International investment treaty law and arbitration is a field that is fraught with conflict. Arising out of the post-Cold War geopolitical environment, states in both the Northern and Southern hemispheres have signed onto muscular legal constraints that protect foreign investors. Measures that diminish the value of an investment and that run afoul of protections associated with classical property, contract, and due process rights entitle investors to sue for damages before privatized dispute resolution panels. An investment arbitration community has blossomed alongside the spread of investment treaty disciplines. Among its constituent members are teachers who write, advise, and take part in the field of international investment arbitration, both inside and outside of universities. Taking my cue from the work of Max Weber, this chapter describes these teachers as “charismatic educators” who offer leadership via legal education as a means of training and recruiting newer generations who will fight on behalf of investment law’s ideals. In performing this function, they offer justifications for the regime by having recourse to their own authority and expertise. We learn that legal educators play a substantial role in the upkeep of investment law’s machinery while maintaining an intimate relationship to its practice.