Sean 'Diddy' Combs sentenced to 4-plus years over depraved 'freak-off' sex sessions
Published in News & Features
NEW YORK — Disgraced Bad Boy Records founder Sean “Diddy” Combs was sentenced to 50 months in federal prison Friday for transporting women and male escorts across the U.S. for more than a decade to engage in depraved and morbidly relentless sexual performances, so-called “freak-offs,” despite an eleventh-hour apology and plea for mercy.
Manhattan federal court Judge Arun Subramanian handed down the term, which also included a $500,000 fine, after federal prosecutors in the Southern District of New York asked for a substantial term of more than 11 years to reflect Combs’s absence of remorse and “decades of unchecked violence” against women.
The judge said Combs’ claim that escorts were paid for their time and not sex was “flatly inconsistent with reality and any acceptance of responsibility.”
Over the course of several hours in a packed 26th-floor courtroom, the mogul, his attorneys, six of his teenage and adult children, and a reverend effectively begged the judge to let him walk free, with his team describing him as “a civil rights leader” and playing a campaign launch-style 11-minute video.
“I got lost in the excess. I got lost in my ego,” Combs told the judge, also apologizing to his victims. “Because of my decisions I lost my freedom. I lost the opportunity to effectively raise my children and be there for my mother. I lost all my businesses. I lost my career. I totally destroyed my reputation. But most of all I lost my self respect. I been humbled and broken to my core. I hate myself right now. I’ve been stripped down to nothing. I really am truly sorry for it all, no matter what they say.”
In a letter to the judge on the eve of sentencing, Combs said he’d become a new man, mentoring fellow inmates at Brooklyn’s Metropolitan Detention Center, some of whom wrote to the judge, and claimed he’d worked to desegregate the scandal-plagued jail facility.
“I can’t change the past, but I can change the future,” Combs told the judge. “I ask your honor for mercy. I beg your honor for mercy.”
But Assistant U.S. Attorney Christy Slavik, addressing the court Friday, said Combs’ pleas for leniency and claims of rehabilitation were refuted by his brazen assurance, so confident in the likelihood he’d walk that he booked a speaking engagement in Miami next week.
Calling him out “for the height of hubris,” Slavik said, “He doesn’t fully grapple with how his actions got him here — his respect for the law is just lip service.”
The father of seven evaded a potential life sentence when a jury acquitted him on the more serious counts of sex trafficking and racketeering at the conclusion of his seven-week trial on July 2.
His conviction stemmed from allegations that, from 2009 through the summer before his arrest, he had transported and paid dozens of commercial sex workers to sleep with his ex of more than a decade, R&B singer Casandra “Cassie” Ventura, and a woman who testified under the pseudonym “Jane” hundreds of times at dehumanizing, drug-fueled sex sessions in hotel rooms and various properties, during which witnesses said he usually filmed and masturbated.
Ventura, whose four days on the stand contributed to his conviction, had implored Subramanian in a letter to acknowledge evidence of savage beatings he subjected her to for years — stomping on her head, choking her, and leaving her with bust lips and black eyes.
Jurors watched clips of freak-offs and heard sordid details about Combs forcing Ventura to participate when she was menstruating and suffering from chronic urinary tract infections resulting from the sleepless and drug-fueled sessions.
They also saw widely watched footage of Combs violently assaulting Ventura in an L.A. hotel lobby in 2016. The incident, which Ventura said occurred after she sought to leave a freak-off when Combs punched her in the face, was central to the 2023 lawsuit she brought that blasted domestic violence allegations against Combs into public view and sparked the federal probe.
Ventura and Jane each testified that they didn’t want to engage in the sessions, that they had told Combs as such, and that they had suffered in vicious beatings and under threats to their personal and professional reputations, including Combs threatening to release humiliating footage of freak-offs.
Ventura testified about Combs and members of his staff storing weapons in safes and displaying them as “a scare tactic.” The jury also heard allegations from the rapper Scott “Kid Cudi” Mescudi that Combs had sought to kill him, broke into his house and sent men to torch his sports car, that he had threatened an assistant at gunpoint, and raped a different assistant, “Mia,” who pulled out of speaking at the last minute Friday due to the defense’s recent written arguments about her that prosecutors called “bullying.”
Friday’s sentencing caps a precipitous downfall for Combs, long a kingmaker in his industry.
The once high-energy hustling rap impresario born in Harlem rose to fame nurturing ultimately prolific artists who defined the 1990s hip-hop era, including Christopher “The Notorious B.I.G.” Smalls, Mary J. Blige, Faith Evans, 112 and Craig Mack. He played a central role in the notorious East Coast-West Coast rap rivalry that led to the still unsolved killings of Smalls and Tupac Shakur, killed seven months apart in 1997 in drive-by shootings.
Combs broke out from behind the scenes and released his first personal album “No Way Out” under his former stage name “Puff Daddy” the year of Smalls and Shakur’s killings, going on to make hundreds of millions in the coming decades through a combination of Bad Boy record sales, his department store clothing line Sean John, his Revolt Films media company and other ventures. Months before his arrest, Forbes reported he was teetering on billionaire status.
But as his star rose, authorities said his sexual exploitation of women devolved to ever greater depths, and he considered himself untouchable.
In late 2023, Manhattan federal prosecutors and Homeland Security Investigations began investigating allegations that Combs had physically and sexually abused intimate partners, arresting him nearly a year later in September 2024. Upon his arrest, the feds seized thousands of dollars in cash, MDMA and ketamine, a monthslong stock of baby oil and lubricant at his residences, and months later, AR-15s with defaced serial numbers in his bedroom closet.
Trial evidence painted Combs’ rage as uncontrollable. He failed to convince multiple judges to free him on a $50 million bond package after his arrest last year. In refusing to release him after he was acquitted of the top counts, Subramanian cited trial testimony about Combs savagely assaulting Jane months in summer 2024, months after learning he was under investigation.
Lawyer Brian Steel on Friday said Combs had gotten his anger under control. He spoke about the mogul’s challenging childhood after his father was murdered when he was 3 and the resulting trauma that he had endured, telling the judge his personal experiences and year in jail would enable him to “heal” young Black men tangled up in the criminal justice system were he to be freed.
“You could use him, your honor, as a tool,” Steel said. “He needs to repair, not be warehoused.”
Fighting back against the prostitution charges, the mogul’s lawyers had argued in vain that he didn’t pay escorts for sex, but for their time, and that he directed freak-offs in First Amendment-protected expression.
Slavik pushed back on Combs’ efforts to paint freak-offs as consensual on Friday, rehashing trial testimony about Ventura participating in one of the sessions while overdosing on drugs, being beaten by Combs at another of the events while an escort waited outside, and Jane begging Combs in vain to make an escort wear a condom.
“There’s nothing mutual about that,” she said.
The jury also heard allegations that Combs’ staff, like personal assistants, high-ranking managerial employees, security personnel, and travel agents, facilitated his crimes and years of physical abuse, whether through monitoring women sent into hiding until their injuries were no longer visible, bribing hotel staff to destroy evidence of him beating Ventura, setting up travel and accommodation for freak-offs, or supplying drugs.
Jurors did not find that the allegations about Combs’ staff supported charges alleging he operated a RICO conspiracy, nor that Ventura and Jane were trafficked for sex through force, fraud, or coercion, leading to outcry from domestic violence advocates and fears over societal misunderstandings of coercion and consent, harkening back to a pre #MeToo era.
Separate from his criminal matter, Combs has been sued for tens of millions of dollars in more than 100 lawsuits brought by men and women, including allegations of sexual violence and exploitation dating back decades. He denies responsibility.
_____
©2025 New York Daily News. Visit at nydailynews.com. Distributed by Tribune Content Agency, LLC.
Comments