In US foreign relations with hostile states, President Obama declared in his inauguration speech this week, "engagement can more durably lift suspicion and fear." With his reelection behind him--in which he garnered more Cuban-American votes in Florida than any Democrat in history--and his legacy in front of him, here are steps the president should take to engage the Castro government and forge a sensible, sane, and productive US policy toward Cuba.
(1) Remove Cuba from the State Department list of nations that support terrorism. Among The Nation’s list  of twenty ways the president should exercise his executive power is this long-overdue action. Cuba’s designation as a supporter of terrorism is an enduring injustice. Yes, Cuba has some criminal fugitives living on the island. But it is hard to accuse Cuba of harboring terrorists while Luis Posada Carriles, a prolific lifelong terrorist, is living freely in Florida. Moreover, Cuba’s current efforts to host and mediate a cease-fire and permanent peace accord between the FARC and the government of Colombia is hard evidence that it is playing a constructive role in seeking to end conflicts that breed terrorism in the region.
(2) While we are on the subject, Obama should order the arrest of Luis Posada Carriles and hold him under the Patriot Act until his extradition to Venezuela, from which he is a fugitive for the terrorist crime of blowing up a civilian airliner in October 1976, can be arranged. When the Bush administration let Posada set up residence in Miami in 2005, Venezuela sent a formal extradition request. If Obama is serious about fighting terrorism, he should finally grant that request.
(3) With Cuba off the terrorism list, Obama should end the economic and commercial sanctions that have accompanied its designation as a terrorist nation. The Department of the Treasury would thus cease to fine international banks for doing business with Cuba, which has undermined Cuba’s slow evolution toward a more capitalist-oriented economic system.
(4) And to support economic changes currently underway in Cuba, Obama should expand the general licensing for travel to Cuba of businessmen, scientists, citizens and others associated with industries like agriculture, travel, construction, oil, automobiles, healthcare and more. While the travel ban itself cannot be lifted without a majority vote in Congress, the president can create categories of general licensing that will allow far more Americans to freely travel to Cuba. Such a decree would instruct the Office of Foreign Assets Control to stop playing the role of travel dictator and simply provide all necessary licenses to travel agencies and educational interest groups involved in promoting travel to Cuba. Now, ironically, Cuban citizens are more free to travel here than US citizens are to travel there, since the Castro government lifted more than fifty years of restrictions on the ability of its citizens to travel freely abroad, earlier this month. If Obama is to be true to his overall commitment to advance civil rights, he can begin with the basic civil right of allowing US citizens to travel freely to Cuba.
(5) The president should also reconfigure the so-called “Cuban Democracy and Contingency Planning Program” mandated by the Helms-Burton Act and run out of USAID, from the failed “regime change” orientation to a set of transparent, non-interventionist “people-to-people” programs. Incoming Secretary of State John Kerry, who knows quite a bit about USAID's misconduct in Cuba from his tenure as Chair of the Senate Foreign Relations Committee, should immediately move to review and revamp the goals and operations of these misguided and counterproductive regime change efforts.
(6) To engage Cuba with normal diplomacy, Obama should order a bilateral dialogue on all areas of mutual interest: environmental cooperation, counternarcotics operations, counterterrorism, medical support for Haiti and more. On the agenda should be the case of contractor Alan Gross, who was sent to Cuba by the USAID Democracy Program on a quasi-covert mission to set up independent satellite network communications systems, and then abandoned to his predictable fate of being caught and tossed in jail. It’s time to let him return home to his family.
(7) Finally, Obama should commute the sentences of the so-called “Cuban Five”: Fernando González, Antonio Guerrero, Gerardo Hernández, Ramón Labañino, and René González (who is now on parole). These intelligence operatives were actually counterterrorism agents focused on anti-Castro exile groups that, frankly, have posed a threat to Cuban citizens and national security interests alike. All of them have served more than twelve years in US prison. They have been punished enough and also deserve to return home to their families.
Go here  for more on how Obama should use his executive power to push a progressive agenda.