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"This is Sean Combs," Assistant U.S. 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 proveRacketeering conspiracy – sometimes called a "RICO" charge – is difficult to prove. Racketeering isn't a specific crime; rather, it involves parties engaging in an illegal scheme.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 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 allegedly were part of the enterprise. And 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."Why the sex trafficking charge didn't workThe 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, CNN legal analyst Joey 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.CNN's Rebekah Riess and Karina Tsui contributed to this report.