Diddy’s Legal Strategy Praised By OJ Simpson’s Lawyer, Weird Connection To Trials Exposed

Diddy and OJ Simpson

Diddy’s courtroom gamble paid off as O.J. Simpson’s former lawyer Robert Shapiro applauded the defense for securing a rare federal acquittal.

Diddy walked out of a Manhattan courtroom cleared of the most serious federal charges against him after a two-month trial that drew national attention and legal comparisons to one of the most watched cases in American history.

The Hip-Hop mogul was acquitted of sex trafficking and racketeering conspiracy charges on July 2, 2025, in New York’s federal court.

The jury did convict him on two lesser counts of transporting individuals to engage in prostitution. His sentencing is scheduled for October 3.

The defense team’s decision not to have Diddy testify was a calculated move that drew praise from legal heavyweight Robert Shapiro, who famously helped secure OJ Simpson’s 1995 acquittal.

“The defense team did a terrific job on a case the U.S. Attorney overcharged. An acquittal in Federal Court is highly unusual. Congratulations to Mark and Tenny for building an incredible group of talented lawyers,” Shapiro told Fox News.

Diddy’s legal team, led by Teny Geragos and Marc Agnifilo, included a lineup of seasoned attorneys: Brian Steel, Anna Estevao, Jason Driscoll, Xavier R. Donaldson and Alexandra Shapiro.

Harvard Law professor Alan Dershowitz also weighed in on the trial’s outcome, comparing the strategy to Simpson’s defense.

“Ultimately, the smart decision was not putting OJ on the witness stand. The smart decision here was not putting Combs on the witness stand. The difference is we want a complete victory. They got a partial victory, but an almost complete victory, so I commend them for excellent work,” Dershowitz said.

The trial, which began on May 5, centered on whether Diddy operated a criminal enterprise or engaged in consensual adult relationships.

Prosecutors argued the Hip-Hop mogul used his influence to exploit women. The defense countered that the government exaggerated the case and blurred the line between personal behavior and criminal conduct.

The jury sided with the defense on the most serious allegations, delivering a rare federal acquittal that legal experts say is a difficult achievement.

Shapiro’s involvement in the OJ Simpson case remains one of the most scrutinized moments in legal history.

OJ Simpson, a former NFL star, was acquitted of double murder in 1995 after a trial that captivated the nation. Shapiro helped assemble the “Dream Team” that included Johnnie Cochran and F. Lee Bailey.

Ironically, Diddy’s sentencing hearing is set for October 3, 2025, the same day O.J. Simpson was acquitted.