This research paper offers a snapshot of the privatization of the military in Russia, as revealed in the subtext of the conflict in the Donbass region, followed by the Russian intervention in Syria. Although phenomena such as the Wagner Group may appear at first sight to be innovations, the recourse to non-state groups in combat operations is nothing new for Moscow. A distinction should therefore be drawn between the Russian private military companies that are genuinely comparable to the conventional PMCs existing elsewhere in the world and the armed groups operating more along the lines of “war by proxy” instigated by Moscow. This paper also examines the prospects for private military companies in Russia and the consequences of their possible legalization.