Nicolás Maduro, the ousted Venezuelan president who was hauled from his Caracas home by US special forces in January and now sits in a Brooklyn jail facing narcoterrorism and drug trafficking charges, has recruited a lawyer who helped disgraced hip-hop legend Sean "Diddy" Combs (aka P. Diddy) walk free on the most serious counts at trial, in what amounts to one of the more surreal legal team-ups in recent American judicial history.

Court records filed on June 4 cited by Reuters show that Anna Estevao, a partner at New York boutique firm Harris Trzaskoma, has joined the former president's defence. Estevao was part of the legal squad that secured acquittals for the rapper on sex trafficking and racketeering charges that could have put him away for life — a result that drew gasps from courtroom observers and generated weeks of tabloid coverage last year. Combs was ultimately convicted on two lesser prostitution-related counts and is serving a 50-month sentence at a federal facility in New Jersey while he appeals.

Maduro, who has pleaded not guilty, was seized on January 3 in a US military raid on his Caracas residence, a lightning operation his own lawyers have denounced as an "abduction," and whisked to New York, where he has been detained ahead of trial. The move, which essentially ended more than two decades of socialist rule in Venezuela, came after years of US indictments that had long seemed more symbolic than enforceable. Maduro’s former deputy, Delcy Rodriguez, has since taken on the role of acting president with Donald Trump’s blessing, and has been willing to accommodate US demands to open Venezuela's oil and mineral riches to American investors.

Estevao arrives two days after a separate development that already made legal-world eyebrows rise: the announcement that Maduro's Washington-based counsel, Barry Pollack, was himself joining Harris Trzaskoma. Pollack, who had previously been at Harris St Laurent, has signalled that he intends to challenge the legality of his client's capture in court: a constitutional argument that, if successful, could see the charges dismissed on procedural grounds before a jury is ever seated.

Estevao's courtroom record gives prosecutors reason to be watchful. At Combs' trial, she cross-examined Casandra Ventura, the hip-hop impresario's former girlfriend and the prosecution's star witness, who had accused him of coercing her into degrading sexual performances. The attorney presented the jury with emails and text messages from early in the couple's relationship, some of them sexually explicit, in an effort to cast doubt on Ventura's account. The approach contributed to the jury's decision to acquit on the gravest charges.

Whether the same forensic skill at dismantling witness credibility will translate to a narcoterrorism case with geopolitical stakes of an entirely different order remains to be seen. Maduro's next court date is June 30, when his lawyers are expected to appear before a federal judge in Manhattan to outline their pre-trial motions, including any attempt to have the charges thrown out altogether.

The Manhattan US Attorney's office, which has prosecuted both Combs and Maduro, declined to comment. Maduro and his wife, Cilia Flores, have pleaded not guilty to charges including narcoterrorism and cocaine importation. In April, the US Treasury's Office of Foreign Assets Control issued amended licences allowing their defence costs to be covered under restricted conditions. Trial is not expected to begin for at least one to two years.