The focus of this chapter is Giannicola di Paolo, a Perugian native who worked as a collaborator to Perugino (and perhaps also to Pintoricchio) in the generation before Raphael prior to embarking on his own lengthy career. An analysis of the life, major works, and workshop of this incredibly well-documented artist provides valuable insights toward our understanding of a successful local painter who was also active in Florence and Rome and was commissioned by ecclesiastic, civic, and private entities.