Appeals court grills attorneys over whether Sean ‘Diddy’ Combs was improperly sentenced

By Kara Scannell, Nicki Brown, CNN

New York (CNN) — A panel of federal appellate judges on Thursday grilled US prosecutors and lawyers for Sean “Diddy” Combs over the validity of his 50-month prison sentence for his conviction on prostitution-related charges.

Combs’ lawyers are seeking the music mogul’s release from prison, arguing his trial judge improperly considered conduct for which Combs had been found not guilty – namely the evidence linked to the more serious counts of racketeering conspiracy and sex trafficking.

“Their unanimous verdict was not guilty on the most serious charges,” defense attorney Alexandra Shapiro told the Second Circuit Court of Appeals on Thursday. “The jury did not authorize punishment for sex trafficking or conspiracy, but that’s what drove the sentence here.”

Prosecutors, in turn, are asking the appeals court to affirm the conviction and sentence.

Assistant US Attorney Christy Slavik argued Combs’ sentence was based in part on many factors that did not include acquitted conduct, including his history of abusing women.

“What the judge did here, what really drove his analysis, didn’t rely on acquitted conduct,” Slavik said. “It didn’t even rely on disputed issues to begin with.”

The court had set aside 20 minutes for both sides to make their cases. But the hearing lasted roughly two hours as the judges peppered the attorneys with questions about evidence and hypotheticals as they grappled with how to decide the issues.

“This is an exceptionally difficult case,” Judge William Nardini said at the conclusion of the hearing. The panel did not issue a decision Thursday, although Shapiro urged the judges to rule as quickly as possible.

Combs did not attend the arguments.

The founder of Bad Boy Records was convicted last July on two counts of transportation to engage in prostitution in violation of the Mann Act for arranging travel for escorts to engage in sex acts with his then-girlfriends, Cassie Ventura and a woman who testified under the pseudonym “Jane.”

Combs was acquitted of racketeering conspiracy and sex trafficking. Prosecutors alleged Combs coerced the two women into having sex with male escorts, often by supplying drugs to sustain them over multiple days. The marathon sex sessions – which were often filmed – were referred to as “Freak Offs” and “hotel nights.”

Combs was sentenced to more than four years in prison in October. He is currently scheduled for release in April 2028, according to records from the US Bureau of Prisons. He has been held in federal custody since his arrest in September 2024.

Prosecutors say sentence was justified by ‘overlapping conduct’

Combs’ lawyers argued he should be released because defendants convicted of similar prostitution-related offenses typically receive sentences of 15 months. They are also asking the appeals court to acquit Combs of the prostitution-related charges or send the case back to US District Judge Arun Subramanian for resentencing.

At the outset of Thursday’s hearing, Nardini noted the Second Circuit has previously held it was constitutional for a sentencing judge to consider acquitted conduct.

But Shapiro argued the court has not weighed in since the US Sentencing Commission issued guidelines prohibiting acquitted conduct from being considered when calculating advisory sentencing guidelines.

“I don’t think the court has expressly addressed this issue since the guideline amendment,” she said.

Prosecutors said the new guidelines apply when calculating the sentencing range, not determining the sentence. In the latter, judges are allowed to consider other factors, including the character of the defendant.

Shapiro argued prosecutors spent their time at trial trying to prove the more serious charges in the case, and that the Mann Act charges were merely an “afterthought.”

Judge M. Miller Baker suggested Subramanian was “mixing and matching” evidence that was introduced to prove the other charges to support Combs’ sentence.

“Why shouldn’t we hold you to the way you prosecuted the case?” Baker asked prosecutors Thursday. “You went to the jury, and you said this man did all these terrible things for purposes of the RICO conspiracy, for purposes of sex trafficking, and they acquitted him. And then for the Mann Act, it was just a sideshow.”

Slavik argued there was a lot of “overlapping conduct” between the individual charges.

“The evidence of the hotel nights and the Freak Offs related both to the sex trafficking and the Mann Act charges,” Slavik said, adding there was never a “dividing line.”

Shapiro argued the judge sentenced Combs based on instances of coercion, an element of the sex trafficking charges which she argued the jury rejected.

“(Subramanian) found coercion when the … jury had not found coercion,” she said.

Slavik argued that, even if the appeals court disagreed with the trial judge’s findings related to acquitted conduct, the sentence should be affirmed since the trial judge said he would have reached the same sentence.

“(Subramanian) unequivocally and explicitly stated that he would impose the same sentence regardless of the acquitted conduct guideline,” Slavik said.

As an example, Slavik said the judge identified five “criminally liable participants” who were involved in the transportation of the escorts to justify a higher sentence.

Combs’ attorneys also objected to Subramanian’s characterization at sentencing of Ventura, Jane and the escorts as “victims,” which impacted the sentence.

Jurors did not believe Ventura and Jane were victims, Shapiro said, since they acquitted Combs of the sex trafficking charges related to the two women. The escorts should also not be classified as victims, which are defined as people who were “harmed or injured by the offense,” she said.

Amateur pornography argument not a focus of hearing

In court filings, Combs’ attorneys also argued his conviction on prostitution-related charges should be overturned because he engaged in voyeurism and amateur pornography – conduct they say is protected by the First Amendment.

The issue was not a focus of Thursday’s arguments. But Combs’ attorneys say prostitution is not defined in the Mann Act and ask the appeals court to reject an “overbroad interpretation of the statute.”

“Freak-offs and hotel nights were highly choreographed sexual performances involving the use of costumes, role play, and staged lighting, which were filmed so Combs and his girlfriends could watch this amateur pornography later. Pornography production and viewing of this sort is protected by the First Amendment and thus cannot constitutionally be prosecuted,” his lawyers wrote in a court filing.

“In other words, the term ‘prostitution’ in the Act should be limited to those situations where a paying customer engages in sex with the person being paid,” his lawyers wrote.

Prosecutors called Combs’ argument “meritless.”

“Combs is entirely differently situated from adult film distributors: He hired and transported commercial sex workers to have sex with his girlfriends for his own sexual gratification, sometimes directly participating in the sex acts,” prosecutors wrote in a response filed in February.

To side with Combs, prosecutors said, would mean “any defendant who transported others to engage in prostitution could escape liability simply by watching or filming the sex.”

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