Obama's Legacy on Cuba

The media has been abuzz about U.S. policy toward Cuba. Most prominently, the New York Times  has been running editorials, including this one today:

President Obama could help expand the role of Cuba’s small but growing entrepreneurial class by relaxing sanctions through executive authority and working with the growing number of lawmakers who want to expand business with Cuba. The White House could start that process by removing Cuba from the State Department list of countries that sponsor terrorist organizations and making it easier for Americans to provide start up-capital for independent small businesses. Doing that would empower Cuban-Americans to play a more robust role in the island’s economic transformation. More significantly, it would gradually erode the Cuban government’s ability to blame Washington for the shortcomings of an economy that is failing its citizens largely as a result of its own policies.

For the first time, I am actually starting to think this will happen. Cuba has bedeviled presidents for decades, and his legacy can be cutting the Gordian knot with executive action. Here's why he would do that:

1. Executive action is the only way he can relax the embargo because Cuban Americans in Congress won't let anyone touch the Helms-Burton law.

2. He has already set the executive action precedent with immigration, which is rallying people to his side and getting them excited.

3. The Summit of the Americas is coming up in April 2015 and all everyone is talking about is the administration's response to Cuba's presence there. With sweeping executive action, Obama can undercut Raúl Castro's stale talking points about the "bloqueo" and hammer him with a blistering speech about human rights and freedom.

4. Those who will excoriate him for this action already dislike him passionately, so this will not newly alienate very many people.

5. He can use it as leverage to get Alan Gross out of prison. Cuba has historically responded to gestures, and it has been begging for an end to the embargo (even the Castro brothers have benefited so much from it and almost certainly don't really want it to end in their lifetimes).

6. This would give him a real foreign policy legacy, which he will not get from the Middle East.

This last point is important. Obama's foreign policy has been characterized largely by mopping up his  predecessor's ill-advised policies. A major action on Cuba would be the sort of bold policy he could hang his historical hat on.