This study focuses on Kant's attempt to find the link between feeling and cognition on a priori grounds in the three Critiques to make philosophical judgment possible. As such it treats the area of aesthetics and its formal principles. This work explores the enigma: How is it that Kant values the talent to judge more than understanding and reason; indeed the lack of it «no school can make good». Yet, even though Kant demonstrates how a priori synthetic judgments and a priori moral judgments are possible as particular pronouncements, he analyzes the power of judgment itself as an independent faculty only in the last Critique. The author argues that the aesthetic factor plays a recalcitrant, yet vital and necessary role in all human judging. Finding an adequate niche for feeling and its a priori principles becomes a key problem not just for Kant but for the entire philosophical enterprise.