Federal prosecutors have portrayed wealthy Mexican businessman José Susumo Azano Matsura as a supervillain who was always one step ahead of the law. For two decades, prosecutors said, federal agents investigated Azano for drug trafficking, money laundering, extortion and tax fraud to no avail before he was popped last year on charges he illegally donated to San Diego politicians.

But the relationship between Azano and the U.S. government is more complicated than the Justice Department has let on.

In early 2012, the State Department vetted Azano and signed off on his participation in a deal to sell U.S.-made electronic surveillance equipment to Mexico, according to a redacted copy of a State Department export license obtained by Voice of San Diego.

That means, experts said, that the State Department didn’t believe Azano’s involvement in a deal to sell military-grade surveillance technology was a security risk even though the transaction occurred while Azano was facing federal scrutiny for serious offenses.

“If the U.S. government was investigating him for another crime, it does seem unusual that they would issue a license,” said Colby Goodman, who studies U.S. foreign security issues for the nonprofit Center for International Policy’s Security Assistance Monitor.

Azano’s license from the State Department raises a troubling question: Why did the U.S. government allow someone it believed might be involved in drug smuggling and other major crimes to sell sensitive American surveillance technology abroad?

State Department officials and federal prosecutors declined to comment. Azano attorney Knut Johnson, who provided the license to VOSD, said the State Department’s approval shows that his client is hardly the criminal mastermind prosecutors have made him out to be.

“Mr. Azano has maintained good relations with agencies in the United States, Mexico and elsewhere related to his business, and his good relations with those agencies has been a hallmark of his business,” Johnson said.

Johnson said Azano has received at least two other State Department licenses to export similar U.S. surveillance technology to Mexico.

Azano’s a big player in electronic surveillance equipment across the world, particularly in his home country. He served as the middleman in a series of deals starting in 2011 to sell hundreds of millions of dollars in advanced, Israeli-made spy gear to the Mexican defense department. The State Department export license is the first documented proof that Azano also has dealt in American-made technology.

Johnson said he redacted information from the license for security reasons so it’s unclear exactly what the equipment was and who in Mexico was going to use it. But key information is disclosed in the document.

Azano was working with TCI International, a Bay Area company that specializes in monitoring radio and electronic spectrums. The company has publicized the sale of its equipment to the governments of Botswana, Mozambique, Qatar, Thailand and other countries, though not the deal with Azano. A company official declined to comment on the transaction.

By law, the State Department must approve the export of any sensitive military technology abroad. Agency officials review all parties in the deal before signing off. On the license, Azano’s company, Security Tracking Devices, is listed as the “foreign consignee” – the middleman between TCI International and the agency buying the equipment in Mexico.

“The State Department is pretty thorough,” Goodman said. “They want to know everybody involved in the deal.”

While the actual technology exported to Mexico has been redacted, the license lists the equipment involved as electronic surveillance designed for intelligence purposes. Technology classified this way is primarily for military or defense uses, said Robert Morgus, who researches surveillance exports with the nonpartisan think tank New America.

“This is akin to arms trading,” Morgus said.

Azano’s export license isn’t the only evidence that his relationship with U.S. authorities wasn’t entirely adversarial. When federal investigators began pressuring him, Azano solicited the help of an FBI agent with whom he had met previously.

Starting in 2011, Department of Homeland Security, Immigration and Customs Enforcement and Border Patrol agents began extended searches with police dogs and X-rays of Azano, his family, his employees and his private jet when Azano traveled in and out of the country, according to a complaint Azano later filed with DHS and the FBI and obtained by VOSD. Agents also pressured Azano’s employees for evidence against him by alleging that he was a drug trafficker, the complaint said.

A DHS agent, the complaint said, told one of his pilots, Ramon Castillo Manriquez, that Azano was listed in the department’s computer system as an illegal arms dealer.

Castillo confirmed the account in an interview. He said the harassment from DHS agents was persistent.

“I have never seen the man do anything wrong,” Castillo said of Azano. “Obviously, they were trying to get something on him.”

Azano believed the increased attention he faced was spurred by his dispute with San Diego-based Sempra Energy over a land deal in Mexico.

In September 2012, Azano’s private security guard Ernesto Encinas and another Azano associate met with an FBI agent named Allan Vitkosky to lodge their own accusations about Sempra’s activities in Mexico, said Johnson, Azano’s lawyer. They also wanted to express concern about how federal investigators were treating Azano, Johnson said.

“They believed that Sempra played a role in these harassing searches done by DHS and others,” Johnson said.

Johnson didn’t know how the meeting with Vitkosky was set up, but said that Azano knew the FBI agent because he met with him on an unrelated matter a year earlier.

Vitkosky later told Encinas that the FBI wasn’t going to pursue Sempra, Johnson said. (An FBI spokesman wouldn’t confirm or deny the meetings with Vitkosky.)

Azano was charged in February 2014 with making more than a half-million dollars in illegal campaign contributions to San Diego politicians from late 2011 through 2012. He’s pleaded not guilty. Encinas, his former security guard, has pleaded guilty to related charges in the case.