Sean “Diddy” Combs, one of hip-hop’s most powerful and influential figures, was arrested on March 25, 2025, in Miami, Florida, following a federal investigation that had been quietly building behind the scenes for over a year. The arrest came after Homeland Security agents executed coordinated raids on two of Combs’ properties in Los Angeles and Miami, seizing electronic devices, documents, and surveillance footage. These raids were part of a broader criminal probe into allegations of sex trafficking, coercion, drug distribution, and racketeering linked to Combs and his inner circle.
The charges stem largely from a wave of civil lawsuits filed throughout 2023 and 2024 by multiple women, including his former girlfriend and singer Cassie Ventura. Her lawsuit, filed in late 2023 and settled within 24 hours, accused Combs of physical abuse, rape, and forcing her into sex acts with others. Though the case was closed quickly, it opened the floodgates for additional plaintiffs, several of whom described similar patterns of manipulation, threats, and exploitation. While Combs publicly denied all accusations and labeled them “blackmail,” the Department of Justice began its own inquiry, culminating in his high-profile arrest this year.
Before his legal troubles escalated, Combs built an empire as the founder of Bad Boy Records and was instrumental in launching the careers of artists like The Notorious B.I.G., Faith Evans, and Mase. He later expanded into fashion, liquor, and television, becoming a billionaire brand in his own right. But despite his success, Combs’ public image has long been dogged by allegations of violence, workplace misconduct, and controlling behavior behind the scenes.
The current trial is not only the culmination of years of whispered rumors and legal accusations, it represents a potential turning point for the music industry’s reckoning with abuse, power, and accountability. What began as civil lawsuits has now evolved into one of the most significant federal celebrity criminal cases in recent memory.
Week-By-Week Breakdown of the First Two Weeks of the Diddy Trial
The highly publicized federal trial of Sean “Diddy” Combs has been unfolding in New York with intense scrutiny. After months of speculation and multiple civil lawsuits, the criminal proceedings have entered their second month. Here’s a detailed breakdown of everything that took place during the first two weeks in court, outlining each witness, key moments, and how the prosecution is building its case.
Week One: May 12 to May 16, 2025
The week began with the completion of jury selection. Opening statements laid out a clear division between the prosecution, which painted Combs as the orchestrator of a long-running sex trafficking and abuse ring under the protection of his entertainment empire, and the defense, which acknowledged past temper issues but claimed all relationships were consensual and that many allegations were financially motivated.
Cassie Ventura, the central figure in the original 2023 lawsuit that launched the investigation, took the stand on May 13 and remained there for four consecutive days. She testified about years of psychological manipulation, physical assaults, and forced participation in what she described as drug-fueled sex sessions known as “freak-offs.” Her detailed testimony described everything from being isolated and financially controlled to suffering bruises, threats, and mental breakdowns. On the fourth day, she concluded her testimony by addressing a 2016 assault caught on hotel surveillance footage, which was played for the jury and corroborated by additional witnesses.
Week Two: May 19 to May 23, 2025
The second week shifted focus from Cassie to supporting witnesses who either observed the abuse firsthand or were directly involved.
On May 19, a hotel security guard testified that he witnessed the aftermath of the 2016 assault involving Ventura and that he was offered money to suppress surveillance footage. The following day, a male escort detailed an incident where he allegedly saw Combs drag Ventura by her hair and assault her with a bottle during one of the “freak-off” sessions.
On May 21, a woman identified as “Mia,” a former assistant to Combs, began her testimony. She described being emotionally broken down, sexually abused, and forced to assist with logistics of Combs’ alleged abusive behavior. Her emotional breakdown on the stand delayed cross-examination until the next day.
On May 22, rapper Kid Cudi testified that his romantic involvement with Cassie led to direct threats from Combs. He confirmed that his car was firebombed shortly after their relationship became public, something he believed was an act of retaliation. He also recalled Cassie confiding in him about physical abuse.
On May 23, the court heard from multiple former employees including stylists and other assistants. They described what they witnessed while working for Combs, including being asked to clean up after parties involving drugs and sex workers. Several shared that they lived in fear of retaliation and were often coerced into staying silent.
Emerging Themes and Trial Outlook
The prosecution’s case is clear: they are portraying Sean Combs as the head of a highly organized and sustained operation involving sexual exploitation, physical abuse, coercion, and intimidation. They are using the RICO statute to frame these acts not as isolated events but as part of a broader criminal enterprise.
The defense has focused on painting the relationships as consensual, pointing out contradictions between past public statements and current testimony. They have emphasized messages, photos, and other digital communications that suggest continued voluntary contact long after the alleged abuse began.
As of the end of the second week, over sixteen witnesses have testified. The testimony has been graphic, emotionally intense, and at times shocking. The court has already denied one motion for mistrial and the defense is expected to renew its challenges as more testimony unfolds.
While Combs himself has remained silent, his courtroom behavior has drawn attention. On more than one occasion, the judge has warned him to stop attempting to intimidate witnesses through facial expressions and gestures.
The trial is expected to continue for several more weeks. What remains to be seen is whether the prosecution’s case can hold up against cross-examination and whether the defense will be able to dismantle the credibility of the central witnesses. For now, the case remains one of the most closely watched celebrity trials of the decade.
