By Holly Yan, Rebekah Riess, CNN

(CNN) — “This is Sean Combs,” Assistant US Attorney Emily Johnson told jurors in May, during opening statements of the hip-hop mogul’s racketeering and sex-trafficking trial. “To the public, he was Puff Daddy or Diddy, a cultural icon, a businessman, larger than life.

“But there was another side to him. A side that ran a criminal enterprise.”

Jurors disagreed. On Wednesday, 51 days after Johnson promised to make that case, Combs was found not guilty of the most serious charges against him: racketeering conspiracy and sex trafficking by force, fraud or coercion.

How and why did things go sideways for the federal prosecutors from the prestigious Southern District of New York?

Racketeering conspiracy is hard to prove

Racketeering conspiracy – sometimes called a “RICO” charge – doesn’t refer to a specific crime. Rather, it involves people engaging in an illegal scheme. And the charge is difficult to prove.

“When you look at the issue of RICO and racketeering, what you generally look at are mob bosses who have these underbosses who are furthering (a) criminal enterprise,” CNN legal analyst Joey Jackson said.

In Combs’ case, prosecutors claimed he and members of his inner circle had engaged in crimes involving kidnapping, arson, forced labor, bribery and sex trafficking, among others. For a conviction, jurors would have needed to find Combs and at least one other person had agreed to commit at least two relevant acts within a 10-year window.

But jurors never heard any direct testimony from many of the people who prosecutors claimed participated in the enterprise. That’s unusual for a racketeering trial, Jackson said.

Typically, “you have one of those mob bosses or the underbosses come testify saying, ‘He, the one sitting right there, told me to engage in an arson, told me to bribe this one, extort this other person, get money from the other, pass drugs here.’ You didn’t have that, nor did you have other people besides (Combs) sitting at that table,” Jackson said.

Legal experts say the prosecution may have overcharged Combs.

“I think this racketeering charge was an overcharge from the start,” CNN senior legal analyst Elie Honig said.

“If you try to show racketeering as a prosecutor, you have to show that there was an organized criminal enterprise, that there was some structure to this, that there was a criminal operation that was ongoing and that committed multiple crimes. They just did not have that proof,” Honig said.

“Could they prove Sean Combs was a horrible human being, physically abusive, engaged in domestic violence? Yes, yes and yes. But none of those are racketeering.”

The sex trafficking charge didn’t work

The prosecution’s witnesses gave stunning testimony about “Freak Offs” and “hotel nights” – drug-fueled sexual performances they said Combs organized.

Prosecutors charged Combs with two counts of sex trafficking by force, fraud or coercion: one related to his ex-girlfriend Cassie Ventura, and one related to another ex-girlfriend who testified under the pseudonym “Jane.”

Maria Cruz Melendez, who successfully prosecuted singer and music producer R. Kelly for racketeering, wasn’t surprised that Combs was acquitted on the sex trafficking charges.

“At the end of the day, the jury had to be convinced that coercion was happening within the dynamic of that relationship,” Cruz Melendez said.

But the defense argued the women wanted to spend time with Combs because they loved him and their presence at the “Freak Offs” or “hotel nights” was not due to violence and fraud, she said.

In addition, both women had long-term relationships with Combs, which was “unconventional” for sex trafficking cases, Jackson said.

“When you look at sex trafficking, you’re looking at not (a) long-term relationship, generally, of 11 years, as it related to Cassie Ventura, or three years, as it related to Jane,” Jackson said.

Former federal prosecutor Alyse Adamson agreed.

“These were individuals who had been in long-standing relationships with Combs. So there was a thin line between consent and coercion – a thin line that, of course, the defense exploited very effectively” on cross-examination, Adamson said.

Prosecutors ‘got their teeth kicked in’

Even though Combs was convicted on two less serious counts, “the defense won this case,” Honig said.

“The Southern District of New York – the vaunted SDNY, my beloved former office – got their teeth kicked in in this case. There’s no other way to say it,” the former federal prosecutor said. “And the primary thing I attribute that to is they overcharged this case.”

But Julie Grant, a Court TV anchor and former assistant district attorney, said she believes prosecutors made a solid case for the more serious charges – but the jurors didn’t buy it.

“So certainly, with this verdict, we’ve got to respect it, like we do everyone here in America,” Grant said.

CNN’s Karina Tsui contributed to this report.

The-CNN-Wire
™ & © 2025 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.