Diddy’s freedom may hinge on how a panel of three judges interpret what happened between him and Cassie Ventura on a flight in 2012.
On Thursday (April 9), Alexandra Shapiro, the lead appellate attorney for Sean “Diddy” Combs, went head to head in a Manhattan federal courtroom with government prosecutor Christy Slavik in front of a panel of three judges for the Second Circuit Court of Appeals.
Diddy is appealing the 50 month prison sentence handed to him last fall by Judge Arun Subramanian for two counts of violating the Mann Act (transporting someone across state lines for the purposes of prostitution) by arranging “freak-offs” — the sometimes days-long, drug-fueled sexual encounters that Combs would arrange, and often film, between his girlfriends and male escorts.
At the center of Thursday’s argument was the issue of whether Judge Subramanian considered acquitted conduct when sentencing Diddy. Almost all of the mogul’s legal team for his seven-week trial was on hand, including Brian Steel, Marc Agnifilo, and Nicole Westmoreland. Several members of Diddy’s friends and family were also there, though the mogul himself, his mother, and his children were absent.
Alexandra Shapiro’s primary argument was that, because her client was acquitted of sex trafficking charges — and thus the jury didn’t find Diddy guilty of having used force, fraud, or coercion to get Cassie Ventura and the pseudonymous Jane Doe to participate in the freak-offs — Judge Subramanian had erred when he’d added an enhancement for coercion to the mogul’s sentencing guidelines. (More about federal sentencing guidelines and how they work here).
Slavik, for her part, argued that the judge hadn’t considered acquitted conduct at all, but rather conduct that Diddy had admitted to over the course of trial. In addition, she said, Judge Subramanian was clear at sentencing that even if he hadn’t added the enhancement, as well as a separate enhancement for Combs being the leader of a criminal enterprise that involved five or more people, he would still have arrived at the same 50-month sentence.
Much of the argument — originally scheduled for 10 minutes on each side, but ultimately stretching closer to 40 minutes each, with frequent interruptions from all three judges — ended up being about a spring 2012 flight back to New York from the Cannes Film Festival.
Cassie Ventura testified that on that flight, she didn’t want to sit near Diddy, because during the festival, he’d accused her of stealing drugs from him and subsequently been abusive. But he traded seats to be near her and, for the duration of the flight, made Cassie watch videos of freak-offs and threatened to release them. Then, when they arrived back in New York, he demanded a freak-off.
During sentencing, Judge Subramanian said of this conduct, along with a separate incident where Diddy threatened to stop paying Jane Doe’s rent unless she continued participating in freak-offs, “There is no doubt that this evidence counts as coercion.”
Whether he was right about that was an issue the judges, Shapiro, and Slavik spent a lot of time debating.
Shapiro said that because her client had been acquitted of sex trafficking, it was wrong to consider that behavior as coercive, and subsequently wrong to apply a coercion enhancement to the sentencing guidelines.
“The test should be that courts cannot use acquitted conduct for guidelines purposes unless the defendant was also convicted for that conduct,” she said.
And, she continued, because the government relied almost entirely on evidence about the transportation of escorts, not Cassie or Jane, to prove their Mann Act case, there is no convicted conduct that amounts to coercion.
As for Judge Subramanian’s protestation that the enhancements didn’t change his ultimate decision, Shapiro said, “He can’t insulate himself from review just by saying it.”
Christy Slavik fired back, saying that Judge Subramanian had correctly considered Diddy’s conduct, because it applied to both the sex trafficking counts and his violations of the Mann Act. She said that conduct like the Cannes flight “establishes an element of” his Mann Act violation, so it’s fair game for the judge to take into account.
She said that the Cannes flight, as well the Jane Doe incident, “both proved the Mann Act and met the coercion enhancement.” She emphasized that those two incidents were admitted conduct, and thus shouldn’t be considered acquitted.
Judge William Nardini ended the proceedings by proclaiming it “an exceptionally difficult case,” and said the panel would be announcing its judgment via written decision.
Thursday's arguments came after, and reiterated the main points of, hundreds of pages worth of arguments filed over the preceding months. Diddy's initial brief in his appeal, filed in late 2025, argued that Judge Subramanian had acted as a “thirteenth juror,” sentencing the mogul to more time than he deserved by considering acquitted conduct.
Diddy’s team also continued their argument, first advanced months prior, that his behavior at freak-offs was constitutionally protected because he was acting as an amateur pornographer — an argument that did not come up at all on Thursday.
In February of this year, prosecutors fired back with their own brief, which called many of Combs’ arguments “meritless.” They especially objected to the acquitted conduct argument.
"According to [Diddy], the District Court should have closed its eyes to how he carried out his Mann Act offenses and abused his victims—violently beating them, threatening them, lying to them, and plying them with drugs,” prosecutors wrote.
Diddy’s side responded one last time about a month ago, sticking to his amateur pornographer defense.
