Sean ‘Diddy’ Combs, a well-known personality in the music industry, recently found himself entangled in a series of legal battles, facing significant charges that might end his career.
The rap mogul, best known for his Bad Boy Records label and countless successful tunes, is currently facing allegations that have shocked many of his followers and the general population.
In the last two years, Combs, 54, has made headlines not only for his business ventures but also for allegations that have cast a shadow over his reputation. The recent developments suggest that his once glamorous life has now taken a darker turn, with the possibility of life in prison looming over him if convicted.
On Tuesday, September 17, federal agents arrested Combs in New York City. The charges against him include racketeering conspiracy, sex trafficking, and transportation for prostitution. The U.S. Attorney’s Office in Manhattan confirmed the arrest information, and it’s clear that this case is being taken very seriously by federal authorities.
If found guilty, Combs may face life in prison, which is a dramatic contrast to the life of luxury and fame he has lived. Despite the extent of the charges, Combs has maintained his innocence, pleading not guilty in federal court shortly after being arrested.
The criminal charge follows multiple civil cases filed in 2023, the most important of which involved accusations made by Cassie, the rapper’s former girlfriend. Cassie’s lawsuit claimed that Combs sexually and physically assaulted her throughout their relationship, adding to his already growing legal woes.

Earlier this year, federal agents from the US Homeland Security raided two of Combs’ houses in Los Angeles and Miami.
The raid carried out on March 25, was part of an ongoing investigation into the claims. Authorities were looking for evidence to back up charges of sex trafficking and other criminal acts involving the musician.
Now it is time we get into the specifics of the timeline of all the allegations against Diddy.
A timeline of allegations and charges Against Sean ‘Diddy’ Combs:
1991 CCNY Tragedy
At City College of New York, Sean Combs co-sponsored a basketball game and concert that ended in tragic circumstances. The event drew a crowd of up to 5,000 people and was hosted in a 2,730-person gym.
Doors had been closed, and people were trying to force their way in. This resulted in a stampede that left 29 people injured and nine dead. Inadequate security was blamed for the accident, and Combs faced multiple lawsuits from the victims’ relatives, which he settled over the years.
1995 Jake Robles Shooting
Serious problems between Combs and Death Row Records co-founder Suge Knight began with a tragic altercation outside an Atlanta nightclub. Jake Robles, a buddy of Suge Knight, was shot during the altercation and subsequently passed away in the hospital.
Even though Combs denied any involvement, his team was frequently held accountable, and Knight supposedly held Combs accountable for the event.
1997 Notorious B.I.G. Murder
The 1997 murder of Biggie Smalls, a.k.a. the Notorious B.I.G., a close friend and partner, was one of the most tragic moments in Sean Combs’ life. The 24-year-old rapper was shot and killed in a drive-by shooting; this incident is connected to the well-known rap industry East Coast-West Coast rivalry.
The murder is still unsolved, but it had an immense impact on Combs, who honored Biggie with the number-one hit song of that year, I’ll Be Missing You, which topped the charts.
Related: Kevin Hart Captured in Sean ‘Diddy’ Combs’ ‘Freak Off’ Party Video Resurfaces
1998 Steve Stoute Assault
When Combs attacked music executive Steve Stoute in 1998, he was taken to court. When Combs’s portrayal of Jesus Christ on the cross was released without his consent, it led to the incident. Combs and two others attacked Stoute in his office out of rage.
Despite Combs’ eventual admitting of guilt and apology, he was charged with assault and told to undergo anger management.
1999 Club New York Shooting
Combs was arrested following an incident at a New York nightclub in which two firearms were discovered in his vehicle after an argument became heated.
Combs and his then-girlfriend Jennifer Lopez were arrested, but he cleared of all counts. This highly publicized case added to the rising number of controversies involving Combs at the time.
2003 Lawsuit by Kirk Burrowes
Sean Combs was sued in 2003 by his former business partner and Bad Boy Entertainment president, Kirk Burrowes. Burrowes said that Combs intimidated him with a baseball bat and forced him to sign away his company shares.
He also claimed that Combs coerced Mary J. Blige into terminating him as her manager. Combs denied the charges, and the case was later dismissed by an appeals court.
2013 Scuffle with J. Cole
In 2013, Combs allegedly got into a fight with rapper J. Cole at an MTV Video Music Awards afterparty.
The argument was believed to have begun following a disagreement over Kendrick Lamar’s verse in the song “Control,” in which Lamar claimed the title of “King of New York.” Although no punches were thrown, the incident sparked public curiosity, with both performers denying that a fight occurred.
2014 Alleged Altercation with Drake
In December 2014, Combs was accused of punching Drake following a dispute outside a Miami nightclub. The argument apparently centered on the rights to a track utilized in Drake’s song 0 to 100.
Though witnesses reported that things became physical, Combs later denied the incident, insisting that Drake was his friend and that nothing major had occurred between them.
2015 Incident with Football Coach
ISean Combs made headlines in 2015 after he had a physical incident with his son’s UCLA football coach. The argument reportedly began during a practice session and escalated when Combs allegedly threatened an intern with a kettlebell.
He was detained and accused with assault with a deadly weapon, but the charges were later thrown out. Combs’ team criticized the media account of the incident as false.
2019 Abuse Allegations by Gina Huynh
In 2019, model Gina Huynh, who had been in an on-and-off relationship with Combs, publicly accused him of physical abuse. In an interview, she said that Combs was abusive towards her throughout their five-year relationship, including an episode in which he allegedly stomped on her tummy.
Huynh also said that Combs offered her money to undergo an abor-tion. Combs did not reply to these allegations, and the story received little media coverage at the time.
16 November 2023: Cassie’s lawsuit
In November, Cassie, who previously dated Sean “Diddy” Combs, caused a stir when she filed a civil lawsuit accusing him of sexual and physical abuse throughout their relationship.
Cassie, whose real name is Casandra Ventura, filed the case on November 16 under New York’s Adult Survivors Act, which allows adult sexual assault victims to make civil claims regardless of when the incident occurred.
Cassie said that Combs raped her, severely abused her during moments of “uncontrollable rage,” and had a “tight grip on her life.” She also claimed that he pressured her into engaging in sexual practices with other men, which he dubbed “Freak Offs,” which frequently involved sex workers he paid to accompany them while he watched.
According to the lawsuit, the assault occurred between 2007 and late 2018, when she left him. Combs vigorously rejected the charges; yet, the two struck a settlement the day after the complaint was filed.
November 23, 2023: Joi Dickerson-Neal Sued Diddy
Shortly after settling the lawsuit with Cassie, Diddy was hit with another sexual assault accusation, this time from Joi Dickerson-Neal, in a lawsuit filed in Manhattan Supreme Court.
According to the lawsuit, Dickerson-Neal alleged that Diddy drugged and raped her while she was a college student at Syracuse University in 1991. She also claimed he recorded the incident and shared it with others in the music industry.
As the New York Adult Survivors Act’s filing window was about to close, Combs denied these new accusations. His spokesperson stated, “This last-minute lawsuit is an example of how a well-meaning law can be misused. Ms. Dickerson’s 32-year-old story is completely false. Mr. Combs never assaulted her.”
November 23, 2023: Third Allegation by Jane Doe
A third lady, Jane Doe, filed a lawsuit accusing Diddy of sexual assault. According to the lawsuit, Diddy and singer Aaron Hall raped her and a companion in New York City more than 30 years ago.
Combs’ spokesman denied these allegations, calling them “fabricated” and implying that they were financially motivated. “Because of Mr. Combs’ fame, he becomes an easy target for these false allegations.”
November 28, 2023: Diddy Steps Down as Revolt Chairman
Following the charges, Diddy resigned from his role as chairman of Revolt, the hip-hop television network he co-founded.
Revolt released a statement stating that while Diddy did not have a day-to-day operational involvement in the network, the decision was made to ensure that the network remained focused on its purpose of supporting Black culture.
December 6, 2023: Another Lawsuit
In early December, a fourth lady filed a lawsuit accusing Diddy of sex trafficking and gang rape.
The lawsuit, filed by a woman under the pseudonym Jane Doe, said that in 1991, former Bad Boy Entertainment CEO Harve Pierre met her in Michigan and persuaded her to fly to Diddy’s recording studio in New York. When she arrived, she was allegedly drugged and gang-raped by Diddy, Pierre, and another person.
That same day, Diddy released a public statement refuting the charges, writing, “ENOUGH IS ENOUGH.” These charges are disgusting and baseless. “I’ll fight for my name and reputation.”
February 26, 2024: Record Producer Files Sexual Assault Lawsuit
In February 2024, Rodney “Lil Rod” Jones, a former producer and videographer for Diddy, filed a lawsuit accusing him of sexual harassment, drugging, and threats. Jones, who worked on Diddy’s Love album, is seeking $30 million in damages.
March 25, 2024: Federal Agents Raid Diddy’s Homes
In March, federal agents raided Diddy’s Los Angeles and Miami properties as part of an ongoing investigation into the sexual trafficking allegations.
A Homeland Security representative confirmed the raids, which followed the allegations of trafficking made in two of the lawsuits.
May 17, 2024: CNN’s Video of Diddy Assaulting Cassie in 2016 Surfaces
In May, a surveillance video was released showing Diddy physically assaulting Cassie during a 2016 altercation. In the video, Diddy is seen chasing Cassie, grabbing her by the neck, and kicking her while she is on the ground.
Cassie’s attorney, Douglas H. Wigdor, commented, “The release of this video only reinforces the disturbing behavior Cassie has courageously brought to light.”
22 May 2024, Crystal McKinney filed a lawsuit.
Crystal McKinney, a model, sued Combs, saying that he drugged her and forced her to have oral sex in 2003.
22 May 2024: April Lampros sued Combs.
Plaintiff April Lampros accuses Combs of sexual assault in a New York complaint filed on Thursday, citing four “terrifying sexual encounters” between 1995 and 2001, including three rapes and one instance of Combs forcing her to ingest ecstasy.
June 2024: Derrick Lee Smith Sues Diddy
Derrick Lee Smith, a 51-year-old prisoner in Michigan’s Earnest C Brooks Correctional Facility who was convicted of first-degree criminal sexual conduct and kidnapping, accused Combs of drugging and sexually assaulting him at a Holiday Inn party in Detroit nearly three decades ago.
On September 9, Smith received a $100 million default judgment as a result of the rapper’s inability to appear in court.
However, Combs’ lawyers tried to overturn the ruling claiming that the statute of limitations for launching the action had expired in 2007 and that the charges lacked credibility. But Sean ‘Diddy’ Combs was Ordered to Pay $100 Million in Sexual Assault Judgment.
July 3, 2023 lawsuit by Adria English
The lawsuit, filed in Manhattan on Wednesday, July 3, 2024, accuses the music mogul of sex trafficking, sexual assault, and a slew of other allegations.
This time, the charges are brought forth by former adult-film star Adria English, who claims Diddy hired her to work as a “go-go dancer” at a party in 2004 before allegedly involving her in more sinister activities.
Adria English asserts that her initial hiring as a go-go dancer was just the beginning of a much darker experience. She alleges that at subsequent parties, her drinks were laced with narcotics, leading to situations where she was coerced into having sex with guests.
However, Sean Combs, who is also known by his stage name Puff Daddy, has categorically denied the accusations.
September 10, 2024: Another Lawsuit by Dawn Richard
Dawn Richard, former member of Danity Kane and Diddy — Dirty Money, filed a lawsuit alleging nearly a decade of sexual and verbal abuse by Diddy. She also claimed that she was owed $3.5 million in unpaid wages and royalties.
Combs’ attorney denied these allegations, claiming they were part of a plan to coincide with Richard’s album release and promotional tour. However, Richard’s former bandmate, Kalenna Harper, expressed a more nuanced view, saying, “While I was present in some of the same situations, many of the claims do not align with my experiences.”
September 16, 2024: Diddy is Arrested and Indicted
Diddy was arrested in mid-September at a Manhattan hotel following the unsealing of an indictment. He was charged with sex trafficking, racketeering, and prostitution-related crimes. Prosecutors accused Diddy of manipulating women into participating in his infamous “freak-offs,” involving narcotics and threats to ensure their compliance.
17 September 2024: Combs denied bail in sex-trafficking and racketeering case
Combs denied bail and ordered to jail as he faces charges of sex trafficking and racketeering. He appears in court in New York and pleads not guilty.
His lawyers tried unsuccessfully to keep him out of jail, requesting his release to home detention, travel restrictions, and a $50m bond in Manhattan court. Prosecutors argue that Combs is “a serious flight risk” and has “the money, manpower, and tools” to flee without detection.
September 24, 2024: Thalia Graves’ Lawsuit
Another lawsuit was filed against the rapper, a few days after his arrest, on September 24th, a woman named Thalia Graves filed alleged the rapper of forcefully raping her in 2001, recording the scenes, and selling them as porn.
According to court documents, Graves said that Combs and his chief of security, Joseph Sherman, brought her to the Bad Boy Records facility in New York City under false pretenses. Graves, then 25, was dating one of Combs’ staffers when the alleged incident occurred.
Graves said she was cornered upon arrival. She further claims that both men gave her a drink that was likely drugged, causing her to briefly lose consciousness. When she woke up, Graves said she found herself bound and restrained, only to be sexually assaulted by both men. As she shouted for help, Sherman allegedly slammed her face down into a pool table. Read Full Article Here.
27th September 2024: Jane Doe’s Lawsuit, Rape & Impregnating Her
On September 27, a Florida woman filed a lawsuit accusing music mogul Sean “Diddy” Combs of drugging, sexually assaulting her, and later getting her pregnant.
The woman, listed as Jane Doe to protect her identity, alleges that Combs not only assaulted her but also intimidated and harassed her in the years following the assaults. She seeks damages for the emotional and physical suffering she endured due to Combs’ actions.
She describes being forced into sexual encounters, which she claims were recorded without her permission by Combs or his associates.
The lawsuit also alleges that Combs drugged her multiple times during these encounters, using alcohol and other unknown substances, including an incident where she unknowingly ingested ketamine at his Los Angeles home in 2022. Read Full Story Here.
October 1, 2024: 120 New Lawsuits
The rapper was hit again on Tuesday, October 1 with over 120 new sexual assault allegations. This was made known by Texas-based attorney Tony Buzbee disclosed during a press conference on Tuesday.
“We will expose the enablers who enabled this conduct behind closed doors. We will pursue this matter no matter who the evidence implicates,” Buzbee said during the press conference. He confirmed his team has “collected pictures, video, texts.”
Buzbee claimed more than 3,000 people have come forward to his office with allegations against Combs, and he wants to file cases in various states within the next 30 days. He also stated that they would name the other defendants at a later date.
According to Buzbee, 62% of this new set of accusers identify as African American and come from more than 25 states, with the majority of which are in New York, California, Georgia, and Florida. Read Full Story Here.