This paper aims at defining the specific negotiating subjectivity of a trickster that can be found in such bordering locales as the Caucasus and Central Asia, positioned in-between Europe and Asia on the one hand and Western modernity and Islam on the other hand. Being multiply colonized in an epistemic as well as economic and political sense, these regions have developed their specific strategies of survival, resistance to various regimes and, created hybrid, trans-cultural border models of thinking, that are still alive today and can constitute a way out of the contemporary dilemma—the Christian West versus Islam. The article traces the complex history of both locales in modernity, trying to understand the influence of those factors that turned them into the threatening images of paradigmatic anti-spaces, fallen out of time, for the West, and how Western modernization brought such foreign concepts to these territories as ethnic and linguistic nationalism, religious and linguistic purism and intolerance, that are the real threats today for the trans-cultural continuum of Central Asia and the Caucasus. A complicating factor in this case is that they were not directly colonized by the Western capitalist empires, but by the so called subaltern empires, like Russia, which was itself epistemically and culturally colonized by the West. Both the Caucasus and Central Asia were and are torn between the influences of the modernization via the Russian empire, via the Ottoman empire and sporadically directly by the West, but also both refuse(d) to make a final choice—instead they resort to the age-old tactic of balancing, of mediation, of a trans-cultural trickster type sensibility that gives them a lot of potential for the future. Another problem that is addressed in the article is that of Islam in the Caucasus and Central Asia (vis-à-vis ethnicity and nationalism) and the evolution of its interpretation by the Russian and Soviet imperial ideologues from relative tolerance to ethnicization, politicization and often demonization of Islam. The revival of specific forms of ethnic and territorial nationalism and in many cases Islamism in Central Asian or the newly independent states of the Southern Caucasus after the collapse of the Soviet Union are also addressed. In addition, there is the opposition of official cultural and political models of ethnic “etatism,” and the specific mediating border subjectivity of the people themselves which unexpectedly echoes the globalization flows of a rootless work force around the world, but which also presents a way out of the dead end of fundamentalism vs. neo-liberalism or the “clash of civilizations” model. These trans-cultural subjectivities and epistemologies can be expressed in many ways—from the “theology of liberation” to the ‘progressive Muslims project’, from other thinking to border thinking, but is always based on questioning the neo-liberal modernity from an in-between position. The Caucasus and Central Asia are close to this in the prevailing sensibility, being part of this global yet non-unified and lose movement of alternative critical and border thinking. What is needed is the development of coalitions and dialogue between such various border thinkers and trans-cultural multiply colonized locales on a global scale that would enable us to oppose both ethnic and religious fundamentalism and extremism of all shades and Western neo-liberal globalization as well.