Diddy arrest punctuates long history of legal troubles: Unraveling old lawsuits, allegations

For Sean "Diddy" Combs, the fall from both grace and luxury has been precipitous.

Last week, the hip-hop pioneer and fashion world staple exchanged his sprawling mansions for a dank prison cell in Brooklyn, New York, after being charged with racketeering, sex trafficking and transportation to engage in prostitution. Combs, 54, has been denied bail on the grounds that he is both a flight risk and could coerce witnesses.

The uneventful arrest of the mogul at New York's Park Hyatt hotel was hardly a surprise. While consistently protesting his innocence, Diddy in recent months has been hit with an avalanche of lawsuits, including from his ex-girlfriend singer Cassie Ventura, former Danity Kane member Dawn Richard and model Crystal McKinney.

But combing through the past three decades of the New York-born former altar boy's life finds a steady stream of legal entanglements that seem to presage his current predicament. These run from chaos at concerts and demands for child support, to threats with baseball bats and legal entanglements with corporate giants.

Although 1999 was a particularly troublesome year for Diddy, his saga truly begins in the early '90s, when the 22-year-old upstart producer at Uptown Records organized an event that quickly went off the rails.

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1991: NYC celebrity basketball event results in stampede, killing 9

Billed as a charity event to benefit AIDS education, the celebrity basketball game organized in the final days of 1991 promised fans paying $20 each a hoops battle featuring the likes of Boyz II Men, Run-DMC, Jodeci, Heavy D and Big Daddy Kane.

The event, held in a basement college gym in Manhattan, quickly got out of control, with 5,000 people, many without tickets, pushing their way into a space meant for half those numbers. The ensuing stampede resulted in nine deaths. Although no criminal charges were ever brought against Combs for mishandling the event, he was fired by Uptown Records and was part of civil suits related to the incident.

1999: Assault and harassment of record exec Steve Stoute

Nas' 1999 "Hate Me Now" music video featured a cameo by Diddy, who appeared Christ-like on a cross. But Combs suddenly decided he did not want that scene in the video, and took that complaint to Interscope executive Steve Stoute. What followed was a beatdown, Stoute said.

"One minute I'm in the middle of a meeting," Stoute told the Los Angeles Times, "and the next minute I'm down on the floor and Puffy and his guys are kicking and pounding me."

Combs pleaded guilty to a minor charge of harassment and then made a $500,000 payment to Stoute for so-called management fees.

1999: NYC nightclub shooting involving JLo and Shyne

In perhaps the most alarming Diddy incident of 1999, the rapper was at a Manhattan club with then-girlfriend Jennifer Lopez. Diddy and his bodyguard Anthony "Wolf" Jones allegedly got into a disagreement with rapper Moses "Shyne" Barrow, and the resulting gunfight left three people injured. One was Natania Reuben, who has consistently claimed Diddy was one of the men shooting.

After a police chase, Diddy, Lopez, Jones and Barrow were all briefly arrested. The ensuing jury trial found only Barrow serving prison time — nine years — for charges that included criminal possession of a weapon.

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2001: Alleged assault of Michigan TV host

In 2001, Michigan television host Roger Mills sued Combs after an alleged attack following a 1999 interview. Mills' then-attorney claimed Combs approached the host about an interview at WCHB-TV in Detroit but became angry when, during the interview, Mills asked Combs about claims the producer contributed to the death of The Notorious B.I.G.

The New York rapper, born Christopher Wallace, was gunned down in Los Angeles in 1997, just six months after a similar drive-by shooting death of West Coast rapper Tupac Shakur. After WCHB host Mills asked Combs about his ties to the incident, Combs' representative requested the tape of the interview and, when Mills refused, Combs' entourage attacked the host and took the tape, the host claimed. A spokeswoman for Combs denied the claims and accused Mills of extorting the rapper. At a 2004 civil trial, the jury ruled in favor of Combs.

2001: Kim Porter sues for child support

After a multi-year dispute over child support for their son Christian, Diddy settled the case by agreeing to pay model Kim Porter a reported five-figure monthly sum to provide for their child's education and medical expenses until the then-3-year-old turned 21.

Diddy has fathered six children by four different women. His children also include adopted son Quincy, 33, whom Porter shared with Al B. Sure; Justin, 30, whose mother is Misa Hylton; Christian, now 26; Chance, 18, born to Sarah Chapman; D'Lila and Jessie, 17, born to Porter; and Love, 1, born to Dana Tran.

2003: Diddy allegedly threatens business partner with baseball bat

Kirk Burrowes, a former executive at the successful '90s hip hop label Bad Boy Entertainment, which Combs founded in 1993, sued his former boss in 2003 claiming that in 1996 the rapper had used a baseball bat to intimidate Burrowes into signing away his rights to company stock.

In his $25 million lawsuit, Burrowes claimed that although he was fired in 1997, Combs had promised him a share in company profits. Lawyers for Combs responded by calling the suit "pure fantasy." The lawsuit was thrown out in 2006.

2007: Alleged assault of man outside nightclub

In 2007, Gerard Rechnitzer sued Combs for punching him after a night out at a Hollywood club. He claimed the incident happened after he approached Combs while he was talking to Rechnitzer's girlfriend.

"It is just another example of an opportunist seeking to fabricate a lawsuit based on a flat-out lie to try to take advantage of Mr. Combs' celebrity status," Combs' lawyer said at the time. The lawsuit was settled for an undisclosed amount in 2008.

2010: Bad Boy music exec sues for age discrimination

Former Bad Boy Records music executive Francesca Spero filed a $12 million lawsuit against Combs for age discrimination in 2010, alleging the rapper fired her because of her age and disability. Spero, then 51, claimed the longtime relationship between the two soured after her hip surgery in 2008. The lawsuit was settled for an undisclosed amount in 2011.

2015: Alleged assault of UCLA coach

In 2015, then-University of California, Los Angeles coach Sal Alosi claimed the rapper attacked him with a kettlebell after Alosi kicked his son Justin Combs, then a redshirt junior on UCLA's football team, out of practice. Combs was charged on multiple counts for the headline-making incident, including assault with a deadly weapon. Felony charges against Combs, who claimed self-defense, were dropped shortly after.

2017: Personal chef sues for sexual harassment

Combs' former personal chef, Cindy Rueda, sued the rapper for sexual harassment in 2017. Rueda claimed in two separate 2015 incidents that, after he berated her for being late, she walked in on Combs having sex while attempting to serve him breakfast and that the rapper and her other boss made sexual comments about the size of her lips. She also claimed she was not properly paid for overtime hours or travel. The lawsuit was settled in 2019 for an undisclosed amount.

2023: Diddy sues Ciroc owner, severs ties

Combs' ties with former business partner and liquor powerhouse Diageo went left when the label head sued the spirits brand for racial discrimination in 2023, months before the recent wave of civil suits against him.

Combs claimed the London-based company didn't make vowed investments in the liquor brands Cîroc and DeLeon Tequila which he promoted and co-owned, respectively. Combs claimed the company treated the brands as second-rate "urban" products and that leadership told him race was a factor in limiting distribution to certain neighborhoods. Diageo claimed the relationship soured after Combs failed to make investments in DeLeon.

Combs dropped his lawsuit and severed ties with the company in January.

Present-day: Sexual assault lawsuits, raids, trafficking indictment

Combs' latest wave of legal trouble was spurred by a bombshell lawsuit filed by ex-girlfriend Cassie Ventura in November. The singer accused the mogul of rape, sex trafficking and physical abuse, with both settling for an undisclosed amount the next day. Other lawsuits include one filed by "The Love Album" producer Rodney "Lil Rod" Jones Jr. in February, accusing Combs of orchestrating "a sex-trafficking venture."

Other recent lawsuits have come from former model Crystal McKinney, an unnamed 17-year-old girl, then-fashion student April Lampros and then-college student Joi Dickerson-Neal. Law enforcement raided Combs' homes as part of a federal investigation in March.

And earlier this month, Dawn Richard, formerly of the trio Diddy Dirty Money, sued Combs on 21 counts of sexual assault and battery, sex trafficking and copyright infringement. Combs' arrest and indictment came days later.