A closer look at the federal investigation into Sean ‘Diddy’ Combs

By Lisa Respers France, Josh Campbell and Elizabeth Wagmeister

(CNN) — Months after singer Cassie Ventura filed suit against her ex-boyfriend Sean “Diddy” Combs, his life looks very different.

The man who rose from an intern at a record label to building his own music empire in Bad Boy Records, was once a beloved figure who held enough influence to launch recording careers, successful fashion and spirits lines, and even a voting movement.

Those days seem over.

In her now-settled claim filed in November, Ventura accused Combs of raping her in 2018 and years of abuse over the course of their relationship. In the past six months, he has been named in seven other lawsuits in which he has been accused of sexual misconduct and other illegal activity. Combs has vehemently denied claims from many of the civil suits but has not responded to all of the allegations.

After CNN published a 2016 surveillance video that showed Combs physically assaulting Ventura, the Los Angeles County District Attorney’s Office said the incident they described as “extremely disturbing” was outside the statute of limitations to prosecute.

But the video could become evidence in an ongoing federal investigation related to Combs and allegations of sex trafficking. CNN has learned that investigators are preparing to bring accusers of Combs before a federal grand jury in New York, according to two sources familiar with the probe.

This signals that the US Justice Department is moving toward potentially seeking an indictment of Combs. Authorities are “digging deeper” into the civil suits and mining them for potential witnesses and evidence against the star, one of the sources told CNN.

Federal investigators are also looking into allegations of money laundering and illegal drugs, CNN has learned.

“It’s much bigger than just these lawsuits,” one of the sources familiar with the scope of the investigation said.

Here’s a closer look at what has been revealed about the federal case so far.

The searches

Authorities searched Combs’ homes in Miami and Los Angeles on March 25, because he is a target of a federal probe carried out by Homeland Security Investigations (HSI), the lead investigative arm of the US Department of Homeland Security, according to a senior federal law enforcement official briefed on the case. The investigation stems from many of the same sexual assault allegations put forth in the civil lawsuits, according to a second law enforcement source familiar with the searches.

HSI is responsible for investigating transnational crime and threats, including human trafficking, terrorism, narcotics smuggling and other organized criminal activity.

A spokesperson for HSI declined to comment on the existence of a grand jury, but noted the investigation remains ongoing.

A lawyer for Combs objected to how the searches were conducted.

“There was a gross overuse of military-level force as search warrants were executed at Mr. Combs’ residences,” Aaron Dyer, Combs’ attorney, said in a statement to CNN at the time. “There is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated.”

Two of Combs’ adult sons, Justin, 30, and Christian, 26, were detained and briefly handcuffed during the search warrant execution at his Los Angeles mansion. They were not arrested or charged.

Justin’s mother, stylist Misa Hylton, also took exception to how her son and his brother were treated.

“The overzealous and overtly militarized force used against my sons Justin and Christian is deplorable,” she wrote in a social media post in April. “If these were the sons of a non-Black celebrity, they would not have been handled with the same aggression. The attempt to humiliate and terrorize these innocent young BLACK MEN is despicable!”

Hylton is not Christian Combs biological mother. He is the son of the late Kim Porter with whom Sean Combs also shared now 17-year old twin daughters, D’Lila and Jessie.

Potential evidence

The raids on Combs’ homes came weeks after a lawsuit filed against him by Rodney “Lil Rod” Jones, a former producer and videographer for the music mogul. Jones accuses Combs and others of racketeering, sexual assault and sex trafficking in 2022 and 2023 as Jones worked on Combs’ most recent album “Love.” Jones also alleges Combs did not compensate him for his music producing work.

Ventura, too, accused Combs of sex trafficking, allegedly forcing her to engage in various sex acts with male sex workers through threats of violence.

“A decision to settle a lawsuit, especially in 2023, is in no way an admission of wrongdoing,” Ben Brafman, an attorney for Combs, said when Ventura’s lawsuit was settled.

Another attorney for Combs denied Jones’ allegations and called his claims “lies.”

“His reckless name-dropping about events that are pure fiction and simply did not happen is nothing more than a transparent attempt to garner headlines. We have overwhelming, indisputable proof that his claims are complete lies,” attorney Shawn Holley told CNN when the lawsuit was filed.

Authorities searching during raids are usually seeking evidence to confirm that laws have been broken. Examples of what is often seized include computers, cell phones and documents. Both Jones and Ventura claimed video evidence exists of some of the alleged crimes.

Potential video evidence is center stage at the moment as a source has told CNN that federal agents are in possession of video taken inside of Combs’ recently searched residences. It’s unclear whether the video was seized during the raids, or whether investigators obtained video from individuals they have been questioning.

“They are contacting people that they’ve found on the tapes,” a source told CNN.

At least one male sex worker, who claims he has been victimized by Combs, has been questioned during the investigation, one source said. The source added that this individual was seen in footage that is in possession of the federal investigators.

Building a “bulletproof” case

While no federal criminal charges have been filed against Combs, law enforcement sources indicated the Justice Department’s successful efforts to prosecute disgraced R&B singer R. Kelly in 2022 could serve as a model for the current sex trafficking investigation of Combs, depending on what evidence is discovered.

In the case involving Kelly, federal agents with HSI secured a conviction on federal racketeering and sex trafficking charges stemming from Kelly’s efforts over years to use his fame to ensnare victims he sexually abused.

The federal Racketeer Influenced and Corrupt Organizations Act – also known as RICO – is a statute that targets so-called criminal enterprises, and provides for steep penalties that can also be a point of leverage for prosecutors wishing to flip potential co-conspirators or encourage defendants to take plea deals.

There is no known timeline for possible federal charges against Combs, however, approaching his sex trafficking investigation as an effort to illuminate a criminal enterprise involving others would require a more robust effort by federal agents to prove the elements of any conspiracy.

“When prosecutors charge RICO, they have to prove more to make their case – that a criminal enterprise exists, that the defendant was a member of it, and that the crimes are related to that enterprise,” said Elie Honig, CNN Senior Legal Analyst and former federal prosecutor. “But it also gives prosecutors a powerful tool to take down large criminal operations.”

One source told CNN investigators are being thorough and taking their time to ensure that an indictment, should there be one, is “bulletproof.”

CNN’s Sandra Gonzalez, John Miller, Elizabeth Wolfe, Eric Levenson, Denise Royal, Holmes Lybrand and Carlos Suarez contributed to this report.

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