The continued detention of Alan Gross doesn't seem to make sense, but actually, it does if considered in the context of Cuba's proposed economic reforms.
Gross was detained in Havana in December 2009 while working as a subcontractor for Development Alternatives Inc., funded by the United States Agency of International Development. Just three months before his detention, a senior US official, Bisa Williams, traveled to Havana in September 2009 for discussions about direct mail service with Cuban counterparts.
Following Williams' trip, a number of key US officials and Congressional offices talked on and off the record about real openings in US-Cuba relations. Legislation for possible travel to and trade with Cuba was slowly but steadily moving through Congressional requirements with increasing numbers of supporters. There were discussions about "people to people" exchanges for artists and academics, such as the Juanes concert that Williams attended in Havana. In fact, some officials were quietly entertaining the possibility of full negotiations and rapprochement with Cuba in the fall of 2009.
The sentiment was apparently similar on the Cuban side as The Miami Herald reported on December 17, 2010. Wikileaks released a cable about a meeting between top Spanish and US officials in Havana on December 2, 2009 in which Spain's ambassador conveyed Cuba's interest in a "secret channel" to the White House. The top US diplomat in Havana, Jonathan Farrar, sent a cable on December 5 that mentions the interest, but Gross was detained the same day before the US could respond to Cuba's apparent interest in a backdoor channel.
The US response to Gross' detention was uniform and consistent. The Obama administration has said publicly and privately that Gross' imprisonment limits negotiations with Cuban counterparts on even minor issues. Democrats and Republicans in the House and Senate have also called for Gross' release, and legislation to loosen or remove restrictions regarding travel and trade, which was gaining momentum in fall 2009, is now dead.
While there could have been many reasons for originally detaining Gross, the Cuban leadership eventually understood that Gross was preventing advances in US-Cuban relations. A calculation would have been made about the advantages and disadvantages of keeping a US citizen in jail without charging him, so the question must be asked: Does the Cuban government want rapprochement with the US at this point?
Raul has been slowly implementing economic reforms that point towards a centrally planned economy dominated by large state firms but with limited social and political freedom. He has started to address a variety of issues including, land leases, agricultural equipment, ration cards, free soap, subsidized lunches for government employees, bloated government payrolls, as well as limited areas of self-employment.
As part of the reforms, the Cuban government has started laying off approximately 500,000 Cubans which will be followed by an additional 300,000-500,000 in the next year or two. When finished, the government will have laid off almost 10% of Cuba's population and an even greater percentage of the workforce. These individuals represent potential political opposition if even a portion of them take to the streets, so the government will want to take measures to control the unemployed masses. Check YouTube for videos of Raul celebrating Hanukah with Cuba's Jewish community, a creative but clear show of authority aimed at even a small number of individuals that had once accepted Gross.
At the same time, it would seem the Cuban economy would benefit from increased trade with the US and an influx of US tourist dollars, because the Cuban government is basically broke and desperately needs resources. But the Cuban government wants to maintain a tight political hierarchy and control as it reforms the economy, so it needs time to gradually reduce government expenses, unite its two currencies, address high unemployment, create domestic economic sectors and even create a tax base.
Gross' detention, therefore, could be a form of economic and political protectionism for the Cuban government. It allows the Cuban government to focus on domestic issues without intrusions from the north -corporations and investors, the Cuban exile community or even US-funded civil society organizations, such as where Alan Gross was working.
In this scenario, there is little the US Government can do for Gross until Raul is willing to deal, but the US can better understand Cuba's logic for holding Gross. The US should continue to press for his release, as well as support members of Cuban society who lack basic human rights, because reducing or discontinuing the work that Gross was doing would be a disservice to him and Cubans who want the type of assistance he was offering.