Diddy charges are just the latest in a long history of legal problems

For Sean “Diddy” Combs, the fall from grace and luxury was steep.

Last week, the hip-hop pioneer and fashion icon traded his sprawling mansion for a dank jail cell in Brooklyn, New York, after being charged with racketeering, sex trafficking and transportation for the purpose of prostitution. Combs, 54, was denied bail on the grounds that he was both a flight risk and a potential witness harassment agent.

The mogul's uneventful arrest at New York's Park Hyatt hotel came as little surprise. Although Diddy has repeatedly protested his innocence, he has been hit with an avalanche of lawsuits in recent months, including from his ex-girlfriend, singer Cassie Ventura, former Danity Kane member Dawn Richard and model Crystal McKinney.

But if you look back over the last three decades of the New York-born former altar boy's life, you'll find a steady stream of legal entanglements that seem to foreshadow his current predicament, ranging from chaos at concerts and demands for child support to threats with baseball bats and legal entanglements with major corporations.

Although 1999 was a particularly difficult year for Diddy, his story actually begins in the early '90s, when the 22-year-old aspiring producer from Uptown Records organized an event that quickly got out of hand.

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1991: Celebrity basketball event in New York leads to mass panic, 9 people die

The celebrity basketball game, organized in the last days of 1991, was announced as a charity event for AIDS awareness and promised fans a basketball battle with stars such as Boyz II Men, Run-DMC, Jodeci, Heavy D and Big Daddy Kane for every dollar.

The event, held in a basement gymnasium of a Manhattan college, quickly spiraled out of control. 5,000 people, many without tickets, crowded into a space designed to hold half that number. The stampede that ensued left nine people dead. Although Combs was never charged for mismanagement of the event, he was fired from Uptown Records and was involved in civil suits related to the incident.

1999: Assault and harassment of record executive Steve Stoute

Nas' 1999 music video for “Hate Me Now” featured a cameo by Diddy, who was seen in a Christ-like depiction on the cross. But Combs suddenly decided he didn't want that scene in the video and took the complaint to Interscope executive Steve Stoute. What ensued was a brawl, Stoute said.

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

Combs pleaded guilty to a minor charge of harassment and subsequently paid Stoute $500,000 as a so-called management fee.

1999: Shooting in a New York nightclub involving JLo and Shyne

Perhaps the most disturbing Diddy incident of 1999 occurred when the rapper was at a Manhattan club with his then-girlfriend Jennifer Lopez. Diddy and his bodyguard Anthony “Wolf” Jones allegedly got into an argument with rapper Moses “Shyne” Barrow, and the resulting shootout left three people injured. One of them was Natania Reuben, who repeatedly claimed Diddy was one of the men who fired the shots.

After a police chase, Diddy, Lopez, Jones and Barrow were briefly arrested. In the subsequent trial, it was determined that only Barrow would serve a prison sentence of nine years. The charges included illegal possession of weapons.

Former Bad Boy artist Shynesays Diddy “ruined” his life: “I defended him”

2001: Alleged attack on a Michigan television presenter

In 2001, Michigan television host Roger Mills sued Combs following an alleged assault following a 1999 interview. Mills' attorney at the time claimed that Combs approached the host about an interview at WCHB-TV in Detroit, but became angry when Mills questioned Combs during the interview about claims that the producer contributed to the death of The Notorious BIG.

The New York rapper, born Christopher Wallace, was gunned down in Los Angeles in 1997, just six months after a similar incident in which West Coast rapper Tupac Shakur was shot from a passing car. After WCHB host Mills asked Combs about his connection to the incident, Combs' representative demanded 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 allegations and accused Mills of extorting the rapper. At a civil trial in 2004, the jury found in Combs' favor.

2001: Kim Porter sues for child support

After a multi-year dispute over child support for her son Christian, Diddy reached an agreement with model Kim Porter, agreeing to pay a five-figure sum each month to cover her son's education and medical expenses until the then three-year-old turned 21.

Diddy has fathered six children with four different women. His children also include adopted son Quincy, 33, whom Porter has with Al B. Sure; 30-year-old Justin, 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 threatened 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 the rapper intimidated Burrowes with a baseball bat in 1996 and forced him to give up his rights to company stock.

In his $25 million lawsuit, Burrowes claimed that Combs promised him a share of the company's profits despite his firing in 1997. Combs' lawyers called the lawsuit “pure fantasy.” The suit was dismissed in 2006.

2007: Alleged attack on a man outside a nightclub

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

“It is just another example of an opportunist attempting to construct a lawsuit based on an outright lie in order to capitalize on Mr. Combs' celebrity status,” Combs' attorney said at the time. The lawsuit was settled in 2008 for an undisclosed amount.

2010: Bad Boy's music manager sues the band for age discrimination

Former Bad Boy Records music executive Francesca Spero filed a $12 million age discrimination lawsuit against Combs in 2010, claiming the rapper fired her because of her age and disability. Spero, then 51, claimed the pair's long-term relationship fell apart after her hip surgery in 2008. The suit was settled in 2011 for an undisclosed amount.

2015: Alleged attack on UCLA coach

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

2017: Private chef sues for sexual harassment

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

2023: Diddy sues Ciroc owner and breaks ties

Combs' ties with his former business partner and spirits giant Diageo were strained when the label boss sued the spirits brand for racial discrimination in 2023, months before the recent wave of civil lawsuits against him.

Combs claimed the London-based company failed to make promised investments in the Cîroc and DeLeon tequila spirits brands, which he marketed or co-owned. Combs claimed the company treated the brands as second-rate “urban” products and that management told him that race was a factor limiting distribution to certain neighborhoods. Diageo claimed the relationship soured after Combs failed to make investments in DeLeon.

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

Present: Trials for sexual assault, raids, charges of human trafficking

Combs' latest wave of legal troubles was sparked by a high-profile lawsuit filed by his ex-girlfriend Cassie Ventura in November. The singer accused the mogul of rape, sex trafficking and physical abuse, and both settled 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 organizing “a sex trafficking enterprise.”

Other recent complaints came from former model Crystal McKinney, an unnamed 17-year-old girl, then-fashion student April Lampros and then-college student Joi Dickerson-Neal. In March, law enforcement officials raided Combs' homes as part of a federal investigation.

And earlier this month, Dawn Richard, formerly of the trio Diddy Dirty Money, sued Combs for 21 counts of sexual assault, sex trafficking and copyright infringement. Combs was arrested and charged just days later.

Diddy charges are just the latest in a long history of legal problems

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