stories of their own.

It was Cassie Ventura’s explosive lawsuit against her former lover last year that seemed to propel this current investigation. We’ll get more into that as we go on, but Combs settled that suit out of court just 24 hours after Ventura filed her paperwork. However, hers wasn’t the first allegation of abuse—for over a decade, stories have haunted Puff from the courtroom to the streets. These accusations have surfaced from Wendy Williams to Combs’ former employees to Al. B Sure defending the late Kim Porter to models who have retained their own attorneys. Meanwhile, the internet is walking down memory lane as it revisits some of Diddy’s most controversial moments. The list of rumors and allegations is enough for a miniseries, but we’re gathering just a few of the most discussed from the life of Sean Combs that have kept him in infamy.

In March 1997, Hip Hop suffered a great loss when Christopher Wallace, better known as The Notorious B.I.G. or Biggie Smalls, was fatally gunned down in Los Angeles. For decades, speculation has circulated in the industry regarding Biggie’s death, and some even named Combs in rumors of a plot. Then, Rolling Stone released an exposé that shook the foundation of the case—they purported Wallace wanted out of his Bad Boy contract and was working on his exit from the label. The publication further stated that Biggie turned to his legal team to gain rights to his publishing, and there was a covert battle between Puff and Big about the concerns.

Upon news of Biggie’s death, RS claimed that Combs capitalized on the tragedy for financial gain. Rolling Stone approached Bad Boy for a magazine cover just months after Big’s murder. However, Kirk Burrowes, who co-founded the label and was acting as president of the company at the time, said that Diddy didn’t want Big on the cover. Instead, Combs graced the August 1997 issue, with Burrowes alleging that Diddy wanted to promote his debut album, No Way Out. Meanwhile, Biggie’s murder officially remains unsolved, although there is still gossip involving Combs, Suge Knight, and a host of characters.

Mega music executive Steve Stoute also had his name tied up in Diddy’s madness, albeit back in 1998. At that time, Stoute was acting as Nas’ manager, and it was then that he reportedly had a heated altercation with Combs. According to The Los Angeles Times, Stoute recalled he and Diddy exchanging words on the music video set of “Hate Me Now.” As the story goes, the idea for the video was for Combs to be depicted as a crucified Christ. Diddy wanted the scene axed, but somehow, it wasn’t removed. This reportedly angered Combs, who, Stoute said, showed up at his office and went after him with a champagne bottle. Stoute alleged that during the attack, his jaw and arm were broken.

The altercation resulted in Diddy receiving assault charges, but he denied any bones were damaged. Combs would later speak with MTV about the incident, claiming he apologized to Stoute. He also stated he “disappointed myself” as well as the “Hip Hop community.” Combs added, “Because everything I do, I’m trying to be a team player in taking Hip Hop to the next level.” Later, Diddy pleaded guilty to harassment and was ordered to take an anger management course.

This story has resurfaced after famed journalist Touré revisited the tale in a TikTok video. According to the clip, Danyel Smith was an editor at Vibe magazine in 1995 when Diddy graced the cover. She actually previously shared this story with The New York Times, claiming that days following the cover photo shoot, Combs reached out demanding to see the images before they were published. Smith denied the request because it wasn’t Vibe‘s protocol—along with most magazines. After being rejected, Smith stated she heard through the grapevine that Combs planned to visit Vibe‘s offices in an effort to force her hand. Days later, Smith alleged that Diddy showed up irate, requesting to see her immediately while searching for her. Smith remarked she was doing her best to avoid the upset mogul and managed to sneak out of the back door and hail a cab home.

This wasn’t the saga’s end; Puff allegedly called again the next day, wanting to see the pictures. Smith once again said no, and it was then that she claimed he threatened to “see you dead in the trunk of a car.” Combs is also accused of telling her he knew her exact location at that moment, and Smith said she wasn’t taking any chances. She contacted her attorney, resulting in the mega-producer issuing an apology. Again, one would think this is the conclusion of a wild story, but according to Smith, within days, there was another controversy. She stated that when she returned to work, the servers that held all the information for Diddy’s Vibe issue were no longer there. They were purportedly stolen, but despite the setback, the issue was published.

Probably one of the most significant controversies in Combs’ career is tied to Moses “Shyne” Barrow. Shyne was an emerging artist under the Bad Boy umbrella, with his deep, captivating cadence that caught the attention of both fans and the industry. However, a night out at the club in December 1999 would derail Shyne’s career after it turned into a shooting that injured three people. Now, what occurred that evening has been under speculation for years. What is known is there was an altercation that escalated into someone pulling out a firearm—and Shyne was accused of having his finger on the trigger.

Shyne and Diddy faced charges related to the shooting, but the latter was acquitted despite authorities claiming they found weapons in his vehicle. Yet, Shyne wasn’t so lucky and was sentenced to 10 years in prison. Since then, he has turned his life around after returning to Belize. Now an activist and politician, Shyne has left his Hip Hop life behind him. However, he has reunited with Diddy on stage at least twice since 2022. After learning of Combs’ recent arrest, Shyne spoke with reporters to share his thoughts. He said this wasn’t someone “who I vacationed with and someone who I enjoyed this great, intimate relationship of brotherhood. This is someone who destroyed my life.”

Over the years, several Bad Boy artists have come forward with complaints over their former label head not budging on giving them their publishing rights. Several of the Golden Era of Hip Hop hitmakers like Mase, members of 112 and Danity Kane, and others reportedly petitioned Combs for control of their publishing, to no avail. Pertaining to Mase, the Harlem World rapper took his grievances to the internet, publicly calling out his former friend. Following much controversy and scandal, Diddy decided to give his former artists their publishing rights in 2023. The move was praised by those who have complained throughout the years, aside from former Danity Kane singer Aubrey O’Day. The Making the Band star has long spoken out against Combs, even stating that in order to receive her publishing, she was allegedly told she needed to agree to no longer speak critically of Puff. In light of his federal charges, O’Day has celebrated his arrest.

Two weeks ago, Combs was hit with another lawsuit, this time from former Danity Kane singer Dawn Richard. Years ago, during an interview with Hot97, Richard seemingly praised Diddy and spoke about being loyal to him for helping develop her career on Making the Band. However, there were rumors of misdealings and ill feelings behind the scenes, and her recent lawsuit was yet another that stopped the industry in its tracks.

According to Richard’s court documents, she has accused Combs of physical violence and intimidation. She specifically named alleged incidents, including one involving Cassie Ventura. Richard stated she was at a dinner with Jimmy Iovine, Ne-Yo, and Usher, and it was there that Diddy allegedly punched Cassie in front of the guests, and no one moved or came to the singer’s aid. Richard also stated that she witnessed Combs threaten Ventura, choke her, and drag her upstairs. Richard also claimed Diddy locked her in a car for hours, “manipulated her” by threatening her career, and tried to convince her that women in the industry would have to face “abuse and exploitation” to be successful.

Further, Richard’s suit also included mentions of Diddy’s infamous parties, or as the federal authorities have called them, “freak offs.” The singer stated that she witnessed these events with “passed out” women who were alleged victims to Combs and his friends, who “performed sexual acts on them.” Moreover, Richard said she was violated when Combs allegedly grabbed her “bare buttocks” while she was in a changing room, even attempting to “touch her breasts.” When she continued to deny his advances, Richard claimed Diddy stifled her career. The lawsuit is ongoing.

Last year, Cassie filed a lawsuit against Diddy, unraveling a bevy of allegations of abuse throughout their 11-year relationship. These accusations included rape, physical violence, intimidation, manipulation, and forcing her to engage in sexual acts with male escorts. Additionally, there was a story about an artist whose car was blown up because Diddy supposedly believed he and Cassie were dating after a breakup. Kid Cudi would later come forward to confirm that he was, indeed, the man in question, and the incident did occur. Diddy quickly settled the lawsuit but accused Cassie of previously attempting to blackmail him for millions. Through his lawyer, he denied the allegations.

Then, earlier this year, a video of Diddy and Cassie surfaced, again thrusting them into infamy. The surveillance footage was from a hotel, showing Cassie making her way to an elevator before Combs is seen running after her, dragging her by her hair, punching her, and kicking her while she was on the ground. Cassie further speculated in her lawsuit that Diddy paid off certain hotel workers to suppress the video evidence.

This controversy resurfaced in the thick of Kendrick Lamar’s recent outpouring of diss tracks against Drake. After J. Cole swiftly removed himself from the brewing beef, fans hopped online to revisit the 2013 rumor of Cole and Combs getting into a physical altercation. The alleged event reportedly took place at an afterparty for the MTV Video Music Awards. Combs was said to have been liquored up when he confronted Cole about Lamar dubbing himself the “King of New York” on a track. K. Dot was also at the event, and Diddy allegedly attempted to pour a drink on him before Cole stepped in. Things escalated and became physical, claimed sources, but it was mainly pushing more than fisticuffs.

In 1991, the City College of New York became the scene of a fatal stampede. Diddy was all set for a promoted celebrity basketball game and impending concert in the packed gymnasium with a capacity of 2,730. However, fans stormed the location, and at least 5,000 people were in attendance, according to reports. Things became so out of control that officials stopped letting in guests as there wasn’t enough security to stave off the crowd. Closed doors didn’t stop those on the outside from trying to make their way in, eventually breaking down the barriers. The stampede resulted in over two dozen people being injured and nine others losing their lives. Much like Travis Scott faced at Astroworld, Combs was hit with several lawsuits from victims and family members of the deceased.

When young artists enter the music industry, many parents allow their children to live with high-profile producers or executives as they are developed. This happened with Bow Wow and Jermaine Dupri, Justin Bieber and Scooter Braun, and Usher with Diddy. Of the latter pair, in 2016, Usher reflected on his time at Diddy’s home when he was 13 and 14 years old. While on The Howard Stern Show, Usher recalled, “There were very curious things taking place.” He spoke about the late-night to early-morning parties Combs would host with his celebrity friends. The Grammy winner also suggested that the women who frequented these events flirted with the rising star.

Pride was illuminated by the Combs family when Diddy’s son Justin was accepted to the UCLA football team. However, in 2015, it was reported that Diddy got into a physical altercation with the then-assistant football coach, Sal Alosi. It was said that Diddy was less than thrilled when Alosi criticized Justin, leading to an argument later in the coach’s office. The mogul was accused of grabbing Alosi and throwing a kettlebell at another employee. It was rumored that Diddy had to be physically removed from the location, but Combs denied the allegations via his representative. Yet, Diddy was still arrested for assault, but charges were not filed against him. He would later speak on the incident during an interview with The Breakfast Club, which you can watch above.