Sean 'Diddy' Combs has had history of legal troubles

On Monday, the Los Angeles home of Sean "Diddy" Combs was raided by Homeland Security Monday in connection with a federal sex trafficking investigation, officials said, according to FOX 11 Los Angeles. 

But it's not the first time the musician crossed paths with law enforcement and the judicial system.

Diddy accused by male music producer of sexual assault in 2024

In February, music producer Rodney "Lil Rod" Jones Jr. filed a lawsuit against Combs, accusing the rapper of sexually assaulting him and forcing him to perform sex acts with prostitutes, in documents obtained by Fox News Digital.

Jones, a producer on Combs' latest studio album, "The Love Album: Off the Grid," lived with Combs for extended periods of time, according to the documents. He accused Combs of unsolicited groping and sexual touching of his anus on multiple occasions and also described several scenarios of inappropriate work conditions.

Combs' lawyer disputed the claims, calling them "pure fiction" in a statement shared with Fox News Digital.

Diddy sued by ex-girlfriend over rape, abuse allegations in 2023

Last year, Diddy's ex-girlfriend, Cassie, sued the musician over allegations of rape and abuse, Fox News Digital confirmed. Cassie, legally known as Casandra Ventura, alleged she endured "over a decade" of Diddy's "violent behavior and disturbed demands" in a lawsuit filed in New York federal court.

"After years in silence and darkness, I am finally ready to tell my story, and to speak up on behalf of myself and for the benefit of other women who face violence and abuse in their relationships," she told Fox News Digital in a statement. "With the expiration of New York’s Adult Survivors Act fast approaching, it became clear that this was an opportunity to speak up about the trauma I have experienced and that I will be recovering from for the rest of my life."


LONDON, ENGLAND - NOVEMBER 07: Diddy performs at O2 Shepherd's Bush Empire in a special one night only event at O2 Shepherd's Bush Empire on November 07, 2023 in London, England. (Photo by Samir Hussein/Getty Images for Sean Diddy Combs)

Cassie specifically accused Diddy of raping her in her own home and forcing her to have sex with male prostitutes while he watched and filmed. The R&B singer also alleged Diddy "punched, beat, kicked and stomped" on her.

A lawyer for the rapper denied Cassie's claims.

One day after shocking allegations, the two settled the lawsuit.

Diddy sued by ex-chef for sexual harassment and retaliation in 2017

According to the Hollywood Reporter, in 2017, Diddy was sued by his former chef, Cindy Rueda, for sexual harassment, retaliation, defamation, failure to pay overtime and intentional infliction of emotional distress, among other claims. Local outlets reported that the lawsuit was settled for an undisclosed amount in February 2019. 

Diddy's arrested for assault, charge later dropped in 2015

Variety reported in 2015, charges were dropped against Diddy after he was accused of assaulting a UCLA football coach. Combs was arrested for allegedly swinging a kettlebell at an assistant coach, leaving him to be charged with assault with a deadly weapon.

Puff Daddy arrested along with Jennifer Lopez in 1999

In December 1999, Combs and Jennifer Lopez were arrested in New York City for criminal possession of a weapon and possession of stolen property.

The arrests occurred shortly after a shooting took place at a club in the area, according to MTV.

Lopez was detained by authorities for 14 hours and was even handcuffed to a bench in a Midtown Manhattan police precinct, The New York Daily News reported at the time. Police released the singer in the late afternoon.

Combs was charged with illegal possession of a weapon, but was later acquitted.

Puff Daddy tied to deadly stampede at 1992 event

In 1992, several people were killed and injured during a celebrity basketball game in Harlem, New York. Diddy was one of the promoters of the event. No charges were filed against Diddy. 

RELATED: Diddy's LA home raided by Homeland Security

FOX News contributed to this report. This story was reported from Los Angeles.