Diddy Goes on the Offensive After Conviction—May Sue Cassie to Reclaim $20M Settlement
New York, July 2, 2025 — Just one day after being found not guilty on the most serious charges brought by federal prosecutors, Sean “Diddy” Combs is shifting his legal strategy—from defense to offense.
Though the hip-hop mogul was convicted of two federal prostitution charges, he was acquitted of sex trafficking and RICO charges, and is now awaiting sentencing later this fall. In the meantime, Media Take Out has confirmed that Diddy’s legal team has reached out to President Donald Trump, formally requesting a presidential pardon. According to insiders, Trump remains “receptive” to the request, though no official decision has been made.
But while his criminal attorneys focus on possible clemency, Diddy’s civil legal team is gearing up for battle.
Turning the Legal Tables
Media Take Out has exclusively learned that Diddy has empowered his civil attorneys to aggressively counter-suethe individuals behind a growing stack of lawsuits filed against him over the last year. Many of those suits include highly inflammatory and often unproven allegations, ranging from abuse to assault to financial misconduct. Now that the federal jury rejected the majority of the criminal claims, Diddy and his team believe it’s time to go on the attack.
“He’s done playing defense,” said one person close to Combs. “Now it’s about holding people accountable for what they’ve said and done.”
Targeting Cassie Ventura
And at the top of Diddy’s list? Singer Cassie Ventura, his former longtime partner.
According to a Media Take Out insider, Diddy’s attorneys are exploring legal action to recoup the reported $20 million settlement he paid Cassie in 2023 to resolve her civil claims of abuse and misconduct. The key issue? A non-disclosure agreement (NDA) embedded in the settlement.
Cassie’s testimony during Diddy’s federal trial was delivered under subpoena, which means it’s legally protected and does not violate the NDA. However, Media Take Out has learned that Cassie and her legal team made several public statements to the press—both during and after the trial—that may not be protected under the NDA’s legal carve-outs.
Diddy’s lawyers are reportedly reviewing the language of the NDA line-by-line, looking for any opening that would allow them to argue breach of contract—and possibly demand the return of the multi-million-dollar payout.
“It’s not personal,” the insider said. “It’s business. A deal was made. If that deal was broken, Diddy wants his money back.”
The Bigger Picture
This potential legal action signals a dramatic shift in posture for Combs, who spent much of the past year entangled in a storm of lawsuits and criminal investigations. While the two convictions are still serious—and carry a maximum sentence of 20 years—the not guilty verdicts on the trafficking and RICO charges were seen by many in his camp as a major vindication.
With sentencing months away and a possible Trump pardon on the horizon, Diddy’s team believes now is the time to reclaim control of the narrative—and his fortune.
What’s Next
- Sentencing on the prostitution charges is expected this fall.
- Trump pardon discussions are ongoing and could materialize at any time.
- Diddy’s civil legal team is expected to file motions targeting his accusers in the coming weeks.
- Potential breach of NDA lawsuit against Cassie Ventura is currently under legal review.
Whether Diddy will succeed in reclaiming his settlement money—or silence his critics—remains to be seen. But one thing is clear: he’s not retreating quietly.