The aim of this paper is to expose the intimate relationship between deep disagreements and skepticism. Philosophers have explored how deep disagreements lead to skepticism about their resolution at the metalevel (about whether one knows that P), but they have paid little attention to how they also lead to first- or object-level skepticism (about whether P is the case) and how skepticism also produces deep disagreements. I show how engaging in a discussion about any topic against a radical skeptic position always leads to deep disagreement. Furthermore, the disagreement engendered by radical skepticism is a kind of deep disagreement at the level of epistemic evaluation of propositions that covaries with deep disagreements at the object level. Deep disagreement and radical skepticism are intimately linked.