Barack Obama’s final year in office is one with the world in upheaval. It is also the year that will shape the security strategy for the next U.S. president. This commentary paper examines Obama’s security strategy, consisting of a Doctrine of “Strategic Patience” and realistic pragmatism. The core element is in its reliance on diplomatic partnerships or “Partners in Leadership”. The Obama strategy is defined by his management of the Ukraine crisis, the Syrian Civil War as well as in fighting terrorism of the Islamic State in Syria and Iraq. Finally, the paper gives a first look at the legacy of Obama’s security strategy and addresses its implications for Europe and Germany.