This article joins others in assessing the role of Christ in the moral theology of Thomas Aquinas. It investigates one specific phrase in the Summa Theologiae in four stages. First, there are some foundational considerations of Aquinas's overall framework. Second, I examine the evidence supporting Aquinas's original description of Jesus as our ‘dearest friend’ and as further disclosed in the Tertia Pars, specifically in His Passion and in His role as Teacher. Third, this leads to a consideration of Jesus as ‘wisest’ as the Incarnate Word and Wisdom. Fourth, I probe this sapiential aspect further in terms of the gifts of the Holy Spirit, specifically, that of wisdom, and, in particular, as construed in recent work on the second person perspective and Joint Attention. By investigating this phrase of Aquinas, it emerges that its sapiential, soteriological and inter-personal character is illuminated further by its Christological and ecclesial dimensions.