Sketchy Things About Diddy Everyone Has Ignored For Years

The following article includes allegations of sexual abuse and assault.

Sean "Diddy" Combs was once on top of the world — until he wasn't. For decades, Diddy reigned supreme in the music industry through his record label, his own musical career, numerous business ventures, and an ambitious bid to establish a "media powerhouse." But it all came crashing down when he found himself entangled in a series of legal battles and a highly publicized FBI raid on his home.

Diddy's fall from grace reached a fever pitch in March 2024, when his properties in Miami and Los Angeles were raided by federal agents due to allegations of sex trafficking and distribution of illegal substances, among others. These raids came on the heels of multiple lawsuits accusing him of things like violence and rape — accusations that Diddy has consistently denied. "I did not do any of the awful things being alleged. I will fight for my name, my family and for the truth," he wrote in a statement on Instagram.

However, rumors of Diddy's questionable behavior aren't new. Long before these accusations, he was already a controversial figure. Allegations have swirled around him for years, ranging from putting artists in exploitative contracts to accusations of stealing music. To some people, Diddy has always been sketchy.

Despite continually bragging about his track record with women, Diddy appears to have developed an allergic reaction to the idea of walking down the aisle. While he has been involved in long-term relationships in the past, he has often eluded the topic of marriage, blaming his skeptical view of legal partnerships on a challenging upbringing.

"Just didn't want to do it," he said in an interview with Yung Miami in 2022 (via Revolt TV). "Just didn't wanna... never had a desire to get married, you know what I'm saying? When I was growing up, my father got killed when I was young, when I was two. And my mother, she just like never wanted to have men around."

His aversion to eternal commitment was on full display years earlier on "Watch What Happens Live," where he mentioned the massive responsibility and legal battles as major turn-offs. "I think you have to be ready for it. There's somebody else's heart involved and that's a lot of responsibility. And I don't want to be going to courts and having somebody be like, interfere in my relationships so I'd rather just do the Goldie Hawn," he said, referencing Hawn's famously unmarried but committed relationship with Kurt Russell. Diddy, however, isn't completely against formalizing relationships — he just prefers a different kind of agreement. "I will give a contract," he declared. "I will commit to a contract — a love contract."

Diddy may shy away from the whole institution of marriage, but he's embracing the concept of fatherhood with open arms. He has no problem fathering kids with multiple women, claiming that his kids are his pride and joy. As of this writing, there are seven children calling Diddy "daddy." He has a son with fashion designer Misa Hylton, four kids with his late ex Kim Porter, a daughter with his friend Sarah Chapman, and another daughter with a woman named Dana Tran.

But here's where it gets interesting — or questionable, depending on your take. In a 2018 interview on "The Breakfast Club," Diddy declared his ambition to have nearly a dozen kids, giving Nick Cannon a run for his money. "I'm trying to get to 10. It's a race," he joked, noting at the time that he only wanted to have children with his then-girlfriend Cassie, who later filed a case against him for sexual abuse. "Whatever is supposed to happen in the future is going to happen, but that's something that I want," he added. "I would only have it with my girl, of course."

Diddy's seventh child didn't come until the tail end of 2022, when he announced the birth of Love Sean Combs. "I'm so blessed to welcome my baby girl Love Sean Combs to the world," he wrote in a tweet. "Mama Combs, Quincy, Justin, Christian, Chance, D'Lila, Jessie and myself all love you so much! God is the Greatest!" Despite the public celebrations, details about his relationship with the mother of his youngest remain elusive.

At the center of Diddy's empire is the label Bad Boy Records, which he founded in 1993 and has attracted various artists like Notorious B.I.G., Faith Evans, and Mase. Diddy often touts himself as a mentor who fosters talent, but not everyone on his roster would agree — Mase being a prime example.

Their feud surfaced in 2020 when Diddy accepted an "Industry Icons" award at a 2020 pre-Grammys gala, where he asserted that "Black music has never been respected by the Grammys." Mase used it as an opportunity to call out Diddy's purported hypocrisy, revealing in a since-deleted Instagram post that Diddy has a history of exploiting his artists and trapping them in bad deals. "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," he said (via Rap Up), adding that he was paid a mere "peanuts." Diddy fired back, claiming that Mase owed him $3 million, but Mase, not one to back down, revealed in another deleted post that the witnesses to these shady deals, including Biggie, Craig Mack, and Black Rob, were no longer alive to back his claims. "And everybody else you made sign paperwork so they can't talk about what I'm talking about. I'm the only one with guts!" he said (via XXL).

It wasn't until 2023 that Mase and Diddy finally struck a deal allowing Mase to reclaim his publishing rights. That year, in an attempt to "lead by example," or perhaps perform penance, Diddy returned the music rights to his artists. "It's just doing the right thing," he told Variety. "It's not a publicity stunt or anything like that."

Apart from stiffing artists, Diddy has also been accused of stealing songs from them. One of his more outspoken naysayers is Aubrey O'Day, a former member of the girl band Danity Kane, which was formed on Diddy's MTV show "Making the Band" and was later signed to Bad Boy Records. According to her, Diddy has a history of swiping other artists' work and repurposing them for his own records. "Diddy took 3 songs from us and put them on his album," she wrote in a tweet in May 2023. "His song with Christina. His song with Nicole from PCD, it's still d woods voice saying it's bad boy b***h in beginning, & after love w Keri Hilson. All of those we recorded."

Up-and-coming rapper Swinderella made a similar claim, with an associate of hers revealing in an Instagram post that Diddy's track "Act Bad," was a carbon copy of her work. "The industry will really send people to bite your whole entire swagg! You never know who watching you, they not creative enough, they're not organic enough!" they dished. " Swinderella DID ACT BAD 2 YEARS AGO... DAMN you even stole the INTRO aesthetic." Diddy, for his part, didn't address the claims, and instead promoted the song as a collaborative masterpiece with City Girls and Fabolous. "We all teamed up together to drop the song of the summer," Diddy wrote in a since-deleted Instagram post (via The Source). "It's gonna be an Act Bad summer."

One of the most outrageous claims about Diddy concerns the infamous 1996 murder of Tupac Shakur. Duane "Keffe D" Keith Davis, reportedly the "shot caller" for the Southside Crips, who was present in the vehicle from which the fatal shots were fired, has pointed fingers at Diddy. He told the authorities that it was the producer who arranged the shooting of Tupac. In 2008, long before he was arrested for his alleged Tupac's murder, Keffe D claimed in a police interview that Diddy had offered him and an associate $1 million to kill the rapper. "He took me downstairs and he's like, 'Man, I wanna get rid of them dudes, man.'... I was like, 'We'll wipe their a** out quick, man. It's nothing,'" he said (via LA Weekly).

But Diddy was adamant that he had nothing to do with Tupac's death. "This story is pure fiction and completely ridiculous," he told the outlet. Years later, when Eminem referenced the allegations in the track "Killshot," Joe Budden noted in his podcast that Diddy told him that it was "handled" without elaborating further. "Nothing to speculate about, nothing to talk about. Puff said it's in his hands and he said I can say it," Budden said (via Essence). "He said, 'There's nothing to say about it. It's in my hands. He wild.'"