Decoding Diddy’s Expected Legal Strategy

Sean "Diddy" Combs’ criminal case will stretch on through a good chunk of 2025. His trial is currently scheduled to start next May, though that may be delayed if new charges or defendants are introduced. But even though we’re still months away, a close look at the paperwork that’s been filed so far—and what the mogul’s legal team has been saying— reveals that his attorneys have dropped serious hints about what his defense might look like.

What Diddy's lawyers are asking for

On October 15, Diddy’s attorneys filed a letter motion to Judge Arun Subramanian and included an accompanying exhibit. The main focus of the letter was to request that the government identify alleged victims’ names—but that’s not what was interesting about it. Buried on pages three and four of the exhibit is the motherlode: a list of the types of “exculpatory material” that Diddy’s team wants from the government—in essence, Diddy’s lawyers are telling prosecutors, if you have anything like this, turn it over to us.

Of course, the government has to turn over all of its potentially exculpatory evidence. So it’s notable that Diddy’s team lays out the specific types of evidence it’s looking for—a clue that these may be defenses they’re thinking about presenting.

The list of types of material can be grouped into a few categories. One relates to whether participation in Diddy’s now-notorious “Freak Offs” was voluntary. In fact, the very first point requests “All information indicating that participation in the ‘Freak Offs’ was consensual” and that people were not “forced” to take part. This section also takes aim at the narrative that has taken shape in many of Diddy’s civil suits: that alleged victims were forced to consume alcohol that was laced with the date rape drug GHB. Diddy’s team asks for any info showing “to the extent any participants consumed drugs or alcohol, they did so voluntarily.”

Another category is aimed at the credibility of any alleged victims: whether they are “lying, exaggerating, or are otherwise unreliable, including all information relating to the alleged victims’ financial, reputational, personal, or professional motivations to claim abuse.” Relatedly, Diddy’s lawyers are asking for any hint “showing that, prior to the alleged victims’ motivation to lie, they were not afraid of Mr. Combs, and never reported…any instances of coercion, force, or abuse.” There is also plenty of talk about alleged victims’ “phone records, email records, travel records, arrest records, medical records, drug abuse and rehabilitation records, draft memoirs, financial records, and attempts to commit extortion.”

There are several points that seem aimed directly at the Cassie Ventura video, including suggesting that any disputes between Diddy and alleged victims were “related to infidelity or other interpersonal matters, and not related to alleged force or coercion to participate in a sexual activity”—which matches up with the ways Diddy’s lawyers have spoken about the video in court hearings.

Finally, there’s one that asks for information indicating that the decision to prosecute Diddy was “racially motivated”—something that attorney Marc Agnifilo said to TMZ, and a suggestion that government prosecutors vehemently objected to at a court hearing earlier this month.

What a lawyer says about Diddy's gameplan

These seem like attempts to paint alleged victims as unreliable or out for money; to portray the Cassie video as a fight between a troubled couple; to demonstrate that any sexual activity was consensual; and to say that the feds brought the case in the first place because of Diddy’s race.

But is that really what Diddy’s lawyers are up to? Have they given up their whole defense in document 36-1?

“It's a game plan. And I do think it's a reasonable, likely game plan,” says attorney John M. Phillips. Phillips, a Florida-based lawyer, has no relation to Diddy’s situation, but he’s been involved in plenty of high-profile cases of his own: he’s repped Omarosa Manigault Newman in her battle against the Donald Trump campaign; been in the corner of “Tiger King” Joe Exotic; and taken part in a case probably familiar to Complex readers—representing the family of one of YNW Melly’s alleged victims in a civil suit. Complex asked him to take a look at Diddy’s list.

“They're asking for specific things that would support their case,” he said. “So you can see, reading between the lines of what they're asking for, how that could be their defense.”

He notes that Diddy’s lawyers are really fighting three battles at once: the criminal case, an ever-increasing number of civil lawsuits, and a battle in the court of public opinion.

“So to ask for stuff that paints your narrative serves all three,” he said. “You're asking for exculpatory evidence under the criminal case; but you're also saying, ‘Hey, wait, hold on, court of public opinion. There's two sides to this story, and my client hasn't been convicted yet,’ which is a savvy, media-friendly lawyer’s way to couch this.”

“It's a smart list,” he said. “We can not like it. We can say it belittles victims. But that's literally their job, is to create reasonable doubt.”

Diddy's legal team pushing buttons

Victoria Bekiempis is a journalist who has covered some of the biggest court cases of the last 10 years, featuring figures like Harvey Weinstein, R. Kelly, and Ghislane Maxwell. After viewing Diddy’s list, she tells Complex that she’s seen this movie before.

“Diddy's attorneys are doing what one would expect, and often see, in high profile sex crimes trials,” she said. “Oftentimes, the defense will argue that other factors are motivating their clients' prosecution. For example, attributing prosecution to racism.”

But, she cautions, Diddy’s strategy may not hold up to scrutiny from the judge.

“There is a very big [difference] between what an attorney can say in pretrial filings and what they can say at an actual trial. It's unclear at this time just how much latitude the judge will allow. One might expect to see at least some of this in opening and closing arguments but judges have broad discretion on this point.”

Both Phillips and Bekiempis have thoughts about the “racially motivated” aspect of the list. When I mention to Phillips that the suggestion the prosecution might be because of Diddy’s race really pushed the government’s buttons, he responds that, from a defendant’s perspective, some button-pushing might be a good thing.

“I mean, sometimes you want to push buttons just because it works,” he says. “There's the old joke in law school: if you know the law, argue the law; if you know the facts, argue the facts; if you don't know, just argue. They know the law and they know the facts, but [sometimes] just arguing, if it's working, takes up oxygen in the opposing attorney's room, so you do it—within the confines of ethics.”

And, Phillips argues, it’s not like the suggestion was crazy.

“You can compare it to other cases and other allegations and they're certainly handling Sean's case differently,” he says, noting at the same time that it’s also “also a different kind of case” from something like the Jeffrey Epstein trial.

The Florida attorney also says that “the justice system in and of itself is systemically racist. Somebody calling that out and keeping it accountable, if they have a good faith basis, I'm all for.”

Bekiempis, for her part, says that for a theory like that to hold sway with jurors, you’d need to have some evidence—“or be a masterful orator.” The whole thing puts her in mind of a case she once reported on.

“I once saw two accused mobsters acquitted in a trial where their lawyers claimed they had been ethnically profiled for being Italian,” she said. “This was a very diverse Manhattan jury. I was shocked but the evidence at trial, while not bearing out this claim necessarily, weighed heavily in the defense's favor. And it didn't hurt that the lawyering was masterful."