Billionaire media mogul Sean Diddy Combs pleaded not guilty to federal racketeering and sex trafficking charges on Tuesday. Correspondingly, he has vehemently denied accusations of violence and sexual abuse that have been lobbed at him over the last several months, even as federal agents raided properties linked to him and a damning video surfaced of him attacking a woman.

Enough is enough, the rapper said in a statement in December.

Sickening allegations have been made against me by individuals looking for a quick payday, he said. Let me be absolutely clear: I did not do any of the awful things being alleged. I will fight for my name, my family and for the truth.

But the accusations got harder to deny on May 17, when CNN published previously unseen footage from 2016 that appears to show Diddy violently assaulting his then-girlfriend, singer-songwriter Cassie Ventura. The disturbing footage corroborated claims she made in a bombshell lawsuit filed against him in November.

The 54-year-old rapper, who has also gone by Puffy or Puff Daddy, settled the lawsuit with Cassie a day after she filed it, but the floodgates were opened. Over the next several months, more accusers filed lawsuits claiming he was violent or sexually abusive. In March, Homeland Security Investigations agents conducted the raids in Los Angeles and the Miami area .

And, on Monday, the media mogul was arrested when a federal indictment was unsealed in New York City.

His arrest, raids and lawsuits, which come amid a broader reckoning in the music industry , add to a long list of legal troubles Diddy has faced over the years.

Heres a timeline of allegations made against Diddy throughout his career.

1996: Diddy Found Guilty Of Threatening Photographer With Gun

Diddy was found guilty of misdemeanor criminal mischief in 1996 for using a gun to threaten a New York Post photographer, NPR reported .

The incident occurred in 1995 as Gary Miller was taking photos of Diddys company cars, according to The New York Times .

Diddy and about 10 of his employees surrounded Miller before they menaced him with a pistol and seized his film, according to the Times, which also reported that Diddy denied the accusation.

April 1999: Record Executive Claims Diddy Beat Him Up During Meeting

Record label executive Steve Stoute accused Diddy and others of assaulting him over a dispute involving a music video with rapper Nas in April 1999, according to The Washington Post .

He punched me in the face, and then he grabbed the phone and bashed me in the head with it, Stoute said in a May 1999 interview with the Los Angeles Times .

One minute Im in the middle of a meeting, he said, and the next minute Im down on the floor and Puffy and his guys are kicking and pounding me. One of them picks up a chair and throws it at me. Then Puffy throws my desk over and they just walk out like nothing happened.

Diddy faced up to seven years behind bars, but Stout reportedly asked the Manhattan district attorney to drop the charges following an apology from Diddy, according to The New York Times . Though the assault charge was dropped, Diddy reportedly pleaded guilty to harassment and was ordered to attend one day of anger management classes, according to NPR .

December 1999: Woman Claims Diddy Shot Her In The Face At NYC Nightclub

Amid a Dec. 27, 1999, shooting at a New York City nightclub, a bullet hit Natania Reuben in her face. Reuben claimed she saw Diddy and a rapper named Shyne holding a gun at the time of the shooting. Despite a jury acquitting Diddy in 2001, Reuben has insisted Diddy is the person who shot her.

I would absolutely, unequivocally like the case reopened. It needs to be reopened, Reuben told NewsNation in March . And the saddest part to me is, had people taken what I said more seriously and listened more intently, 24 years worth of people probably would not have had to suffer.

Shyne served time for the shooting after being convicted of multiple charges, including first-degree assault, reckless endangerment and criminal possession of a weapon. Shyne argued he had fired his gun into the air during the conflict, not at Reuben. Reuben has maintained that Shyne is not responsible for her facial injury.

March 2001: TV Host Says Diddy And His Entourage Attacked Him After An Interview

Roger Mills, host of a celebrity TV show, sued Diddy in March 2001, alleging the media mogul and his entourage attacked him and broke his camera following an interview in 1999, Billboard reported .

When Mills asked Diddy about rumors that he was involved in the 1997 killing of rapper Notorious B.I.G., the interview immediately concluded, according to Billboard.

In February 2004, a jury found Diddy not guilty, according to Today .

March 2007: Partygoer Says Diddy Punched Him And Girlfriend At Los Angeles Nightclub

In a March 2007 lawsuit, a man named Gerard Rechnitzer accused Diddy of punching him and pushing his girlfriend at a February 2007 party at Teddys at the Hollywood Roosevelt Hotel in Los Angeles, according to CBS News . The lawsuit was settled in March 2008, and the terms were not disclosed, according to TMZ .