This study explains how one of the most remarkable thinkers of the Italian Renaissance, Giovanni Pico della Mirandola (1463–1494), broke new ground by engaging with the scholastic tradition while maintaining his ‘humanist’ sensibilities. A central claim of the monograph is that Pico was a 'philosopher at the crossroads,' whose sophisticated reading of numerous scholastic thinkers enabled him to advance a different conception of philosophy. The scholastic background to Pico’s work has been neglected by historians of the period. This omission has served to create not only an unreliable picture of Pico’s thought, but also a more general ignorance of the dynamism of scholastic thought in late fifteenth-century Italy. The author argues that these deficiencies of modern scholarship stand in need of correction.