A federal appeals court heard arguments on Thursday that could decide how much longer Sean “Diddy” Combs stays in prison. But from the moment his lawyers opened their case, the three-judge panel wasn’t exactly nodding along.
Thank you for reading this post, don't forget to subscribe!Combs — convicted last year on two counts of transporting women across state lines for prostitution under the federal Mann Act — is currently serving a 50-month sentence at FCI Fort Dix, a low-security federal prison in New Jersey. He didn’t attend Thursday’s hearing at the Second Circuit Court of Appeals in Manhattan. His legal team handled it. And the argument they brought was not a modest one.
The defence’s central claim, according to multiple outlets including ABC News and Rolling Stone, was this: the so-called “freak offs” — allegedly drug-fuelled, multi-day sexual encounters described in graphic detail at trial — were actually a form of expressive conduct. Amateur pornography. Constitutionally protected under the First Amendment. Not prostitution under the Mann Act.
The legal strategy effectively asked the court to redraw the line between criminal sex trafficking and protected personal expression. For a lot of people watching online, that was already enough to generate strong opinions.
The Appeal Argument Nobody Expected
Combs’ defence team made two separate arguments before the panel.
The first was the First Amendment claim — that transporting participants to locations for the alleged sessions should not be criminalised because the acts were allegedly expressive and consensual. Prosecutors fired back in court filings, warning that accepting that reasoning could allow commercial sex operations to argue free speech protections.
The second argument hit closer to sentencing law. His lawyers argued that trial judge Arun Subramanian had improperly inflated the sentence by factoring in conduct Combs was acquitted of — specifically the more serious sex trafficking and racketeering conspiracy charges the jury declined to convict on. Defence attorney Alexandra Shapiro told the panel the sentence needed to be reduced “to ensure that not guilty really means not guilty,” according to Reuters.
The judges didn’t just listen. They pushed back — on both sides.
The Bench Had Questions of Its Own
Judge M. Miller Baker raised what became one of the session’s sharpest exchanges. Addressing the conduct at the core of the case, Baker pointed out that two women were reportedly plied with drugs to participate in the alleged sessions — with one allegedly becoming an opioid addict as a result. “Doesn’t that support the reasonableness of this?” he asked, according to ABC News, referring to the sentence’s severity.
The same judge then turned to prosecutors and questioned whether the judge had gone too far in using acquitted conduct to justify such a heavy term. Baker reportedly called the Mann Act charges “just a sideshow” when framing the broader question — a comment that cut both ways and gave neither side a clean read on where the panel was leaning.
That ambiguity played out across social media in real time. On X, opinions split quickly — with one camp finding the “freak offs as art” legal argument almost surreally audacious, and another pointing out that the underlying question about sentencing on acquitted conduct is a genuinely serious legal issue that goes well beyond this specific case. Legal commentators noted that the panel’s questions didn’t necessarily signal an outcome — appellate judges probe both sides regardless of how they lean.
Still, the session generated the kind of uncomfortable tension that rarely resolves cleanly.
The Bureau of Prisons currently lists Combs’ projected release date as April 15, 2028 — a date that accounts for time served and anticipated good-behaviour credits. If the Second Circuit reduces the sentence or orders a resentencing, that date shifts. If the appeal fails entirely, it stays — or could potentially be extended under certain legal scenarios.
The panel could also overturn the conviction altogether, though legal analysts have flagged that as the least likely of the available outcomes. A ruling is expected within weeks to months. Until then, the argument that may have seemed unthinkable — that federally prosecuted sex crimes were, in fact, a protected form of artistic expression — is now formally in front of a federal court.
What comes next is anyone’s guess. Including, it seems, the judges’.
