This article provides a critical analysis of Russia`s political involvements in the Middle East, and examines the successes and failures of Russia`s policies in the region. The article argues that Russia has recently shown, particularly through its Syrian policy, that it is still a diplomatically skilled and politically powerful state in international politics, and that it continues to defined the Middle East along Soviet lines, namely as an area of the world close to Russia’s borders. This has led Russia to develop bilateral relations with the countries in the region, and as such, Moscow feels that it must get involved in the problems of individual states. By the same token, Russia maintains a rivalry with the U.S. in building relations with or conducting interventions in regional countries, indicating a continuum of the traditional strategy. The paper then provides an assessment of Russia`s failures in its bilateral relations with Syria, Palestine, Iraq and Iran respectively. The article concludes that Russia is failing to convince Middle Eastern states to listen to its advice.