Gross, who is now 64, was hired by a USAID contractor, Development Alternatives Inc., to deliver satellite Internet equipment to Cuban Jews as part of a program funded as part of the 1996 Helms-Burton Act, which authorized the U.S. government to engage in “democracy building efforts” that would speed the removal of the Castro brothers. How, you ask, could the provision of a modest quantity of satellite Internet equipment to Cuba’s tiny — and notably unpersecuted — Jewish community, a community that already has access to the Internet (I e-mail with its members quite frequently), speed the downfall of Fidel and Raul Castro? If you can figure out the answer to this question, then you could work for the U.S. government. …

And then he was, in essence, abandoned by the government that sent him to Cuba.

His lawyer in Washington, Scott Gilbert, told me last week that, when he described the harebrained mission USAID hired his well-meaning but entirely unprepared client to carry out, government officials reacted with a combination of amusement and horror. “I ask people, ‘If this project came across your desk when you were at USAID, what would you have thought?’ The answer I often get is that they would have thought it was an interoffice practical joke.” He went on, “I’ve been told by former USAID officials that never in the history of that agency have they sent a civilian into an environment like that of Cuba, a country with which we have no diplomatic relations. As I’ve told U.S. government officials, you knew with certainty that he would be arrested. Anyone who has visited Cuba would understand that. What you guessed wrong on was the severity of the penalty.”