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Diddy's Courtroom Pit Bull Now Fighting For Maduro In Manhattan

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Published on June 04, 2026
Diddy's Courtroom Pit Bull Now Fighting For Maduro In ManhattanSource: Wikipedia/Kremlin.ru, CC BY 4.0, via Wikimedia Commons

Anna Estevao, the Manhattan trial lawyer who grilled Cassie Ventura in Sean “Diddy” Combs’s federal case, is now suiting up for a very different client: Nicolás Maduro. The ousted Venezuelan leader is battling U.S. charges in New York, and Estevao has joined his growing defense team as it gears up for what legal observers expect to be a complex and closely watched trial.

According to Business Insider, Estevao, a partner at the Manhattan boutique Harris Trzaskoma LLP, signed on to work on Maduro’s defense this week. The firm also recently brought in veteran trial lawyers Barry Pollack and Susan Hoffinger, a move it touted in a press release carried by Business Wire as a way to expand its firepower in high-stakes criminal and civil cases.

Maduro is facing a superseding indictment from the Justice Department that lays out allegations of narco-terrorism, cocaine-importation and weapons offenses against him and several others. The 25-page charging document is posted by the Department of Justice. The case is being fought in Manhattan federal court, where prosecutors and defense lawyers have already started trading jabs over pretrial procedures and evidence.

Trial Experience And Strategy

Estevao became a national name during her stint on Sean “Diddy” Combs’s defense team, where she handled the cross-examination of the government’s star witness in coverage of the Manhattan trial. Combs was acquitted of racketeering and sex-trafficking charges but convicted on two prostitution-related counts and is appealing a roughly four-year sentence, according to reporting by The Washington Post.

Maduro’s lead lawyer Barry Pollack, who joined Harris Trzaskoma earlier this week, has made it clear he sees the bolstered roster as key to mounting a muscular defense. He told Business Insider that the expanded team will give the defense the resources to mount an “unprecedented” response. Business Insider also noted that Combs and Maduro have both done time in the same federal jail in Brooklyn at different points in their cases, a reminder that a lot of the drama in this story is playing out inside New York’s courthouse and detention system.

The legal talent surge comes as a separate fight over how to pay for Maduro’s defense unfolds in public view. A judge pressed the administration in March about a Treasury rule that blocks Venezuelan government funds from covering Maduro’s legal fees, reporting by the Associated Press shows. A Manhattan judge later set a June return date for more proceedings, according to Law360. Those early battles over funding, access to evidence and potential jurisdictional challenges are likely to shape how, and when, the case finally lands in front of a jury.