The case against ousted Venezuelan leader Nicolás Maduro hasn’t been able to move forward in the past six years.

Now with his capture and first appearance in Manhattan federal court behind him, getting to trial could take even more years, with rings of unusual political and legal battles to come.

The criminal case against Maduro is so legally complex — with his past leadership of Venezuela, the dramatic nature of proving an international narco-terrorism conspiracy and the larger national security and foreign policy implications — that his defense could attempt several different ways of derailing the case before a trial.

Maduro pleaded not guilty Monday to charges of narco-terrorism conspiracy, cocaine importation conspiracy, possession of machine guns and destructive devices and conspiracy to possess machine guns and destructive devices.

“Not that he won’t negotiate, but he will push some of the buttons first,” Dick Gregorie, a longtime Miami-based federal prosecutor, said on Monday after following news coverage of Maduro’s arraignment.

Gregorie had worked on the indictment and trial of Panama’s Manuel Noriega almost 40 years ago, becoming one of the few prosecutors who has successfully tried a foreign fugitive who claimed he was a head of state.

The Noriega case has some parallels to Maduro’s — especially in how rare it is for the US to strike a foreign country and abduct a political leader by force.

It appears likely that the lawyers representing Maduro and his wife Cilia Flores, who also pleaded not guilty Monday to drug and weapons charges, will argue they were captured unlawfully. On Monday in court, the deposed Venezuelan leader said he was “kidnapped” by the US military.

His lawyers will also likely battle with the Justice Department over the evidence in the case, what they can access that may help them, and over the protected national security information that may be able to be used in a trial.

The classified information-handling process overseen by the court can add months to even a straightforward case, and defendants sometimes try to push for the exposure of sensitive information so that the federal government becomes unwilling to try the case, a tactic called “graymailing.”

The evidence collected so far and plans for moving the case toward trial are likely to be discussed at Maduro’s next court appearance in Manhattan, set for March.

An Immunity argument

Maduro is likely to attempt to use his position in Venezuela’s government to argue he has immunity as a foreign leader.

In court, Maduro told the judge he was “still president” of Venezuela. His wife similarly called herself “the First Lady of Venezuela” in her court appearance Monday.

Gregorie recalled how significant a fight the head-of-state immunity claims were with Noriega. They also arose before the bribery trial of a political leader who claimed he was head of state of Turks and Caicos, which Gregorie also prosecuted in Miami some 40 years ago.

“It’s quite clear, in order to get head-of-state immunity, you have to be the diplomatically recognized head of state,” Gregorie said. Other legal scholars have taken the same position, that the US State Department’s diplomatic recognitions are essentially the final word.

The US has maintained since 2024 that Maduro was an illegitimate leader of Venezuela, and instead recognized Maduro’s opposition as president-elect. Still, the answer of who led the country would have to be interpreted by the US court system, potentially up to the Supreme Court.

Noriega lost his head-of-state and diplomatic immunity claims in 1990. He was convicted in 1991 for importing cocaine and given a 40-year sentence.

And Norman Saunders, the chief minister of the Turks and Caicos island nation in the 1980s, wasn’t deemed to be the country’s head of state either, Gregorie recalled. The head of state in Turks and Caicos, a British territory, at the time of Saunders’ case was the Queen.

Will there be cooperating witnesses?

One question that will linger is how intent the Justice Department is to take Maduro to trial.

Removing him from his country makes that easier in one core way: It can shake out new witnesses.

Gina Parlovecchio, a white-collar partner at the large law firm Mayer Brown and former lead prosecutor of the trial against Mexican kingpin Joaquín “El Chapo” Guzmán, said there are likely several cooperators who’ve helped the US Attorney’s Office in the Southern District of New York build the Maduro case.

The office previously prosecuted others with ties to Maduro, including his wife Cilia Flores’ nephews. The federal government also closely tracks the five designated foreign terrorist organizations that are mentioned in the Maduro indictment as taking part in the scheme to move drugs from Venezuela to the US.

Still, having cooperating witnesses appear at a trial can be a challenge.

Gregorie described how one witness died in a suspicious car crash days before he was set to testify against a Noriega co-defendant. Gregorie also noted the killing of DEA informant Barry Seal, by the hired gun of a drug cartel in Louisiana in the 1980s.

“He was murdered before the trial started. There were incidents like that that made you worried,” Gregorie said. “A witness who had documents I was looking for, and those documents disappeared.”

Others in Noriega’s case entered witness protection, giving up their identities for new identities, in towns decided by the federal government, Gregorie said.

“Certainly this business is a violent business,” the retired Miami prosecutor added.

Michael Nadler, another former federal prosecutor on a case against high-ranking Venezuelans, said that drug trafficking conspiracy cases can be more difficult to prove, because of the reliance on witnesses within the drug trade, rather than following the money in foreign bribery cases.

Nadler worked on the Miami money laundering indictment of another top Venezuelan official, Alex Saab, who was released from US custody in a 2023 prisoner swap and returned to Venezuela to work in Maduro’s government.

“You’re going to have to get somebody in the room with him who says he knew about it, he allowed it to happen, or that he did something more,” Nadler said about proving a drug trafficking case.

The indictment against Maduro, however, isn’t as specific on transactions as some drug trafficking and money laundering indictments have been. Yet prosecutors included several episodes, or vignettes, in the now-public allegations against Maduro that appear to suggest they have information from witnesses who had close access to him.

In one vignette, for instance, prosecutors say Maduro told other alleged traffickers they shouldn’t have sent more than a ton of cocaine on a 2013 commercial flight that landed in Paris, and which French law enforcement seized.

The specific moments prosecutors describe in the Maduro indictment link to each of the five narco-terrorist organizations: the FARC and ELN, which produce cocaine in Colombia; the Sinaloa Cartel and the Zetas, which traffic cocaine from central American through Mexico to the US; and Tren de Aragua, which helps to transport cocaine out of Venezuela.

“I almost read it like a greatest hits,” Parlovecchio said.

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Several former prosecutors say the Justice Department would only be willing to indict and capture Maduro if it believed the case was robust enough.

Some prosecutors also believe the ousted leader may want to face a jury.

“I think that they are likely anticipating a trial,” Parlovecchio said, citing how Flores’ two nephews, called the Narcosobrinos, were convicted by a jury of cocaine trafficking in 2016. “These high-level drug trafficking cases do tend to go to trial …. When you have this type of a case, with a defendant who has nothing to lose.”

Maduro’s charges are serious, potentially carrying with them a life sentence for conspiracy plus decades in prison for weapons violations, Parlovecchio said.

She pointed to her case for the Eastern District of New York US Attorney’s Office years ago, where El Chapo also went to trial and was convicted. He is now in the Bureau of Prison’s only Supermax facility, in Colorado, serving a life sentence for the drug trafficking criminal enterprise conviction, plus 30 years for possessing a machine gun.

Making a deal

Yet would the US government be open to some sort of negotiation or deal with the captured ruler?

The vast majority of federal criminal cases end in defendants pleading guilty, either as part of a deal or to avoid a trial, according to federal court data.

A legal and geopolitical deal could arise at any time involving Venezuela — especially if the foreign policy situation changes or the case still lingers after the Trump presidency ends.

However, Gregorie, who tried the Noriega case, said that a drug trafficking prosecution of a foreign leader was always likely to be on the trial track, partly because of the effort it took to charge the case and apprehend them.

“We were constantly pushing to get the case to trial, and if I indicted him, I intended to try him,” Gregorie said on Tuesday about the Noriega case.

Maduro’s defense attorney Barry Pollack, a national security and white-collar defense specialist out of Washington, DC, declined to comment for this story.

Pollack is well-versed in high-profile defendants with a political angle to their cases, having previously resolved the criminal case against Julian Assange. (CNN)

•Venezuelan President Nicolas Maduro, and his wife, Cilia Flores appear in Manhattan federal court with their defense attorneys on Monday, January 5.

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