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From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes

From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes

The Bad Boy Entertainment mogul has had to lawyer up for more than a year now.

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Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Photo: Shareif Ziyadat (Getty Images)

It’s been over a year since the fall of Sean “Diddy” Combs first began. Since his ex-girlfriend filed a lawsuit against him alleging sexual abuse, physical abuse, and other horrific acts, the disgraced Hip-Hop mogul has been catching it from all sides.

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We have a while to go before Diddy is set to stand trial in May 2025, but in the meantime, here is an updated timeline of all the lawsuits, evidence, apologies, and more in the federal case against Combs.

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2 / 20

Cassie Files a Civil Lawsuit

Cassie Files a Civil Lawsuit

Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Photo: Taylor Hill/Getty Images (Getty Images)

In November 2023, Diddy’s former girlfriend, singer Cassie Ventura, filed a civil lawsuit against the disgraced mogul citing physical and sexual abuse, forced sex with male sex workers, and even that Combs blew up Kid Cudi’s car, who was dating Ventura at the time. In less than 24 hours, the case was settled out of court.

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3 / 20

Accusers Start to Come Forward

Accusers Start to Come Forward

Joi Dickerson-Neal pictured with Diddy
Joi Dickerson-Neal pictured with Diddy
Screenshot: YouTube

In the days following Ventura’s case, Joi Dickerson-Neal and an anonymous Jane Doe filed separate suits against the rapper. Dickerson-Neal alleged Diddy drugged and sexually assaulted her in 1991. Doe alleged Diddy and a second man raped her and her friend in 1990 or 1991. Doe also said Diddy physically assaulted her again days later.

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4 / 20

A Fourth Lawsuit

A Fourth Lawsuit

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Photo: MEGA (Getty Images)

In less than a month since Ventura’s lawsuit, a fourth alleged victim came forward accusing Combs of sex trafficking and participating in the gang rape of a 17 year old in 2003.

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5 / 20

Diddy Steps Down From Revolt

Diddy Steps Down From Revolt

Sean “Diddy” Combs speaks onstage during the REVOLT Summit Kickoff Event hosted by Sean “Diddy” Combs, REVOLT, and AT&T at the Kings Theatre on July 24, 2019 in New York City
Sean “Diddy” Combs speaks onstage during the REVOLT Summit Kickoff Event hosted by Sean “Diddy” Combs, REVOLT, and AT&T at the Kings Theatre on July 24, 2019 in New York City
Photo: Johnny Nunez (Getty Images)

In light of the recent allegations against him, Diddy stepped down from his position as chairman of Revolt Media.

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6 / 20

Lil Rod’s $30 Million Lawsuit

Lil Rod’s $30 Million Lawsuit

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Photo: @officiallilrod on Instagram, Shareif Ziyadat (Getty Images)

In February 2024, music producer Lil Rod filed a suit against Combs claiming the rapper encouraged him to have sex with prostitutes, groped his genitals, and didn’t pay him $50,000 for his work on Combs’ 2023 album “The Love Album: Off The Grid.”

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7 / 20

Feds Raid Diddy’s Homes

Feds Raid Diddy’s Homes

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Photo: GIORGIO VIERA (Getty Images)

In March, the world watched as Diddy’s Los Angeles and Miami mansions were both raided by Homeland Security. Here, it was made clear Diddy and these allegations were “part of an ongoing investigation.”

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8 / 20

Lawsuit Against Diddy’s Son

Lawsuit Against Diddy’s Son

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Photo: MARIA ALEJANDRA CARDONA (Getty Images)

In April, a lawsuit against Christian “King” Combs also named Diddy as a co-defendant. The suit alleges Christian sexually assaulted a woman working on a yacht chartered by his father.

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9 / 20

TW// 2016 Leaked Video of Diddy Assaulting Cassie

TW// 2016 Leaked Video of Diddy Assaulting Cassie

Surveillance Video: Diddy Seen Assaulting Cassie Ventura in 2016

In May, CNN obtained footage of Combs repeatedly kicking, dragging, and beating his then girlfriend Cassie in a hotel hallway. Combs alleged took the security footage from the hotel and kept in his house.

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10 / 20

Diddy Apologizes

Diddy Apologizes

Diddy Apologizes For His Actions In Cassie Video, “I Was F’d Up And I Hit Rock Bottom”

Shortly after the video leaked, Diddy took to Instagram to express his sincere apologies to Ventura.

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11 / 20

Howard Cuts Ties With Diddy

Howard Cuts Ties With Diddy

Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Photo: Shareif Ziyadat (Getty Images)

In June, Howard University officially severed all ties with Combs and even snatched back his honorary doctorate degree. The university’s Board of Trustees calls Combs’ behavior “so fundamentally incompatible with Howard University’s core values and beliefs,” also agreed to terminate the scholarship program in his name and return the recent $1 million donation made by the rapper.

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12 / 20

Diddy Returns the Key to New York City

Diddy Returns the Key to New York City

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Photo: Jose Perez/Bauer-Griffin (Getty Images)

The day after Howard cut ties with Diddy, New York Mayor Eric Adams asked Combs returns a key to the city in a set of formal letter to Combs rescinding the honor Diddy was awarded the key in 2023.

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13 / 20

Derrick Lee Cardello-Smith Wins Lawsuit

Derrick Lee Cardello-Smith Wins Lawsuit

Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Screenshot: YouTube

In June, a Detroit inmate filed a lawsuit accusing Combs of sexual assault. Initially, a judge ordered Combs to pay Derrick Lee Cardello-Smith $100 million. However, the ruling was reversed after Combs’ representation argues Cardello-Smith failed to prove he served his lawsuit effectively to the rap mogul.

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14 / 20

Dawn Richard Sues Diddy

Dawn Richard Sues Diddy

Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Photo: Jason LaVeris (Getty Images)

Right before Diddy was arrested in September, singer Dawn Richard filed a lawsuit against him citing years of psychological and physical abuse, including groping. She also alleged she witnessed Combs physically assault Cassie Ventura.

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15 / 20

Diddy gets Arrested

Diddy gets Arrested

New surveillance video shows Sean ‘Diddy’ Combs’ arrest

In September, Combs was taken in to custody in the lobby of the Park Hyatt hotel in Manhattan by Homeland Security Investigations.

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16 / 20

Charges Against Diddy Announced

Charges Against Diddy Announced

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Photo: Prince Williams (Getty Images)

Soon after his arrest, Diddy was federally charged with racketeering, sex trafficking and transportation to engage in prostitution. If found guilty, Diddy could be spending the rest of his life behind bars.

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17 / 20

Thalia Graves Lawsuit

Thalia Graves Lawsuit

Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Photo: Frederic J. Brown (Getty Images)

Shortly after Diddy’s arrest, The Root reported Thalia Graves alleged she was lured into meeting Combs and his bodyguard, Joseph Sherman, privately back in 2001. She then alleged she was drugged with a laced drink and “brutally” sexually abused by the two men. The suit also claims a video recording of the assault was shared among a number of people.

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18 / 20

Diddy’s Jail Cell Gets Raided

Diddy’s Jail Cell Gets Raided

Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Photo: Doug Peters (Getty Images)
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19 / 20

Attempting Bail... Again

Attempting Bail... Again

Image for article titled From Cassie to Jail Raids, a Timeline of Diddy's Legal Woes
Photo: Jane Rosenberg (Reuters)

Just ahead of the holiday season, Diddy is attempting to get bail for the third time. If Combs is released, this means he’ll be spending the holiday season with his family. According to his lawyers, Diddy is set to stay in a three-bedroom Manhattan apartment until his trial begins next year.

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