Serbia, the largest country of the Western Balkans, faces a historical choice concerning its future political orientation. Although this choice has been on the agenda since the late 1990s, it will remain unresolved for some time to come. The country’s transformation has been moving forward. However, short of integration in western institutions, first of all in the European Union, the process is incomplete and other major players in the international system, first of all Russia but to some extent also China, attempt to influence Belgrade in a direction favorable to their interest. Rational choices in regard to economic integration, trade and investment, and the effects of consolidating democracy should drive Serbia in the direction of the West. However, as demonstrated by some cases, there are factors other than rational choice. Emotional association with Russia, orthodox Christianity, the Russian backing of Serbia in the dispute of the latter with Kosovo, as well as Moscow’s sophisticated influence playing on the West’s step-by-step advancement and hesitation help Russia better establish itself in Serbia. That results in an inconclusive situation that requires attention to avoid the continuation of hesitancy and uncertainty in the long run. China potentially offers an alternative, primarily as a trade partner and investor. However, its interests in Serbia’s future orientation may be different from Moscow’s as its investments may offer higher returns if Belgrade becomes a member of the European Union sooner rather than later.