In this study, John-Paul Harper critically compares how Paul and Philo rethought the significant Jewish symbols of Land, Jerusalem, and Temple. Drawing particular attention to their political significance, he demonstrates how these symbols offer important insights into how both Paul and Philo conceptualised authority in the local community (Temple), within the wider people of God (Jerusalem), and in relation to the Roman Empire (Land). The author argues that, while both conceptualised authority in charismatic terms, Philo’s appropriation tended to be more individualistic and focussed on otherworldly realities, whereas Paul’s tended to be more communal and focussed on this-worldly realities. Along the way, the author contributes to contemporary discussions of Paul and Philo’s Jewish identity, their perspectives on community leadership and order, and their perspectives on the Roman Empire.