By Brett Daniel Shehadey
Special Contributor for In Homeland Security

President Barack Obama, in a somewhat surprising announcement, stated his intentions Wednesday to formalize diplomatic relations between the U.S. and Cuba. He has advocated a long-term policy of engagement with Cuba that would see the opening of an American embassy in Cuba, promoting greater transnational communications, business opportunities and trade.

For some 50 years, Washington has failed to topple the Castro regime through a long-standing policy of isolation, using political and economy sanctions. Many, including the president, have demanded a change in tactics after what they now consider an unsuccessful approach that attempted to punish Cuba for nationalization, political and human rights abuses. The bottom line, they argue, is that it has not worked and it is not likely to work in the future.

Cuba is growing inch by inch in spite of American sanctions. It continues to have ties with some American strategic competitors like China, Russia or even Venezuela. With states ignoring the ban against Cuba and new leader Raul Castro, Cuba is still etching along as a state trapped in amber, viewed to be held back only by the U.S. Many feel that the economic road of normal U.S.-Cuba relations will raise the voices of the people and let them advance as a nation.

President Obama’s announcement came after Havana’s release of American contractor Alan Gross, who was held for what Cuba referred to as suspected espionage and was part of a swap agreement with the U.S. government that traded three incarcerated Cuban intelligence officers held in America.

The president’s decision to move forward with Cuba is mixed within American politics and polarized around two themes: progress and penalty. The reason to formalize relations with Cuba is argued in and of itself both the premise and conclusion. America must move forward with a renewed 21st century approach because no one else will. Cuba will not contact us. The Cuban people deserve better access to American markets and vice versa which will raise their quality of life.

The argument against the president’s engagement with Cuba effort was eloquently stated this afternoon by Senator Marco Rubio (R-Fla.), who correctly noted that the latest act does not demand any apparent political concessions on behalf of Cuba. Havana will not be obligated to politically reform. Nothing but hope and outstretched goodwill presents itself from Washington to Havana. Rubio has called the president’s actions “appeasement,” bowing down to increasing international pressures and a negative image. Rubio also pointed out several instances where the Cuban government has taken advantage of the president’s previous steps, such as easing travel restrictions.

The argument to penalize the Castro regime or to wait for Cuba to internally reform, seemingly has an equal measure of doubt. The conservative ‘hold-the-line’ strategy is also possibly insufficient. It has become more of a matter of pride to deny Cuba normal relations not because of an abusive regime, because it deals with many other even more abusive regimes, but because of Cuba’s long history.

Washington’s many blunders include: the failed Bay of Pigs invasion to liberate the people by removing the regime and freeing the people, exploding cigars to kill Castro and the last 50 years of stagnant neglect and punishment.

For all we know, there has been a secret dialogue between Washington and Havana. We are led to believe that a simple executive decree, an epiphany or outpouring of emotion has taken place in the White House. The politics at play is that the president is looking for a legacy beyond the Affordable Care Act.

The administration has responded to the underlining question of ‘What next for Cuba?’ The remaining question is, ‘Will this new policy work to produce anything resulting in liberal democracy at all?’ Will it free the Cuban population from the tyranny of their government? Will it give them real access to human rights, freedom of speech or the rule of law? A simple bout of diplomacy gaming might answer all of these questions and more if enough relevant factors (including recent and applicable political profiles of Raul and the elite) were inserted into the policy simulation. But has this been done, really?

Whatever Washington decides in the end, it must guarantee that it will continually act in the best interest for the American and Cuban people from now on, regardless of the past. The president has said that this is “fundamentally about freedom and openness.” He has even asked Secretary of State John Kerry to review Cuba’s sponsorship of terrorism.

The administration would be wise to establish a bipartisan review of Cuba in cooperation with the House and determine the best options to move forward, if possible, while formalizing diplomatic relations.

Sharing a piece of one’s political legacy with oppositional political leaders this time may ensure its success.