At first glance, the Chechens and Volga Tatars share several similarities. Both ethnic groups have religious traditions rooted in a regionally particular form of Islam. This is the Khanafi school of Sunni Islam, which combines traditional, Muslim law (Shariah) with local customs influenced by Sufi brotherhoods. In addition, both Chechens and Volga Tatars were incorporated into the Russian Tsarist Empire against their will as a result of military conquest. Moreover, both peoples suffered mightily during the repressive Stalinist period, but also experienced certain degrees of modernization, urbanization and industrialization. Lastly, both peoples occupied similar rungs in the Soviet hierarchy, meaning that each was the titular people of an autonomous republic. The Volga Tatars of the Tatar Autonomous Soviet Socialist Republic (TASSR) were incorporated into the USSR on May 27th 1920 and the Chechens of the Chechen-Ingush Autonomous Soviet Socialist Republic (CIASSR) were incorporated on December 5th 1936. However, the trajectory of the Post-Soviet transition has resulted in very different outcomes for these two peoples. In Chechnya, the transition brought to power General Dzhokhar Dudaev, a radical separatist, who did not flinch from the prospect of war with Russia. On the other hand, Tatarstan won substantial autonomy from Russia without using violence. This paper aims to answer the question: why did these outcomes diverge so drastically? This question can be answered in various ways. In the first chapter, I will address the basic geographic and demographic differences between the two societies. In the second chapter, I will explore the differences in the long-term historical experiences among the Volga Tatars and Chechens and the impacts the Tsarist Empire and Soviet Union had on their respective societies. In the third chapter, I will examine Russia’s insecurities regarding its level of civilization and their efforts to “orientalize” the Caucasus as a means of better defining Russian identity. I will use Edward Said’s Orientalism as a theoretical lens of analysis. In the fourth chapter, I will outline the differences between the two republic’s political developments in post-Soviet transition and the vital distinctions in the democratic processes. In this section, religion and its role in each society’s respective politics will become apparent. In the final chapter, the aftermath of the two wars with Chechnya will be examined and the correlated socio-economic problems as well as the contrasting socio-economic situation in Tatarstan today. In this section I will specifically stress the significance of the Kadyrov family on modern day Chechnya and prospects for the future.