Appellate judges signal strong interest in overturning Diddy’s sentence — but there’s a big catch

During a lively exchange of questions and arguments on Thursday, a trio of federal appeals judges signaled their strong interest in overturning last year’s sentence on prostitution-related charges for Sean “Diddy” Combs.

The appellate judges repeatedly voiced skepticism over the Manhattan sentencing judge’s decision to hold the trial’s ample evidence of coercion and force against Combs in sentencing.

Combs was acquitted of using coercion or force to sex-traffick his two longtime girlfriends, the judges noted — and it’s the appellate court’s duty to ensure that sentencing guidelines are followed, and “that the jury’s acquittal isn’t negated,” as Judge M. Miller Baker noted Thursday.

The judges’ apparent sympathy with arguments by a Combs attorney on Thursday comes with a catch, however.

Even if the defense wins and the case is kicked back down to US District Court Judge Arun Subramanian for resentencing, Subramanian has already said that even without considering coercion and force, 50 months remains, in his judgment, a fair sentence for Combs.

Overturning Combs’ sentence could set an important precedent in future cases — setting firmer guidelines on what federal judges can and cannot weigh at sentencing. Still, resentencing Combs could ultimately result in Subramanian imposing the exact same penalty for the “I’ll Be Missing You” rapper.

“Any potential error would be harmless here,” Christy Slavik, a lead federal prosecutor in the case, told the panel.

‘An exceptionally difficult case’

The millionaire hip-hop mogul was sentenced in October to 50 months in prison on two counts of transporting male escorts across state lines for the so-called “freak offs” at the center of the trial.

In her oral arguments Thursday, Combs defense lawyer Alexandra Shapiro repeatedly told the appellate judges that coercion and force had nothing to do with the jury’s limited finding that Combs transported male escorts across state lines.

“This case presents an important issue about respect for jury verdicts and public confidence in our criminal justice system,” Shapiro told the panel.

In detailed questions and statements from the bench, all three judges at times agreed with Shapiro, suggesting they may be open to Shapiro’s arguments and to vacating the 50-month sentence Subramanian imposed in October.

At other times, the judges of the Manhattan-based US Court of Appeals for the Second Circuit expressed skepticism with both the defense’s and the prosecution’s arguments.

The panel of judges repeatedly interrupted Shapiro and Slavik as they presented their arguments, pressing them hard to defend their positions.

And at least one appellate judge appeared sympathetic to Slavik’s argument that Subramanian correctly weighed Combs’ admitted violence and drug use against him at sentencing.

“We have two women who were plied with drugs to participate in this and one of them became an opioid addict,” Baker told Shapiro at one point, referencing trial testimony by R&B singer Cassie Ventura.

“This is an exceptionally difficult case,” Judge William Nardini said at the hearing’s conclusion, telling both sides that the three-judge appellate panel is reserving decision.

‘A thirteenth juror’

Combs, who was not at the hearing, is currently serving out his sentence at a low-security prison in Fort Dix, New Jersey.

Prison records show the 56-year-old music tycoon is currently expected to be released on April 15, 2028. He has been locked up since his September 2024 arrest.

Thursday’s arguments centered on Combs’ two federal Mann Act convictions, for transporting male escorts across state lines so that he could watch them engage in drug-fueled sex encounters with his two ex-girlfriends, including Ventura.

At Combs’ seven-week trial, the jury cleared the onetime near-billionaire of the top sex trafficking and racketeering conspiracy charges against him. The two Mann Act counts were the only charges the jury found Combs guilty of.

In appellate briefs filed by Combs’ attorneys in December, his lawyers argued that Subramanian “acted as a thirteenth juror.”

“The judge defied the jury’s verdict and found Combs ‘coerced,’ ‘exploited,’ and ‘forced’ his girlfriends to have sex and led a criminal conspiracy,” Combs’ attorneys wrote.

They added, “These judicial findings trumped the verdict and led to the highest sentence ever imposed for any remotely similar defendant — even though most others, unlike Combs, ran prostitution businesses that exploited poor or undocumented women or minors.”