This paper answers the research question: How can game theory be used to understand the interplay between Russia and the West in the time period between 1999 and 2022? by providing an examination and analysis of conflicts including the second Chechen war of 1999, the 2008 war in Georgia and the acknowledgment of the breakaway regions of South Ossetia and Abkhazia as independent states, the 2014 invasion and annexation of Crimea, the support of pro-Russian separatists in Donbas, and the ongoing war in Ukraine. This is done through the lens of game theory, that with help of quantitative-empirical data collection and the use of the epistemological school of thought of positivism, provides an overview of the cause-and-effect relationship between the Russian Federation and the West i.e., the European Union, and the North Atlantic Treaty Organization member states and its allies. The findings of this paper clearly demonstrate a pattern of behavior of the West, that for decades relied on the politics of appeasement, leading to the repeated aggressive behavior of the Russian armed forces under the Russian President Vladimir Putin. As this paper uncovers, these reoccurring aggressions fit within four key strategies that put pressure on the West to achieve what Russia desired. A key part of the empirical data includes major Putin's speeches dating from 2005 to 2022, which help to understand the reasoning and justifications behind his actions. While this paper does not provide a solution to the ongoing war in Ukraine, it offers a theoretical understanding from a game theory perspective of choices that can deter their future reoccurrence.