Sean Combs — originally known as Puff Daddy, and now known as Diddy, or “Brother Love”  — is one of the richest hip-hop stars in the world, but he has always been somewhat of a controversial figure. He began as an intern at Uptown Records under legendary executive Andre Harrell before quickly rising into the A&R department, where he was responsible for hit records by the likes of Father MC and Mary J. Blige. His ambition, however, soon saw him ousted from the label; as he later explained to Oprah Winfrey, “I didn’t understand protocol or workplace politics … I got fired because there can’t be two kings in one castle” (via Yahoo! News).

He went on to found Bad Boy Records, quickly making his mark producing records by the likes of Craig Mack and Notorious B.I.G., despite having a production style that could charitably be described as “the unapologetic yoinking of other, more talented artists’ entire compositions.” He soon got behind the mic himself, and as the platinum records and Grammy awards rolled in, so did the controversy — from accusations of involvement in the non-fatal 1994 shooting of Tupac Shakur, to the infamous 1999 nightclub shooting for which Bad Boy associate Shyne went to prison, to rumblings about poor business practices. In 2023, a number of former associates came forward accusing Combs of a wide range of awful behavior, from cheating artists out of money to sexual abuse — behavior which may help to explain why there seem to be a lot of stars who simply can’t stand Sean “Diddy” Combs.

CASSIE VENTURA

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Cassandra Ventura, professionally known as Cassie, received her big break in music when she met Sean Combs in 2005 at the age of 19. Before long, she was signed to Bad Boy and in a romantic relationship with Combs — one that, according to a lawsuit filed by Ventura in 2023, quickly turned into a nightmare. Combs, the singer alleged, was violent, abusive, and controlling in the extreme during their time together; she claims he beat her, sexually assaulted her, and forced her to have sex with male sex workers while he watched, among other horrifying things. Ventura further claimed that Combs kept her pliant with drugs and alcohol, had associates hunt her down whenever she attempted to leave, and once even followed through on a terrifying threat — allegedly blowing up the car of rapper Kid Cudi, whom Ventura briefly dated during a separation from Combs.

In November 2023, Ventura settled with Combs out of court for an undisclosed amount, and while Vulture reports that Combs’ attorney was quick to point out that “a decision to settle … is in no way an admission of wrongdoing,” Ventura heavily implied in a statement (via The New York Times) that said decision also did not constitute a revocation of her claims. “I have decided to resolve this matter amicably on terms that I have some level of control [over],” she said. “I want to thank my family, fans and lawyers for their unwavering support.”

CURTIS JACKSON, AKA 50 CENT

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Curtis “50 Cent” Jackson has never been shy with his opinions about anything, least of all Sean Combs, whom the rapper has — to put it politely — never really cared for. Jackson first made his feelings for Combs widely known on his 2006 song “Hip Hop,” which flatly accused Combs of being involved with the tragic murder of his own protégé, Notorious B.I.G.; more recently, he has just as flatly stated that Combs was also responsible for the murder of Tupac Shakur a year prior. This, however, just scratches the surface of Jackson’s problems with Combs.

When multiple former associates came forward in 2023 with claims that Combs sexually assaulted them, Jackson quickly announced via X (formerly Twitter) that his film and television production company would be producing a documentary about the allegations — and since making that announcement, he has not missed an opportunity to troll Combs over his mounting troubles. When Combs’ Los Angeles and Miami homes were raided by Homeland Security as part of the investigation into those allegations in 2024, Jackson once more took to X to remark on the development with characteristic cheekiness. “Now it’s not Diddy do it, it’s Diddy done,” he posted. “They don’t come like that unless they got a case.”

JAGUAR WRIGHT

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R&B singer Jaguar Wright has had minor success as a solo artist, and arguably made more waves as a sometime member of legendary Philadelphia outfit The Roots and as a featured artist alongside the likes of Jay-Z, Lauryn Hill, and others. She’s been in the music industry for over 20 years, and she has never been shy about calling out such artists as Erykah Badu, Talib Kweli, Common, and others for alleged skeevy behavior. When it comes to Sean Combs, though, Wright is pretty convinced that his behavior transcends the merely skeevy. In an infamous 2022 interview, she implied strongly that she believes Combs’ ambition to know literally no bounds.

The interview, with Real Lyfe Productions, came shortly after fellow R&B singer and former Uptown Records artist Al B. Sure woke up from a two-month coma and was slowly recovering from a host of medical problems. In it, Wright points out that Uptown started with five people: Andre Harrell, his longtime assistant (and Combs’ longtime girlfriend) Kim Porter, beloved MC Dwight “Heavy D” Myers, Al B. Sure, and Combs himself. She then deadpanned, pausing in between each name for emphasis: “Kim is dead. Heavy D is dead. Andre Harrell is dead. The only two left are [Combs] and Al, and Al almost died.” She further asserted that every one of those five individuals not named Sean Combs were working on books about their experiences in music at the time of their death or health crisis — leaving the interviewer, and the viewer, to draw their own conclusions.

KANYE WEST

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Rapper and producer Kanye West is a man who famously doesn’t care what anyone thinks about him; indeed, it sometimes seems as though he doesn’t care much about objective reality. Case in point: In late 2022, West was seen wearing a T-shirt emblazoned with the slogan “White Lives Matter,” which shocked his fans due to the fact that this slogan obviously constitutes a mockery of the anti-police brutality Black Lives Matter movement, not to mention the even more obvious fact that West is quite clearly Black. West even attempted to market the shirts before being hilariously and appropriately stymied by the copyright’s ownership by two Black men, but not before drawing the ire of his former friend Sean Combs, who received a heaping helping of West’s own ire in response.

In a lengthy text exchange which West (of course) subsequently posted to Instagram, Combs showed surprising restraint in asking West if he might reconsider this endeavor, a request which garnered a profane and often puzzling response from West (via XXL). West wrapped up the conversation by promising to “use [Combs] as an example” before declaring “war” on his old buddy. So far as anyone knows, West never got around to lobbing any rockets at Combs, but the dust-up certainly appeared to end their friendship. Nearly a year and a half later in March 2024, Combs asked for a face-to-face meeting with West at the Rolling Loud festival, and was soundly rebuffed.

MARK CURRY

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The phenomenon of artists getting chewed up and spit out by the music industry is certainly nothing new, but former Bad Boy songwriter and performer Mark Curry could make a case for having been screwed over in extra-special fashion. In fact, he has: In his 2009 book “Dancing With the Devil,” he spelled out how, despite having written or co-written hits like “Come With Me” and “Bad Boy for Life” for Sean Combs, he never saw his efforts translate to any significant amount of money. Continuing to roll a 1992 Honda Accord while your boss magically turns words that you wrote into diamond-studded Bentleys would make anyone a little bitter, but in light of Combs’ recent legal troubles, Curry has gone a bit further than to accuse him of being a cheapskate.

In December 2023, Curry gave an interview to The Art of Dialogue in which he was asked about accusations made to the same outlet by Gene Deal, Combs’ former bodyguard. Among these were that Combs beat Kim Porter badly enough to require hospitalization, and Curry confirmed this, and more: “Busted her nose, man,” he said, adding that Combs was known to wiretap Porter’s phone and hide recording devices in her home. “When you see someone doing that,” he said, “you can imagine everything else they do.” He went on to opine that the crimes Combs is accused of are completely in character for him, saying, “I think he’s very capable of doing it … that’s who he is. That’s what comes with power, that’s what comes with arrogance.”

LIL ROD

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Producer Rodney “Lil Rod” Jones also counts himself among those whose business relationships with Sean Combs ended rather unsatisfactorily. In February 2024, he took to TikTok to describe the brutal conditions he was subjected to while working on Combs’ Grammy-nominated “The Love Album: Off the Grid,” which included grueling hours and impossible deadlines for very little compensation; in addition, he claimed Combs was actively attempting to cheat him out of publishing rights on the project. This, however, was just the tip of the iceberg of Jones’ grievances.

The very next month, Jones filed a lawsuit against Combs claiming that the mogul subjected him to sexual harassment, including frequent groping and coerced participation in sex with sex workers. Even this, though, was not his most shocking allegation — that would be his assertion that, in 2022, either Combs or his son Justin shot a man identified only as “G,” a 30-year-old friend of Justin’s, in the bathroom at a Los Angeles recording studio. Jones claims to have personally carried the wounded man to the ambulance, and further stated that he was instructed directly by Combs to lie to the authorities, telling them that the man had been wounded in a drive-by shooting outside the studio. The suit also implies that the LAPD might have been complicit in a cover-up: “As of the date of this filing, [the LAPD has not] released any official reports surrounding this shooting. There has been no body camera footage, and no 911 call recording,” it reads, adding that the victim seems to have disappeared (Via Yahoo! News).

WENDY WILLIAMS

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Radio and TV host Wendy Williams was a significant part of the hip-hop landscape for many years, and for just about all of those years, she had a relationship with Sean Combs that could be described as “super-contentious.” Williams, who has always had an ear for juicy celebrity gossip, got on Combs’ bad side very early in her career, when — as a personality on New York radio station Hot 97 — she apparently said something that displeased the mogul. On a 2019 episode of “The Wendy Williams Show,” she recounted how Combs had sent the members of Total — an all-girl R&B group signed to Bad Boy — to the radio station to jump her. (It didn’t work out; Williams’ boyfriend at the time defused the situation.)

Not long afterward, Williams says, Combs went so far as to get her fired from Hot 97 when she came into possession of a photo showing Combs in an intimate situation with another man while on vacation; of course, she landed on her feet, but she continued to blame Combs for trying to ruin her career for years afterward. In her 2004 book “The Wendy Williams Experience,” she wrote of Combs, “The hell he put me through, I will never forget.” The two appeared to patch things up when Combs appeared on a 2017 episode of her show, but that didn’t stop Williams from speculating about his relationship with Cassie Ventura just a year later, saying, “I believe he probably treated her, at some particular point, like a possession” (via Atlanta Black Star).

AUBREY O’DAY

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In 2002, Sean Combs decided to expand into reality television by taking over the MTV series “Making the Band,” which had run for one season under the infamous boy band mogul Lou Pearlman. Combs’ iteration of the series failed to make stars out of hip-hoppers Da Band on its first attempt, but its second produced something closer to a viable product in girl group Danity Kane, which scored a pair of No. 1 albums and two Top 10 singles during its relatively brief existence. Some members of the group, though, were less than enamored with the man who handed them their careers — most notably Aubrey O’Day, who described her experience working with Combs in less than rosy terms.

In a 2019 conversation with Variety, O’Day described Combs as difficult in the extreme to work with, for reasons including but not limited to his almost-fanatical perfectionism. “We were scared to death with what would happen with [Combs] each day,” she said. “I experienced everything from [racial comments] to sexism, and a lot of it was scary.” When Combs’ homes were raided by federal agents, O’Day posted an Instagram story with a few succinct remarks. “What you sow, you shall reap,” she wrote. “I pray this emboldens all of us victims to finally speak on what we have endured” (via People).

MASE

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Mason “Mase” Betha (often stylized as “Ma$e”) was one of Bad Boy’s biggest success stories in the late ’90s. Even before his first album had been released, he’d been featured as a guest rapper on smash singles such as “It’s All About the Benjamins,” “Mo’ Money, Mo’ Problems,” and “Can’t Nobody Hold Me Down.” His debut LP “Harlem World,” which dropped in 1997, shot straight to No. 1 and produced the Top 10 single “What You Want” — but just as quickly as Mase burst onto the scene, he exited the music industry, retiring in 1999 to become an ordained minister. He has made brief returns to music in the intervening years, releasing the album “Welcome Back” in 2004 — and in 2022, he released the track “Oracle 2,” in which he lyrically rips Sean Combs up one side and down the other.

The gist of Betha’s beef with Combs is the latter’s tendency to rip off his artists in addition to being a magnet for trouble, claims that he expounded on in a March 2024 episode of fellow rapper Cam’Ron’s “It Is What It Is” podcast. “Everything now that we see playing out,” he said, referring to Combs’ current legal troubles, “was all the things I escaped … even though I made those decisions and it cost me money.” In an episode that posted the day after Combs’ homes were raided, Betha was also not shy about his prediction with respect to what awaits Combs in the near future: “Reparations is getting closer and closer.”

TANIKA RAY

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Television personality Tanika Ray made her bones as an actress and entertainment journalist, but she got her start as a backup dancer for Sean Combs and his Bad Boy stable. She has had occasion to cross paths professionally with Combs a time or two in the years since her Bad Boy experience, and while she has yet to share much in the way of details about that experience, an Instagram post she made as Combs’ legal troubles began to mount was extremely telling.

In it, she laments that nothing would have come of it “if I [had] told my story in 1996.” She went on to relate that she quickly learned that in order to avoid trouble, it was wise to simply avoid Combs. “I just knew to avoid him at all costs,” she wrote. “Yes I danced for him and kept my space. I was on [an] airplane [with him] and kept my space. I interviewed him for his projects and kept my space.” She went on to express what seems to be a prevailing sentiment among those who have known Combs for a long time: “Nothing that is happening is surprising … Shame on all those men that let this continue.”

DRAKE

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The bad blood between Sean Combs and Toronto rapper Drake seems to stem from what Combs would later call a simple misunderstanding. It seems that, in 2014, Combs and Drake were involved in an altercation at a Miami nightclub — a fight that was reportedly over the song “0 to 100/The Catch-up,” the track for which producer Boi-1da had pitched to Combs before it ended up in the hands of Drake (and landed him a Grammy nomination). Multiple sources reported to MTV and TMZ that physical blows had been thrown, with some even stating that Drake had ended up in the hospital when he aggravated an old injury during the fight.

According to MTV, Combs would later insist during an interview with radio station Power 105.1 that the fight had not actually been physical and that he had nothing but respect for Drake — but if that’s true, those warm fuzzy feelings did not appear to be mutual, as Drake fired off a Combs diss track entitled “4PM in Calabasas” in 2016. Since then, Drake has not had much to say about Combs. In 2022, though, it was reported by none other than Kanye West (during an appearance the Lex Fridman Podcast) that the two had nearly come to blows once again when they ran into each other backstage at his fashion show — and that Jay-Z, of all people, had stepped in between the two to break it up. Oh, those crazy rap kids!

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