The effects of transformations in the cultural context on the structures of the Catholic organization and consequently on the identity and role of priests is explored in this research. The way these transformations affect clergy relationships with the church, diocesan authorities and parishioners, and ultimately the psychological wellbeing of priests, are investigated in the light of recent research and literature. Quantitative and qualitative data from the Catholic Church Life Surveys (CCLS) of 1996 and 2001 is analyzed, together with qualitative data generated through semi-structured interviews. The theoretical underpinning for the interpretation of changing clerical identity and roles and the relationship dynamics is personality theory, including a neoanalytic model (Horney, 1950), and a psychodynamic approach using an iconic reading of Freud (Cozzens, 2000). Social identity theory (Haslam, 2001), and Fowler’s (1996) theory of faith development also contribute to the theoretical framework. The NEO-FFI personality factors (Costa & McCrae, 1992) are used as covariates throughout the analysis. Four major themes are addressed in this research. First, ambiguities in the identity and role of clergy brought about through structural changes in the organization following the Second Vatican Council. Second, cultural changes which challenged the institutional hierarchical structure of the church and some of its theological and ecclesiological positions. Third, the contribution to satisfaction with ministry and personal wellbeing made by priests’ relationships with the organization, diocesan authorities, and parishioners, as well as intimacy with colleagues and friends. Finally, the impact of psychodynamic factors on the spiritual and psychological dimensions of priestly life. It was found that although the sacramental role of priests remains largely intact, their identity as religious and spiritual leaders is under challenge through greater participation in parish life by educated and theologically trained lay people. It is argued that the competence to appropriately express leadership, preach meaningful homilies and promote spiritual growth in parishioners rests on the attainment of mature psychological development and continued faith and spiritual formation. Analysis of personality factors showed that sound organizational and structural supports are needed to assist priests in their personal and professional lives. Over half the priests in the present study were found to be vulnerable to emotional and psychological distress, while others had strong resources to cope with increased ambiguity and complexity in ministry. A review of literature suggests that cultural changes over the last 30 years compound the effects of Vatican II, particularly the patriarchal hierarchical structure of the organisation and teachings on sexual morality that are under pressure from changing attitudes by both clergy and laity. Quantitative and qualitative analyses showed that there is little support by priests for the obligation of celibacy, the successful attainment of which demands a high level of mature psychosexual development. It was argued that without a strong clerical commitment to celibacy, education and training programs currently being implemented in seminaries would be largely ineffectual. Key factors impacting on the relationships of priests with parishioners were found to be first, a decline in the authority of priests, second, the revelations of sexual abuse by priests, and third, the difficulty numbers of clergy have with establishing and maintaining close, intimate relationships. The NEO-FFI factors Neuroticism, Extraversion, and Agreeableness were found to be significant predictors in the quality of relationships between priests and parishioners, with 30% of clergy experiencing difficulty in these relationships. It was argued that maturity in spiritual, psychological, and psychosexual development was found to impact significantly on clergy personal wellbeing and professional competence, which in turn contributes to satisfaction with ministry.