W.E. Gladstone's changing and inconsistent views on religious oaths and established churches present an intriguing puzzle. This article compares and contrasts his early and later stances on these topics with the purpose of evaluating the place of practical judgments in his arguments. This exploration reveals that the prevailing description of Gladstone's views, which privileges the role practicality played in his later support for a more liberal set of policies governing church-state relations, does not explain the changes and inconsistencies in his position as well as does a description that emphasizes the changes and continuities in his fundamental philosophy. In conclusion, connections are suggested between this explanation of Gladstone's views and theoretical considerations regarding the development of liberal freedoms.