On February 4, the Cuban government announced it will demand a 20-year prison sentence for U.S. citizen Alan Gross. The 61-year-old Maryland resident was arrested in December 2009 in Havana after visiting Cuba to distribute satellite phones to Jewish and other civil society groups. Although details of his activities remain sketchy, Gross was employed by Development Alternatives, Inc., a U.S. State Department contractor, rendering democracy support work in the field. Gross was helping deliver technologies of freedom that Cuba’s leaders greatly fear.

After over a year in jail, Gross, who is in declining health, is now formally charged with the commission of acts against “the integrity and independence” of Cuba. A Havana show trial will soon follow.

The case is of high importance to the Obama Administration. Assistant Secretary of State for the Western Hemisphere Arturo Valenzuela noted on January 11 that the Obama Administration “made it clear to the Cuban authorities that it’s very difficult to move to greater engagement in the context where they have continued to hold Alan Gross.” Cuban readiness to prosecute and condemn Gross to a slow death in a Havana prison is a heavy blow to the Administration’s soft policy of enhanced engagement.

Over the past two years, the Obama Administration has sought to improve ties with Cuba by using executive authority to lift restrictions on travel and the dispatch of remittances to the island. The last round of liberalization measures were introduced in early January. It has also conducted several rounds of immigration talks with senior Cuban officials.

The underlying assumption of this policy is that greater access to the island by Cuban–Americans, more “people-to-people” exchanges, respectful dialogue on issues of mutual interest, and easier transfers of remittances will build shared confidence and closer ties. Since 2009, the Obama Administration has distanced itself from the tough, pro-democracy stance of the Bush Administration, frequently derided as a strategy of “regime change.” Obama has embraced a strategy aimed at dialogue, tension reductions, and readiness to engineer a “soft landing” as the Castro brothers fade from the political scene and a succession crisis looms on the horizon.

Yet, not unexpectedly, Cuban behavior in the Gross case is consistent with previous responses to U.S. openings. Once more the open hand of the Obama Administration encounters the clenched fist of Cuban tyranny. While less tragic, the Gross case is reminiscent of events such as the cold-blooded murder of four Cuban-Americans belonging to the Brothers to the Rescue in 1996. This brutal act torpedoed a budding effort by the Clinton Administration to improve relations with the Castro regime.

Cuba’s message is clear: At the political core of the regime are its rejection of open dissent, pluralism, and genuine democracy and a reaffirmation of the principles of democratic centralism and political conformity so central to the Marxist–Leninist regime. It is also a reflection of deeply rooted anti-Americanism and “siege-mentality” situated at the core of the regime’s ideology.

In Cuba, where all justice is political, there are still avenues open to Raul Castro. He can magnanimously pardon Gross after a conviction. At the back of Raul’s mind may be further pressure on the U.S. to pardon or release the so-called Cuban Five, who are charged with spying for Cuba in the 1990s. Many in the Obama Administration and Democrats in Congress are hoping the Gross case will be just a speed bump on the way to better relations with the Castros. In the interim, Gross faces a bleak and unjust incarceration.

When the world’s eyes are focused on Egypt and growing demands for real democracy there, Cuba—90 miles from the U.S.—remains a bastion of anti-democracy ruled by the Castro brothers for more than 50 years. Standing up for democracy in Egypt should not be matched by silence on Cuba.