The Road to Havana

How the U.S. can win over Cuba

By Peter Bjel

With less than two years left in office, U.S. President Barack Obama is intent on leaving an indelible legacy with his presidency. With the possible exception of reaching a nuclear deal with Iran—which remains fraught with uncertainty—nowhere else has this been more apparent than in Washington’s new approach to Cuba, the island nation whose regime has outlasted ten presidencies and defied predictions that it would not survive the end of the Cold War.

With diplomatic relations severed since 1961 and the U.S.’s crippling, still-standing economic embargo against the island, the association looked to be indefinitely irreconcilable. When President Obama and his Cuban counterpart, Raúl Castro, awkwardly shook hands during the funeral of Nelson Mandela in South Africa in December 2013, many responded with disbelief and cautious optimism. This gesture may mark the official beginning of rapprochement between both states.

Nonetheless, serious and trenchant fault lines remain. Conciliatory gestures and statements have been the easy part. Since 1959, Cuba’s geopolitical trajectory has ingrained and cemented its separateness from Washington’s orbit. The real work of settling more than a century of hostilities and resentment that still pervade Washington-Havana relations will be far more difficult. Successful reconciliation of this legacy will determine whether a political and historical breakthrough will …

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