Even before becoming President, then Senator Obama campaigning for his first presidency warned George Bush and Dick Cheney about Iran and that “they must hear loud and clear from the American people and the Congress: You do not have our support, and you do not have our authorization, to launch another war.” Obama reminded the public that the fateful decision to invade Iraq in 2003 had only enhanced Iranian influence. Instead of issuing threats, he argued for direct negotiations and diplomacy with Iran. Following his election as President in 2008, Obama sent letters to Iran’s Supreme Leader Ali Khamenei. In his letters to the Iranian leader, Obama urged strategic engagement with Iran, and called on the Iranian leader to resolve the nuclear dispute. Yet, in 2009 Iran was beset with internal uprisings following disputed presidential elections that kept Ahmadinejad in power for another four years. After the 2009 elections, a major political rift between Khamenei and Ahmadinejad undermined Khamenei’s reputation and influence inside the country. After lending strong support to Ahmadinejad, the latter turned out to be the worst nightmare for Khamenei. By 2013 presidential elections and arrival of Hassan Rouhani, Khamenei had been weakened and was forced to accept the results of 2013 elections that led to the emergence of a moderate “who ran on a reformist platform, promising a solution to Iran’s nuclear negotiations and the Iranian people’s need for relaxing the sanctions.” Obama’s persistence and patience paid off, and now he has a historical chance to make his legacy with Iran.