This study seeks to analyze Russia's security situation, its relationship with NATO and if NATO can solve, or help solve Russia's security problems. The Cold War set the stage for NATO - USSR/ Russian relationship and this long common history has colored the parties' perceptions and affected their decisions. In the years after 1991 and the USSR collapse, Russia emerged as the leader of the former USSR republics, while it tried to maintain its status and power. NATO continued to function and started an enlargement process creeping closer and closer to Russian borders, infringing on what Russia perceived as its sphere of interests. The tension between the adversaries from the Cold War continued into the twenty-first century. Russia has three significant challenges they need to find solutions to or to mitigate potentially negative outcomes. These challenges include; their overreliance on a raw material based ecomy, a grim demographical trend, and problems associated with the 'near-abroad' nations. Put together these challenges force Russia to reevaluate their security environment. This study concludes that Russia has more significant problems than NATO and that it would be beneficial for Russia to seek a closer relationship with the Alliance. Russia should view NATO as a friend rather than its biggest threat. NATO is the only organization that has the credibility and capability to provide Russia with increased stability and security.