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How Diddy Could Win His Case

The Root has been following Diddy's case closely. Here's an analysis on whether he could walk free.

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Why Black-Owned Businesses Face Bigger Risks in a Global Trade War
Why Black-Owned Businesses Face Bigger Risks in a Global Trade War

In Sean "Diddy" Combs' federal trial on sex trafficking and racketeering charges, prosecutors presented over 30 witnesses and tons of damning evidence to support their argument that the Bad Boy CEO is a larger than life celebrity who abused his power to bend people to his will and fall obedient to his sexual cravings. Meanwhile, the defense argued Combs' toxic relationships, drug abuse and violent tendencies do not compute to running a criminal enterprise.

On one hand, Combs could lose this case if the jury is swayed by the tears of witnesses recounting their trauma or the disturbing footage from the freak offs. On the other side, Combs could be victorious if the jury decides the evidence doesn't sustain a criminal conviction but rather prove he's a flawed, complicated individual as the rapper's attorneys argue.

Let's take a deep dive together examining the case and how well the state made their case...

Meet The Charges

Hip-Hop artist Sean 'Puffy' Combs performing on 'MTV 2 Large' on New Year's Eve in MTV's Times Square studios, 12/31/99. (Photo by Scott Gries/ImageDirect)

Out of the racketeering conspiracy, sex trafficking and interstate transportation to engage in prostitution charges, the ladder is what Combs should be worried about. The statute is defined under the Mann Act which makes it a federal crime to transport people across state lines for the purpose of illegal sexual activity.

While covered up domestic violence may not warrant a racketeering conviction, prosecutors provided an overwhelming amount of evidence that Combs organized for male escorts to be flown to various locations for the purpose of paid sex.

Prosecutors Set The Scene

WASHINGTON, DC - SEPTEMBER 21: Sean "Diddy" Combs speaks during the Congressional Black Caucus Foundation Annual Legislative Conference National Town Hall on September 21, 2023 in Washington, DC. (Photo by Jemal Countess/Getty Images for Congressional Black Caucus Foundation)

Prosecutors argue Combs used his “inner circle” of staff members to help him commit crimes including alleged sex abuse committed against exes Casandra “Cassie” Ventura and "Jane" as well as former assistant "Mia."

The state's attorneys claimed his staff worked to promote Combs' power and guard his reputation by covering up his actions. However, a jury might just interpret this as employees doing their job rather than running a criminal enterprise. Combs' maintained a reputation of being an honorable business man among all the former employees who testified.

Defense Bites Back

NEW YORK, NEW YORK - MAY 12: Marc Agnifilo arrives for the continuation of the jury selection phase of the Sean “Diddy” Combs trial at the Southern District Manhattan Federal court on May 12, 2025 in New York City.Combs has been charged with sex trafficking, racketeering conspiracy, and transporting to engage in prostitution. Combs has been in custody at the Metropolitan Detention Center in Brooklyn New York since his arrest last September and has pleaded not guilty on all charges. (Photo by John Lamparski/Getty Images)

The defense attorneys made a very important point to the jury countering the prosecution's claims: Combs is being charged with running criminal enterprise and sex trafficking, not domestic abuse. While the overwhelming evidence of the rapper’s violence may impression the minds of a juror, the defense did define the difference between a jealous, drug abusing boyfriend and a criminal mastermind.

Combs' attorneys painted him as a complicated person, arguing the case is being built on his troubles in relationships and sexual preferences. 

Cassie's Bombshell Testimony

NEW YORK, NY - MAY 07: Sean "Diddy" Combs and Cassie attends the Heavenly Bodies: Fashion & The Catholic Imagination Costume Institute Gala at The Metropolitan Museum of Art on May 7, 2018 in New York City. (Photo by Neilson Barnard/Getty Images)

Singer Cassie Ventura gave a heartbreaking testimony of her toxic, decade-long relationship with Combs. She explained dozens of instances where Combs exerted his control of her through violent, physical abuse. Ventura said these instances would leave her with visible bruises, forcing her into isolation to protect Combs' image.

She also said for freak offs, he ordered her to hire male escorts to meet them in a hotel room where she would be ordered by Combs to have sex with them while he watched and masturbated. Ventura said she felt “disgusting” and “humiliated” but avoided telling the rapper no in fear of retaliation. To a jury, this could be interpreted as coercion under the sex trafficking statute by Combs' alleged use of violence and intimidation to force Ventura into submission.

Did Everyone Witness Diddy's Abuse?

NEW ORLEANS, LOUISIANA - JULY 07: Dawn Richard speaks during an interview for Day 3 of the 2024 ESSENCE Festival of Culture presented by Coca-Cola at Caesars Superdome on July 07, 2024 in New Orleans, Louisiana. (Photo by Josh Brasted/Getty Images for ESSENCE)

Across testimonies from a variety of people including Bad Boy protégé Dawn Richard and Ventura's former best friend Kerry Morgan, witnesses stated they saw firsthand Combs' abuse toward Ventura. Oftentimes, if they ever sought help from Combs' security guards or assistants, they said no action was taken and the police weren't called. This detail further supported the prosecution's theory about the rapper's staff being an "enterprise" to cover up his alleged actions.

Jane's Heart-Tugging Testimony

REUTERS/Jane Rosenberg

Combs' ex-girlfriend who testified under the pseudonym "Jane" gave a nearly identical testimony on her experience dating Combs as Ventura. She said she was regularly flown out to different locations for the purpose of freak offs which she called "hotel nights." Jane recalled these sexual events practically taking over her life as she was constantly in charge of communicating with escorts and keeping up with the pressure of performing to Combs' liking.

Jane said she also experienced physical abuse as a part of her relationship with Combs but not as often as Ventura experienced it. Jane's reasoning for staying with Combs despite the turmoil was true love, she testified. Her statement may sway a jury in favor of Combs given her love for the rapper influenced her willingness to go back - as well as the fact she was financially dependent on the rapper. However, she also stated Combs would threaten her if she refused his wishes.

Freak Off Details

REUTERS/Jane Rosenberg

There were a few common threads between the accounts of the freak-off sex events Combs would host. The rapper himself or his personal assistants would book hotel rooms under an alias. Testimonies revealed Combs would order the women participating to find the male escorts themselves as well as keep up communication with them sometimes, in exchange for nude photos. Combs would then order the escort and the women to have sex a certain way and sometimes role play scenes.

These details, though graphic, may not compel a jury to believe this equates running a criminal enterprise.

The Ugly Side of Freak Offs

NEW YORK, NY - MAY 01: Cassie and Sean 'P. Diddy' Combs attend "Rei Kawakubo/Comme des Garcons: Art Of The In-Between" Costume Institute Gala at The Metropolitan Museum of Art on May 1, 2017 in New York City. (Photo by John Lamparski/Getty Images)

On the other hand, the dark side of freak offs may swing a jury toward believing there was a level of criminal activity - especially, under the claim that Combs' girlfriends were coerced into it.

Hotel rooms were stocked with drugs, alcohol, baby oil and lubricants, the assistant's testified. However, both Jane and Ventura recalled instances of having to ask for the use of protection which Combs was not a fan of. Both women recalled these sex events to be days long at times, resulting in sleep deprivation and even UTI's - which said they were still expected to perform through. Both admitted to ingesting a number of drugs to numb themselves to the experience, suggesting they didn't want to participate. Ventura stated she would have to come down from the amount of drugs she took by an IV drip.

About The Escorts

LOS ANGELES, CA - FEBRUARY 18: Sean Combs and dancer Cassie attend The 67th NBA All-Star Game: Team LeBron Vs. Team Stephen at Staples Center on February 18, 2018 in Los Angeles, California. (Photo by Allen Berezovsky/Getty Images)

Three male escorts testified on their experiences in the freak-offs. The consistent story between testimonies was that they were paid thousands of dollars both before and after performing in freak offs. They also stated their transportation to various cities would be taken care of and booked by Combs. These statements could only push a jury toward validating the interstate prostitution charge.

Blurred Lines of Consent

REUTERS/Jane Rosenberg

Another thing Combs’ attorneys did right was cast doubt on Ventura’s bombshell testimony. To prosecutors, she felt obligated to participate in Combs’ freak-off sex fantasies. However, defense attorneys continuously had her confirm the times she willingly participated in the events, blurring the line of when consent was withdrawn.

Pulling up text messages of her expressing excitement for the freak-offs as well as admitting on the stand that part-took because she loved Combs is all information a juror will use to decide if these events qualify as a crime.

Kid Cudi's Explosive Testimony

NEW YORK, NEW YORK - MAY 22: Rapper Kid Cudi arrives at the Manhattan Federal Court during the Sean "Diddy" Combs' trial on May 22, 2025 in New York City. Combs, 55, has pleaded not guilty on all counts, which include a racketeering charge alleging the hip-hop pioneer was the leader of a sex crime ring that included drug-fueled sex parties through the use of force, threats and violence (Photo by John Lamparski/Getty Images)

Prosecutors used Cudi's testimony to prove Combs' jealousy was more than what the defense tried to make it seem but a catalyst for criminal activity. Cudi said Ventura was on a break from dating Combs when he got in a relationship with the singer. However, once Combs found out about their relationship, Cudi claimed the rapper broke into his home with the assistance of two staff members, one who was an assistant and claimed she was kidnapped.

The following month, Cudi said his dog watcher called him to let him know his car was on fire. Cudi said it appeared to be “the damage of the Molotov cocktail in his Porsche.” However, the DNA evidence from the scene matched to a woman and not a man. Cudi said when he confronted Combs about the situation afterwards, the rapper acted like he didn't know what he was talking about.

Frightening Accounts from Personal Assistants

NEW YORK, NEW YORK - MAY 27: Ex-assistant Capricorn Clark leaves after testifying in the Sean "Diddy" Combs sex trafficking trial at Manhattan Federal Court on May 27, 2025 in New York City. Combs, 55, has pleaded not guilty on all counts, which include a racketeering charge alleging the hip-hop pioneer was the leader of a sex crime ring that included drug-fueled sex parties through the use of force, threats, and violence. (Photo by Adam Gray/Getty Images)

A woman who testified under the alias "Mia" told the jury she was sexually assaulted multiple times by Combs and also forced to perform oral sex on him. She described herself as "brainwashed" as to why she decided to continue working for him.

Other assistants, mainly men, testified to their experience working endless hours for Combs, setting up freak off rooms and witnessing Combs' abuse toward Ventura. Each assistant was also in charge of fetching drugs for the rapper, which is probably why they were granted immunity for testifying against him.

These testimonies gave insight to Combs' operations, some being random acts of violence against rivals and ex-girlfriends or bizarre power trips like forcing them to undergo lie detector tests and making threats over something he didn't like.

Damning Evidence

Photo: Department of Justice
Photo: Department of Justice

Yes, we saw images of Combs' extensive baby oil collection from inside his hotel rooms to the inside of his mansions. However, the most compelling evidence brought forth by the Feds were the firearms confiscated from Combs' homes which were allegedly used to threaten and intimidate his rivals. Also submitted were horrifying pictures of Ventura's bruises, often open and bloodied.

Finally, as much anticipated, the defense submitted audio and video evidence of Combs' interactions with his ex-girlfriends ranging from arguments to full fledged freak off scenes. Reports noted some jurors growing visibly uncomfortable from the footage, some snatching their headphones off and other wincing. Any reasonable person would be uncomfortable with such graphic content but the jurors' reactions suggest the prosecutors won with trying to convince them the women were coerced into the sexual acts.

Motion for Mistrial

NEW YORK, NEW YORK - APRIL 18: Brian Steel, attorney for Sean 'Diddy' Combs, arrives for a hearing at the Southern District of New York Federal Court on April 18, 2025 in New York City. In a motion filed on Wednesday, attorneys for Combs asked to delay the start of his sex trafficking trial by two months after its scheduled May 5 start date. (Photo by Adam Gray/Getty Images)

Attorneys for Combs filed a motion requesting a mistrial based on “prosecutorial misconduct.” They argued that the prosecutors tried to admit a perjured testimony from Bryana Bongolan, who testified that the rapper dangled her over a 17th-story balcony in a random fit of rage.

The defense said Ventura’s claim that she saw the incident herself was false, citing text evidence where the pop singer says she “found out” about the incident, suggesting she actually wasn’t there. They stated Bongolan’s claims “make no sense and seem to be physically impossible,” citing evidence that proves Combs was not even on the same coast as Bongolan around the time of the alleged incident.

Judge Arun Subramanian was not convinced and dismissed the motion.

Sharp Cross Examination

REUTERS/Jane Rosenberg

Overall, the defense has been sharp in comparing witness testimonies to statements given prior to the Feds, challenging details and memory. For example, former Danity Kane member Dawn Richard was clocked by Combs’ attorneys for not telling prosecutors about a death threat she said she received from Combs prior to taking the stand. Attacking witness credibility is a common default defense strategy.

They also submitted a string of text messages from witnesses showing the moments they appeared to be willing participants in Combs' shenanigans or showed overall care and concern for him despite the monstrous claims of his abuse.

Defense's Weakness

REUTERS/Jane Rosenberg

For starter’s, they openly admitted that their client is guilty of domestic violence. What kind of impression does that give to a jury?

Secondly, the defense asked many questions to witnesses pertaining details of their story that don’t necessarily change the overall conclusion that Combs appeared to have violent tendencies - such as trying to shine a light on Ventura’s jealousy of the rapper dating other women or asking an ex-assistant to confirm that he liked his job despite leaving after witnessing Combs’ alleged violence.

They also didn't appear to address the lack of action from Combs' staff but rather tried to divert the attention on the alleged victim and their power to flee a situation or relationship with Combs.

Enterprise Claims

FORT LAUDERDALE, FLORIDA - JULY 25: Entertainer Puff Daddy looks on prior to the Leagues Cup 2023 match between Inter Miami CF and Atlanta United at DRV PNK Stadium on July 25, 2023 in Fort Lauderdale, Florida. (Photo by Hector Vivas/Getty Images)

Prosecutors have been building the narrative through witness testimony, financial statements and travel records that Combs has an enterprise of people who were complicit in his alleged crimes. The state's attorneys also submitted text messages suggesting the rapper transported escorts across state lines and expressed disgust or disapproval whenever women denied wanting to participate in freak offs.

Both pieces of evidence fuel the prosecution's argument that the alleged victims were coerced into sexual acts and that Combs committed interstate transportation for prostitution. The prosecution closed with loads of text messages support this argument.

Defense's 30-Minute Presentation

REUTERS/Jane Rosenberg

It's not a foreign concept for the defense to keep their presentation short and sweet by utilizing the evidence and witnesses presented by the prosecutors as a way to make their case. However, the defense only used 30 minutes to present their case.

No witnesses were called and Combs confirmed that he decided not to testify on his own behalf. Instead, they submitted a few exhibits and stipulations, pointing out inconsistencies in witness statements. The defense also filed a Rule 29 motion, arguing the prosecution failed to meet their burden of proof and requesting their client be acquitted on all charges.

Closing arguments are scheduled for Thursday, June 26. Then, the jury goes to deliberation.

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