This study appeals to readers yearning for a comprehensive assessment of the issues that will impact President Barack Obama's stewardship of U.S. foreign policy. This study commences with an examination of Obama's foreign policy evolution-tracing early writings, the critical speeches, interviews, performance during presidential debates and during his "honeymoon." It is at this point the author offers a brief assessment of the strengths and weaknesses of his competence in foreign policy. Thereafter this study explores the opportunities and pitfalls that will govern President Obama's tenure. The opportunities afforded to Obama include but are not limited to the following: his central objective is to transform the American image around the world; why Obama is determined to end the unilateralist impulse and shift US foreign policy to its historic multilateral traditions. Obama is moving swiftly to place his stamp on U.S. policy in Iraq and Afghanistan; the new president is determined to confront Al Qaeda, examines Obama's use of personal diplomacy to engage Iran, Cuba, and Syria; explores the president's objectives to resolve the long-simmering Israeli-Palestinian dispute. Conversely, the study highlights a number of issues that may produce a host of problems for President Obama on the international front. In one scenario Obama's decision to implement a "phased withdrawal" of U.S. forces from Iraq may unleash a new period of violence and undermine the gains made by the armed forces of the United States and Iraq. Second, evidence will be presented to illustrate why the failure to defeat the Taliban in Afghanistan, along with the inability to contain, if not defeat Islamic extremism in Pakistan, may undermine the war on terror and may dramatically impact Obama's opportunity for reelection. Significantly, the study demonstrates why the historic Democratic Dilemma will emerge as a critical variable to exemplify why President Obama's tenure will be replete with problems.