Cuban President Fidel Castro (L) and his brother Raul, chat on December 23, 2003 in Havana, during a meeting of the Cuban Parliament. Raul Castro succeeded his brother Fidel Castro as the president of Cuba on February 24, 2008, in a historic power shift expected to keep Havana firmly on its communist path, officials said.

The conviction and sentencing of American contractor Alan Gross surely leaves a bitter taste in the mouth of the Obama Administration days before it embarks on a Latin American trip. Opting to “play it careful and safe” and “hope the Cuban dictatorship does the right thing” did not spare the Maryland man from receiving a 15-year prison sentence.

Gross, 61, was detained by Cuban officials in December 2009 for delivering communications equipment to a small Cuban Jewish community. He was part of a USAID fund to expand communication access on the island. Former State Department spokesperson P. J. Crowley defended the program and Gross, saying he is a “dedicated international development worker” who visited Cuba to donate satellite equipment to “help the Cuban people connect with the rest of the world.”

The Castro regime points to the incident as evidence of a U.S. conspiracy to undermine the regime. Last week, a Cuban TV special aired a report on what it calls cyber war launched by USAID and other U.S. agencies. Events in the Middle East and the current economic crisis have exacerbated Cuban officials’ paranoia.

While enemies of Cuban democracy promotion want to blame the Bush Administration for Gross’s arrest and conviction (just as the Kennedy Administration blamed the Bay of Pigs fiasco on President Eisenhower), the detention of Gross occurred after the Obama Administration had been in office more than 10 months.

“With Mr. Gross’ sentencing, the Castro regime has effectively demonstrated the hopeless and dangerous naïveté of this Administration’s policy toward the regime,” commented Senator Marco Rubio (R–FL).

Representative David Rivera (R–FL) complained to Secretary of State Hillary Clinton on Tuesday that there was no planned U.S. response to the conviction of Gross. The Obama Administration has embarked on a policy of enhanced engagement with the Cuban people, loosening restrictions on travel and the flow of remittances to the island. This attempt to improve the U.S.–Cuban bilateral relationship have done little, if anything, to persuade the Castro regime to loosen its chokehold on the freedoms of the Cuban people.

We must increase pressure on the regime until the basic rights, freedoms, and dignities of the Cuban people are respected,” urges Representative Ileana Ros-Lehtinen (R–FL), chairwoman of the House Foreign Affairs Committee.

It is widely predicted that Raul Castro will release Gross by executive order on humanitarian grounds. Many liberals on the Hill are hoping that will be the case so as not to endanger closer ties.

Failure by President Obama to raise the case of Cuba and its fundamental repression of individual liberty while in Latin America will only demonstrate a lack of resolve when it comes to the future of democracy so near to home.