VIPs Like P. Diddy Don’t Just End Up in Court. Their Words Help Get Them There.

Sean “Diddy” Combs, once a star of the hip-hop world, is now in the spotlight for facing some of the most serious federal charges imaginable: racketeering, sex trafficking, kidnapping, forced labor, obstruction of justice, arson, and more. According to the indictment now unfolding in U.S. District Court in New York, Combs didn’t act alone — prosecutors say he operated a criminal enterprise for over 20 years, using his business empire and inner circle to carry out and conceal abuse.

The charges read like a dystopian screenplay: sex acts filmed without consent, hush money delivered by employees, sex workers flown across state lines for parties called “freak offs,” and a culture of silence maintained through loyalty, threats, and financial control. Among the evidence: thousands of bottles of baby oil used in the sex parties, seized by federal agents.

At the center of the case is Combs’s abusive relationship with recording artist Cassandra “Cassie” Ventura, who was signed to a 10-album deal with Bad Boy Records. She testified she was coerced into a humiliating, drug-filled relationship with Combs — a man 20 years her senior — because he controlled her career. In a 2023 lawsuit, Ventura said Combs raped her, forced her to have sex with male prostitutes while he watched, and beat her repeatedly. In 2016, in a Los Angeles hotel hallway, he kicked, hit, and dragged her, an incident captured in a 15-minute surveillance video and played in the courtroom last week. Ventura said she stayed in the relationship out of fear for her reputation and her life. Combs’ defense, however, has begun to portray her as a willing participant who sent texts including, “I’m a very lucky woman. I miss you so much. I’d fly wherever you need me, whenever. I love you.” 

But she also sent texts to Combs after alleged assaults, writing: “I have a black eye and a fat lip,” and explaining she had to show up to a public event that way. Her lawsuit was quickly settled, with Combs not admitting guilt, but it became the foundation for the federal indictment. Ventura is just one of several witnesses testifying about the sex trafficking in the trial, which is expected to last six to eight weeks and is being covered globally. 

Most companies will never face a case like this. But the dynamics that allowed it — unchecked power, silence, complicity, a paper trail — exist in workplaces everywhere. VIPs like P. Diddy don’t just end up in court. Their words help get them there.

At Alphy, we’re not investigating celebrity sex crimes. We don’t monitor private chats or encrypted apps. But our HarmCheck.ai does analyze email in real-time, and can record communication from various chat platforms. That’s where harm often begins. Before the lawsuit. Before the FBI. Before the front-page news.

The indictment shows how Combs’s employees — security, assistants, household staff, senior supervisors — allegedly enabled a system of abuse. They arranged travel. They stocked hotel rooms. They watched. They stayed silent. And most importantly, they communicated. The indictment is relying heavily on captured communication.

The logistics aren’t fully spelled out in the indictment, but the pattern is clear. Travel booked. Hotel rooms reserved. Supplies delivered. “Recovery” treatments scheduled. In email, these kinds of messages usually look routine, and HarmCheck wouldn’t necessarily flag them.

But when harm is happening behind the scenes, it often leaks into communication. 

The warning signs often look like this:

• A degrading message brushed off as a joke.

• A retaliatory email that no one flags.

• A physical threat. 

HarmCheck flags that kind of language in real time and compiles it to help risk managers see where harmful behavior may be surfacing. You won’t see a pattern of hotel bookings. But you will see a pattern of intimidation, sexual harassment, or bias, and where it’s coming from, before it turns into a lawsuit or scandal.

The consequences for Combs could go far beyond prison. If convicted, the government may seize assets tied to his business empire — from record labels to media companies — under laws allowing forfeiture of anything used to commit racketeering or sex trafficking. Forbes estimated his wealth at $400 million in 2024. 

Reputational and legal risk often go hand in hand. And that risk can become very expensive. At Alphy, we’re not here to moralize. We’re here to help companies detect danger before it detonates. Powerful people rarely fall alone — and their words often help take them down. 

No one starts with racketeering. They start with a message.

Book a free demo with HarmCheck today: http://harmcheck.ai/demo

Carolyne Zinko is the editorial director and AI editor at Alphy.

HarmCheck by Alphy is an AI communication compliance solution that detects and flags language that is harmful, unlawful, and unethical in digital communication. Alphy was founded to reduce the risk of litigation from harmful and discriminatory communication while helping employees communicate more effectively. For more information: www.harmcheck.ai.