Celebs Who Can't Stand Sean 'Diddy' Combs

The following contains mentions of sexual and physical assault.

The raids on Sean "Diddy' Combs" homes were a bad omen for the rapper in more ways than one. As his legal woes have continued to mount, it seems that some of his longtime enemies are growing more emboldened to speak out against him. The allegations about Diddy engaging in some seriously heinous criminal acts have also reminded his critics about past instances when his behavior was allegedly unsavory.

At the forefront of everyone's minds is Casandra "Cassie" Ventura, whose civil lawsuit against Diddy made her feelings about the Bad Boy Records founder abundantly clear. In court documents, she accused her ex of rape and physical abuse. "Adding insult to injury, Mr. Combs used illegal substances and threats of violence to force Ms. Ventura into repeated unwanted sexual encounters with male sex workers," Cassie's complaint read. According to the "Love a Loser" singer, the way Diddy allegedly tormented and abused her caused her so much anguish that she now suffers from PTSD.

While Diddy moved to quickly settle Cassie's lawsuit out of court, it wouldn't be the last he heard from his ex's attorney. After Homeland Security raided Diddy's properties, Cassie's lawyer, Douglas Wigdor, expressed his support for the investigation. "Hopefully, this is the beginning of a process that will hold Mr. Combs responsible for his depraved conduct," Wigdor told Page Six. He's not the only one who had something to say about the raids — some of Diddy's most famous foes seem to be rooting for his downfall.

Aubrey O'Day wants more victims to come forward

Upon learning about the Diddy raid, former Danity Kane member Aubrey O'Day suggested that karma was at play in a post on her Instagram Story. "What you sow, you shall reap," she wrote (via Page Six). She had previously used the same social media platform to express disappointment over Diddy avoiding his day in court by settling his lawsuit with Cassie confidentially. "Money > accountability. Every time," she wrote (via The Blast).

O'Day's beef with Diddy goes way back to 2005 when they appeared together on Diddy's MTV reality series "Making the Band 3." The two often clashed after Diddy and his fellow judges decided to offer O'Day a spot in the group that became Danity Kane — and Diddy eventually fired her. "I wasn't willing to do what was expected of me, not talent-wise, but in other areas," she said of her firing on the "Call Her Daddy" podcast. She also accused Diddy of making sexually inappropriate remarks about her during her time with Danity Kane. "Diddy was making comments like, 'Oh, now like you're f***able. You look right, I can f*** you now,'" she recalled on the "No Jumper" podcast. 

According to O'Day, Diddy did Danity Kane dirty by pocketing tens of millions from their work. "We didn't even see a penny of that and we were in thongs and five-inch heels for years of our lives on stage," she said on the "Only Stans" podcast.

Mase accused Diddy of shady business dealings

Mason "Mase" Betha was featured on the 1997 Bad Boy Records hit "Mo' Money, Mo Problems" alongside Diddy and the late Biggie Smalls. But if what he once said about Diddy is true, Mase never made enough money to worry about the problems that come along with it while he was signed to Diddy's record label. At the 2020 Grammys, Diddy won an Icon Award and delivered a speech that rubbed Mase the wrong way. After Diddy slammed the recording industry for not giving Black artists enough recognition and respect, Mase accused Diddy of being a hypocrite by failing to extend some of that courtesy he was demanding to his own artists.

In a since-deleted Instagram post, Mase revealed that Diddy only paid him $20,000 for his masters when he purchased it over two decades ago. Mase claimed that he tried to buy his catalog back just days before the Grammys for $2 million, but Diddy refused his offer. "This is not Black excellence at all. When our own race is enslaving us. If it's about us owning, it can't be about us owning each other," Mase wrote (via Hip-Hop Lately). Mase also had something to say about Diddy's mansions getting raided by Homeland Security, and he was not sympathetic about federal agents trashing his homes. "Reparations is getting closer and closer. ... the big payback," he said on his "It Is What It Is" podcast.

Fiddy vs. Diddy

"Window Shopper" rapper 50 Cent fired some lyrical shots at Diddy back in 2006 when he dropped "The Bomb." In the song, 50 Cent suggests that Diddy knows who killed Biggie Smalls. Fiddy's beef with the hip-hop mogul also seems to be related to assumptions he's made about Diddy's sexuality. In a 2018 appearance on "The Breakfast Club," he recalled getting outraged when Diddy offered to take him shopping. "That's what a guy says to a girl!" he exclaimed.

The "In da Club" rapper seems to revel in every disastrous headline that Diddy gets hit with. After Cassie filed her lawsuit against Diddy in 2023, 50 Cent took to Instagram to have a good laugh over how her disturbing allegations were damaging his rival's rep. "Damn brother love, brother love, brother love, you out here looking CRAZY AS A MF. LMAO," he wrote. ("Brother Love" is one of the many nicknames Diddy has given himself). 50 Cent has also shared a mock-up of a documentary poster mocking Diddy. According to the "21 Questions" singer, a special about his archenemy's scandals titled "Diddy do it?" has the potential to be a massive hit. Fiddy employed this same punny wordplay when sharing his thoughts about what the raid on Diddy's properties means. "Now it's not Diddy do it, it's Diddy done," he tweeted. "They don't come like that unless they got a case."

Kanye West got mad when Diddy criticized his merch

If there's one thing Kanye West can't stand, it's when someone questions his business acumen. During his Yeezy Season 9 show in 2022, Ye showcased a shirt with the words "White Lives Matter" emblazoned on the front. Diddy reacted to the design in a since-deleted Instagram video, deeming it a message he couldn't get behind because it minimized the Black Lives Matter movement. "Don't wear the shirt. Don't buy the shirt," he begged his followers (via Complex). Shortly after filming the video, Diddy found himself on the receiving end of one of Ye's rageful social media rants. Ye posted what he claimed were screenshots of text messages he had exchanged with Diddy about their clothing conflict. "Nobody gets in between me and my money," one of Ye's messages read. He also suggested that Diddy was being influenced by "Jewish people" who told him to contact Ye. "I told you this was war," read another ominous text.

At one point, Ye called Diddy a "fed." He did this again during a 2022 "Drink Champs" interview, which got removed from YouTube because of his antisemitic comments. The rapper shared a conspiracy theory that some of his peers — Diddy included — were snitching on other celebrities to the government to avoid getting charged with crimes themselves. Ye suggested Diddy and Meek Mill were targeting him specifically, and he shared a message for them: "Y'all need to shut the f*** up about me!"

Kimora Lee Simmons said that Diddy threatened her

Kimora Lee Simmons was close friends with Diddy's late ex Kim Porter, who died in 2018. However, it sounds like it wasn't exactly easy for Kimora to accept her friend's longtime partner. According to a 2004 New York Magazine profile of Kimora, she once had a verbal altercation with Diddy that took a sinister turn when the rapper warned her that he was going to strike her. Luckily, this didn't happen. "And I was pregnant! The moron!" Kimora recalled. It took a groveling apology for the "Kimora: Life in the Fab Lane" star to forgive Diddy. But even after she did, she seemed to throw some subtle shade at him for modeling himself on her husband, Def Jam founder Russell Simmons. "I respect him for being a fierce entrepreneur, and I appreciate knowing that everything he does is emulating my husband," she said.

Kimora hasn't directly addressed the numerous allegations against Diddy as of this writing, but some netizens were convinced that a cryptic post on her Instagram Story was a dig at him. After Cassie filed her lawsuit against Diddy, Kimora wrote, "As you sow, so shall you reap." This simple sentence had users on X believing that Kimora had some serious tea to spill. "That woman knows everything," one tweet read. Another person wrote, "Everybody betta beef up their security, expeditiously."

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).