Throughout history, both philosophers and non-philosophers have doubted that philosophical positions qua philosophical positions are justified and that philosophy is a rational enterprise. Today, such doubts are grouped under the term “Metaphilosophical Skepticism”. Nicholas Rescher, in his book Strife of Systems, includes Kant among the proponents of this kind of skepticism. I want to argue that while Rescher is wrong, Kant has con­tributed to a new version of such skepticism. In the first step, I characterize the basic idea of metaphilosophical (...) skepticism in more detail and identify a version of this idea, which I call “Second-Stage-Skepticism” and on which I will focus. In the following part, I reconstruct Rescher’s reading of Second-Stage-Skepticism as well as his reasons for considering Kant to represent this version. My main claim in this part will be that there is no reading of the mentioned basic idea that makes Rescher’s view reasonable. In the third step, I introduce a newer form of metaphilosophical skepticism — “Third-Stage Skepticism” — and conjecture that this form can be seen as inspired by Kant’s thought on philosophical diversity. Finally, I point out a way to reject this newer form. (shrink)