This thesis submits Luigi Giussani’s theological writings to philosophical analysis. Giussani (born in Desio, 1922; died in Milan, 2005) was a prominent Italian author, public intellectual, university lecturer, and founder of the international Catholic lay movement Communion and Liberation (CL). My enquiry is motivated by the experience of readers who find Giussani’s texts marked by vagueness and seeming inconsistencies despite his attempt to respond decisively and sensitively to real human problems. It also presents ideas from those works available only in Italian to an English-language readership for the first time. Rather than criticize the author’s style of exposition, or restate his arguments in a manner more suited to my audience, I treat the texts’ burdens as symptomatic of the author’s deeper, unarticulated concerns. I reconstruct Giussani’s implicit concerns using history, intellectual biography, sources, and the logic of enquiry itself. I then re-read his texts in the light of the explicit rendering of those concerns and, where the texts’ burdens still persist, I suggest repairs corresponding to those concerns and to the errant behaviours his writings were generated to correct. Three themes are examined: judgement, freedom, and beauty. These were prominent in Giussani’s dialogue with students from the 1950s onward and integral to his idea of the religious education of youth. My analysis is conceived as a contribution to philosophical theology, rather than to the philosophy of education. The areas flagged for repair, however, may nonetheless serve educators. I conclude that Giussani’s account is indeed shaped by his implicit concerns; that their nature provokes the essentialist arguments he mounts; and that his attempt to expound intrinsic, universal, and timeless claims runs against the pragmatic thrust of his writing. My repairs call for a better account of 1) practical deliberation, 2) discursive reason, 3) obedience in relation to autonomy, and 4) habits related to the formation of virtues. I argue that the practical grounds of his project are best anchored in robust solutions to the problems of ordinary life formulated from the deepest sources of repair from Giussani’s tradition (sacred scripture and sacred tradition, including the liturgy) rather than what he calls the “needs and exigencies of the heart,” which address a different problem (namely Enlightenment rationality or Neo-Thomism).