Judge Asks Diddy if Filming Sex Defeats Prostitution Convictions

A Manhattan federal judge questioned Sean “Diddy” Combs’ arguments that his prostitution conviction is unconstitutional as the music mogul’s lawyer said Combs was a producer and consumer of porn entitled to free expression protections.

Is every prosecution for prostitution defeated if the sex is “filmed and watched later?” Judge Arun Subramanian asked Combs attorney Alexandra Shapiro in court on Thursday.

Shapiro said the court wouldn’t need to find that to toss Combs’ conviction. In this case, Shapiro said, the fact that the sex at issue was “highly choreographed” with “role playing” and attention to creating a “sexy” mood should give it the protections of porn.

Shapiro and prosecutors sparred before Subramanian on Thursday as Combs seeks to be cleared of the sole conviction he was left with after trial—transportation for the purpose of prostitution—and leave jail. The arguments stemmed from Combs’ post-verdict motion for an acquittal and the government’s opposing papers.

At the heart of Combs’ post-trial arguments are questions of whether his conviction on the prostitution charges are merited after he was cleared of the more serious charges, trafficking and racketeering. His team says the prostitution charges wouldn’t even have been brought without the more serious charges he was acquitted of.

Prosecutors pushed back on the idea that because Combs filmed his so-called “freak-off” sex parties with escorts, his conviction for transporting escorts to the parties is unconstitutional.

“The act that violated the law was the transportation,” not the filming, assistant US attorney Christy Slavik said.

But Subramanian pushed back on that as well, asking the prosecutor if a movie producer who transports performers to film pornography could be prosecuted under the statute. Slavik said the facts in Combs’ case are “nowhere near that.”

Combs’ team also argued that his conviction under the statute, the Mann Act, isn’t merited because the statute is intended for cases where the defendant made money off of prostitutes or cases involving minors.

Shapiro called the Mann Act “an embarrassment to the United States,” saying it’s historically been applied in a “racist” and “sexist” manner. That’s why, Shapiro argued, Justice Department policy now only advises using it in cases of “pimping” or underage people being paid for sex.

Here, the government was criminalizing a “threesome” among consenting adults, Shapiro argued. “It’s unclear why this should be criminal in 2025" even if “the third individual is paid.”

Shapiro also argued that the statute doesn’t apply to Combs because he didn’t have sex himself with the prostitutes; he just watched and at times filmed.

Subramanian asked if she’d consider it prostitution if hypothetically a businessman paid for a client to have sex at a brothel, where the businessman didn’t have sex with a prostitute himself. Shapiro said she wouldn’t consider that prostitution.

The government defended criminalizing prostitution in general, saying there’s a longstanding history of states doing so to prevent violence against women, drug use, and other “secondary effects.”

The Mann Act’s goal of “thwarting prostitution” holds up under that reasoning and applies here, Slavik said. She also argued that this case involved those secondary effects, saying the evidence showed Combs hit women at his sex parties and used and gave out drugs.

Subramanian told both sides their arguments were “superb” and said he’d rule shortly, ahead of Combs’ Oct. 3 sentencing.

Combs has asked for a 14-month sentence, most of which he’ll have served by his sentencing date. The government hasn’t filed its recommendation yet but indicated they’ll ask for several years.

The case is United States v. Combs, S.D.N.Y., No. 1:24-cr-00542, oral argument 9/25/25.