Sean “Diddy” Combs has experienced a rapid decline from fame and wealth.

Last week, this influential figure in hip-hop, now 54, traded his luxurious lifestyle for a gloomy prison cell in Brooklyn, New York. He faces serious charges including racketeering, sex trafficking, and facilitating prostitution. Diddy has been denied bail as authorities deem him a flight risk and a potential witness tamperer.

His arrest at New York’s Park Hyatt hotel came as no shock. Despite repeatedly asserting his innocence, Diddy has recently been overwhelmed by numerous lawsuits, notably from singer Cassie Ventura, former Danity Kane member Dawn Richard, and model Crystal McKinney.

A look back over the last thirty years reveals a continuous stream of legal conflicts for Diddy, ranging from concert chaos and child support disputes to physical threats and corporate legal battles.

While 1999 was particularly tumultuous for Diddy, his troubles began in the early 1990s when as a 22-year-old emerging producer at Uptown Records, he organized a disastrous event.

1991: Celebrity Basketball Game Ends in Tragedy

The celebrity basketball game, which was touted as a charity event to raise funds for AIDS education, took place in late 1991. Fans paid $20 for a chance to watch stars like Boyz II Men, Run-DMC, Jodeci, Heavy D, and Big Daddy Kane.

However, the event spiraled out of control as 5,000 attendees, many without tickets, tried to enter a venue designed for only half that number. The stampede resulted in nine fatalities. Diddy faced no criminal charges related to the incident but did lose his position at Uptown Records and was involved in civil lawsuits due to the chaos.

1999: Physical Altercation with Record Executive

Diddy appeared in Nas’ 1999 “Hate Me Now” music video, but soon after questioned a scene that featured him in a compromising position. This led to an altercation with Interscope executive Steve Stoute, whom Diddy reportedly attacked during a meeting.

Stoute later recounted, “One minute I’m in the middle of a meeting, and the next I’m on the floor while Puffy and his crew are kicking and hitting me.”

Diddy eventually pleaded guilty to a minor harassment charge and compensated Stoute with $500,000 for management fees.

1999: Nightclub Shooting Incident

In one of the most serious incidents involving Diddy in 1999, he was at a Manhattan nightclub with then-girlfriend Jennifer Lopez when a dispute arose. Diddy and his bodyguard got into a confrontation with rapper Shyne, leading to a shooting that injured three people, including one who accused Diddy of firing a weapon.

Following police intervention, Diddy, Lopez, and others were arrested briefly, but only Shyne ended up serving nine years for his involvement, which included gun possession charges.

2001: Kim Porter files for child support

Following a lengthy disagreement regarding child support for their son Christian, Diddy came to an agreement with model Kim Porter to pay a reportedly five-figure monthly amount for their child’s educational and medical costs until Christian turned 21.

Diddy is a father to six children from four different women, which include his adopted son Quincy, 33, who is Porter’s child 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 reportedly threatens a business partner

Kirk Burrowes, a former executive at Bad Boy Entertainment, which Combs founded in 1993, filed a lawsuit against him in 2003. Burrowes alleged that Combs had used a baseball bat to coerce him into relinquishing his rights to company stock back in 1996.

In his $25 million lawsuit, Burrowes contended that even after he was fired in 1997, Combs had assured him he would receive a share of the company’s profits. Combs’ legal team dismissed the lawsuit as “pure fantasy,” and it was ultimately dismissed in 2006.

2007: Allegations of assault outside a nightclub

Gerard Rechnitzer filed a lawsuit against Combs in 2007, claiming that after a night out at a Hollywood club, Combs punched him. The confrontation arose when Rechnitzer approached Combs while he was speaking with Rechnitzer’s girlfriend.

A lawyer for Combs labeled the accusation as an attempt by an opportunist to exploit the rapper’s fame. The lawsuit was resolved in 2008 for an undisclosed sum.

2010: Age discrimination lawsuit from a former Bad Boy executive

In 2010, Francesca Spero, a past music executive at Bad Boy Records, filed a $12 million lawsuit against Combs, claiming that he terminated her employment due to her age and a disability. Spero, age 51 at the time, asserted that their working relationship deteriorated after she underwent hip surgery in 2008. The case was settled quietly in 2011.

2015: Altercation with UCLA coach

In 2015, Sal Alosi, a coach at UCLA, accused Combs of attacking him with a kettlebell after he removed Justin Combs, Diddy’s son, from practice. Combs faced several charges, including assault with a deadly weapon, though these felony charges were dropped soon after, as he claimed he was acting in self-defense.

2017: Chef’s lawsuit for sexual harassment

Cindy Rueda, Combs’ former personal chef, sued him for sexual harassment in 2017. She alleged that in two separate incidents in 2015, after receiving criticism from him for being late, she found him in sexual situations while attempting to serve breakfast. She also contended that both he and her other employer made inappropriate comments about her appearance and that she was unfairly compensated for overtime and travel. The lawsuit was settled in 2019 for an undisclosed amount.

2023: Diddy sues Ciroc owner, ends partnership

Diddy’s relationship with liquor giant Diageo took a turn when he filed a lawsuit in 2023, claiming racial discrimination. This came just months ahead of a series of civil suits against him. He alleged that the company failed to deliver on promised investments in the liquor brands Cîroc and DeLeon Tequila, which he co-owned and marketed, respectively. He asserted that he was treated unfairly due to the brands being viewed as secondary “urban” products, alleging that race played a role in restricting distribution to specific areas. Diageo responded by claiming that the relationship deteriorated after Diddy didn’t invest in DeLeon.

Diddy eventually withdrew his lawsuit and cut ties with the company in January.

Current Issues: Sexual assault lawsuits and federal investigation

The latest legal challenges for Combs emerged after his ex-girlfriend Cassie Ventura filed a lawsuit in November, accusing him of rape, sex trafficking, and physical abuse. They reached a settlement the following day for an undisclosed sum. Other lawsuits include allegations from music producer Rodney “Lil Rod” Jones Jr., who claimed Combs was involved in a “sex-trafficking venture.”

Additional lawsuits have been initiated by former model Crystal McKinney, an unnamed 17-year-old girl, former fashion student April Lampros, and former college student Joi Dickerson-Neal. In March, law enforcement conducted raids on Combs’ residences as part of a federal inquiry.

Recently, Dawn Richard, a former member of the group Diddy Dirty Money, filed a lawsuit with 21 counts against Combs, including sexual assault, battery, sex trafficking, and copyright infringement. Combs was subsequently arrested and indicted days later