This article undertakes a comprehensive and thematically integrated examination of the tension between pastoral vocation and entrepreneurial engagement among Catholic priests in Nigeria, analyzed through the juridical framework of Canon 286 of the 1983 Code of Canon Law, which prohibits clerics from conducting business or trade for personal profit without the explicit authorization of legitimate ecclesiastical authority. The analysis proceeds through a carefully sequenced argument that moves from the historical foundations of clerical economic discipline, through theological anthropology and African communal philosophy, canonical and comparative ecumenical analysis, documented patterns of canonical abuse and practical clerical experience in Nigeria, episcopal governance and institutional responses, and finally toward proposals for contextualized canonical reform. This article argues that clerical entrepreneurship in Nigeria must be understood not as a straightforward act of canonical disobedience but as a structurally generated convergence of institutional insufficiency, communal obligation, political economic failure, and the cultural authority of prosperity theology within the Nigeria religious landscape. Drawing from the patristic sources, conciliar documents, the canonical tradition from Gratian through the 1983 Code, African philosophical anthropology, and a sustained body of empirical ecclesiological scholarship on the Nigerian Church, the article proposes a contextualized canonical hermeneutic grounded in the classical principle of epikeia, the theology of reciprocal canonical obligations, and the social teaching of the Church. The article concludes that the canonical future of clerical economic engagement in Nigeria depends upon willingness of the episcopate to exercise contextually sensitive leadership, to reform diocesan financial structures, and to preserve the prophetic integrity of ordained ministry against the seductions of a market culture that has penetrated the Church’s own institutional life.