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Cuba has merited five decades of American punishment because its domestic policies were disobedient to Washington. This article examines whether President Barak Obama will continue to demand that one sovereign state demand submission from another. Assuming his honesty and good intentions, Obama will encounter a problem in the mind-set of the elite Washington policy circle, which has thought little about Cuba. In 1991, most of them rejoiced when Cuba's economy virtually collapsed following the demise of the Soviet Union. But official American attitudes, shaped by Cold War views and the strength of Cuban-American opponents of the Castro government, have not only been passed by, but also have shown to be hollow. Cuba continues to resist and survive—but has been wounded in the process. Looking at the hubris of American policy toward Cuba and the odyssey of post-Cold War Cuban-American relations allows for understanding why President Obama announced at the Trinidad meetings of hemispheric nations in April 2009, the end of one of the United States' most stupid, long-enduring and unfair policies. [ABSTRACT FROM AUTHOR]