Is there a reason why U.S. policies worked with Cuba and Iran, but didn't in Iraq or with Russia? Yes. And, as it turns out, it's not that complicated.
If you have been watching hopes for a benevolent "new world order" crash and burn over the past two decades, you might have concluded that the United States isn't very good at foreign policy.
Just consider where the United States was when the Cold War ended, and consider where it is today. In 1993, the Soviet Union was gone, and the United States faced no serious geopolitical rivals. (Can you say "unipolar moment"?) Saddam Hussein still ruled Iraq, but his military power was in tatters and his programs for weapons of mass destruction (WMD) were being dismantled. The Oslo Accords made Middle East peace seem tantalizingly close; al Qaeda was not yet a major force; and Iran possessed exactly zero nuclear centrifuges. A "third wave" of democratic expansion was underway, and sophisticated observers from Thomas Friedman to Francis Fukuyama thought humankind had no choice but to embrace market-based democracy, individual freedom, the rule of law, and other familiar liberal values....
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Walt, Stephen. “The Secret to America's Foreign-Policy Success (and Failure).” Foreign Policy, July 27, 2015