Russia’s military involvement in Syria from September 2015 led to the collapse of the rebels opposing the regime and secured the continued rule of Syrian President Bashar al-Assad. In the short term this reinforced Russia’s regional and international standing, and encouraged Moscow’s hopes of economic and political fruits. Yet over time, Moscow saw it was unable to restore security and stability to Syria and advance the country’s reconstruction, and finds itself sinking in the mire of local enmities within Syria, as well as the mire of regional enmities. These entanglements have become a Russian problem, and Moscow finds itself with no readily available solution. In addition, Russia’s hopes of leveraging its Syrian achievements against the United States in order to promote Russian interests elsewhere in the world have been dashed. Consequently, involvement in Syria, which at first looked like a knockout against rivals and enemies, has become a source of strategic discomfort for Russia. Significant resources, time, and effort must clearly precede any enjoyment by Russia of the fruits of military achievements in Syria. In the final account, it is impossible to shake off the impression that the days of world wars, both hot and cold, have long gone, and with them the importance of military strongholds, which, rather, become a source of political, military, and above all economic headaches for those that try stubbornly to cling to what they see as an expression of national strength or a source of economic gains. It is true that Russia is the current winner in the “struggle for Syria,” and there is no doubt that the determination and military force it demonstrated are important for its regional and international status. Nonetheless, it is still hard-pressed to reap the fruits of its victory.