The FBI is also continuing to investigate Nader, 60, for contact with another underage boy in 2009, according to the court filing. Nader’s attorneys declined to comment on the filing.

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Nader, an adviser to the United Arab Emirates, acted as an intermediary for members of Donald Trump’s 2016 presidential campaign looking to make connections in the Middle East. He became a key witness in special counsel Robert S. Mueller III’s special counsel investigation of Russian interference in that race after helping to arrange a meeting in the Seychelles between a Trump ally and a top Russian official.

Judge Leonie M. Brinkema on Tuesday again declined to release Nader, given the new information.

“Underlying these three charges is a sordid 30-to-40-year period during which defendant abused his power and wealth to obtain boys for sex and had repeated run-ins with the law both within and outside the United States in connection with his sexual interest in children,” assistant U.S. attorneys Jay Prabhu and Laura Fong wrote. “He used his influence and wealth to purchase introductions to vulnerable boys through intermediaries. Then, over time, he groomed and paid these boys for sex.”

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According to the filing, the youth Nader is accused of assaulting was brought to him by a pimp in Europe. Nader then brought the boy to his home in Washington, where he “sexually exploited him night after night,” according to prosecutors. They allege he took the boy’s passport and threatened to have his mother put in jail if he told anyone what had happened.

Nader’s attorneys have argued that the charge involving the 14-year-old is untrue and too old to be prosecuted. The Justice Department disagrees, saying the statute of limitations was extended in a way that includes this conduct.

The defense attorneys contend most of the evidence against Nader is thin, and they have questioned whether all of the videos of children found on his phone qualify as child pornography and whether he wanted to receive them.

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“None of the messages reviewed to date reflect an interest in, solicitation of, or knowledge regarding child pornography. For example, most of the surrounding text messages are emojis, benign adages and aphorisms, news articles, or irrelevant content and banter,” they wrote in court papers.

Nader’s attorneys argued that his role in Mueller’s probe indicates he could be trusted outside jail, and that he needs to be released for heart treatment. Nader came and went from the country repeatedly while speaking to Mueller’s team last year. But prosecutors noted that he was not charged under seal until April 2018, and did not return to the country until this June.