Federal authorities wrangled a guilty plea Wednesday from a Brazilian man who ran one of the Western Hemisphere’s more flagrant alien smuggling operations, sneaking dozens of illegal immigrants from terrorism-connected countries into the U.S. from 2014 to 2016.

Sharafat Ali Khan specialized in smuggling illegal immigrants from Afghanistan, Pakistan and Bangladesh over to the West, where they would be staged in Brazil before being sent north to try to penetrate the U.S.

One of the men Khan helped smuggle into the country was an Afghan who authorities said was involved in a plot to conduct an attack in the U.S. or Canada and had family ties to members of the Taliban.

Khan appeared in federal court in Washington on Wednesday and agreed to plead guilty to a smuggling conspiracy charge. He will be sentenced this summer and could get up to 46 months in prison, though a lower sentence is likely.

Khan also agreed to accept deportation after he serves his time — though not before making a plea to stay in the U.S.

“I want to stay here. I am a poor person. I would like to stay here if possible. I would like to apply for asylum,” he said, speaking through a translator.

“That’s not part of the agreement,” U.S. District Judge Reggie B. Walton replied, saying Khan had signed paperwork promising to assist in his own deportation once his sentence is completed.

“You’re agreeing to go back to your country,” Judge Walton told him.

“Yes, sir,” Khan said.

The case is part of a stepped-up effort by U.S. Immigration and Customs Enforcement to shut down some of the smuggling rings that shepherd tens of thousands of people up through Latin America and to the doorstep of the U.S.

But the Khan network stood out because it focused on linking would-be migrants in the Middle East with smugglers in the Western Hemisphere, giving potential terrorists a path into the U.S.

The Washington Times first reported on the smuggling network last year but was asked by law enforcement officials to withhold Khan’s name to preserve the investigation. The Times is still not publishing the names of Khan’s clients or his associates in the smuggling operation.

American officials sniffed out the network by interrogating migrants nabbed at the U.S. border and considered the breakup of Khan’s operation an early success.

But the cases also identified worrying problems.

When Border Patrol agents nabbed the Afghan man with terrorist ties and ran his name through the Terrorist Screening Database, he didn’t show up as a danger. But documents reviewed by The Times said he was listed in the FBI’s Terrorist Identities Datamart Environment database as having suspect relations.

Networks capable of smuggling potential terrorists have long been a concern, but the Obama administration tamped down those worries by arguing that the southwestern border wasn’t a likely route for operatives.

However, evidence to the contrary has mounted over the past couple of years, including a smuggling ring that sneaked four Turkish men with ties to a U.S.-designated terrorist group into the U.S. in 2014. They paid $8,000 apiece to be smuggled from Istanbul through Paris to Mexico City, where they were stashed in safe houses before being smuggled to the border.

Rep. Duncan Hunter, a California Republican who learned about the Khan network last year and began prodding the Homeland Security Department for information, said it showed the southwest border was able to be penetrated by people from countries the U.S. fears spawn terrorism.

Agents obtained an arrest warrant against Khan on June 3, after Brazilian authorities executed a search warrant on him to help the U.S. case. Khan, a citizen of Pakistan, was living as a legal immigrant in Brazil.

The Brazilian Embassy didn’t respond to a request for comment about its role in the case.

Khan charged up to $15,000 to smuggle someone into the U.S.

He would get migrants from Pakistan to Dubai and then to Brazil, where they would stage their journey north. They would travel through Peru, Ecuador, Colombia, Panama, Costa Rica, Nicaragua, El Salvador, Guatemala and Mexico before being reaching the U.S. border. The journey could take up to nine months and involved trekking for days through jungles in Colombia and Panama, on foot, with little water.

The U.S. was able to track the route some of them took from Brazil northward because local immigration authorities often encountered them along the way.

Like other networks, Khan relied on local smugglers to recruit clients in his target countries and ship them to Brazil. He then used other smugglers in the Americas to get the clients from Brazil to the U.S. and stashed them in safe houses along the way.

Khan, with the alias “Dr. Nakib,” used the WhatsApp smartphone application to keep in contact with his customers while they were en route. But he told them to delete the conversations when they were caught at the U.S.-Mexico border.

In some of the cases, Khan counted on lax U.S. enforcement to ensure his clients could gain a foothold. He instructed them to show up at a port of entry and turn themselves over to border agents to make claims of asylum.

Other clients would be smuggled across the border but nabbed by Border Patrol agents. They also would claim asylum.

Federal authorities said they have determined that Khan smuggled at least 80 people from May 2014 to June 2016.

At rates ranging from $3,000 to $15,000 per person, that would mean he collected $240,000 to $1.2 million over that 26-month period.

It’s unclear what happened to the money he made. Justice Department attorneys said he had funds stashed in foreign bank accounts, though they didn’t disclose the amount and said the money is probably beyond the reach of U.S. forfeiture laws.

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