Death takes a prominent place in the writings of Paul. His gospel offers the solution for death as sin's consequence—Jesus' death and resurrection provides propitiation, reconciliation, and eternal life. In spite of this confidence, however, he speaks about death often, at times affirms that he anticipates death with a positive attitude, and speaks of dying voluntarily. Paul was aware of his mortality and he lived and ministered out of this awareness. The thesis of this dissertation is that Paul uses expressions of mortality in terms of imitating Christ with three distinct senses or paradoxes based on the occasion into which he was writing. To churches with those who opposed him or his gospel, he spoke of noble death with an honor/shame paradox. To churches that were facing persecution, he spoke of martyrdom with an obedience/defiance paradox. To churches and colleagues who grasped the atoning nature of Christ's death and its implication within God's redemptive plan, he spoke of a life/sacrifice paradox. This dissertation examines Paul's theology of death and mortality by looking at semantics, background influences, then Paul's teaching and example. We begin in chapter two by defining the terminology of voluntary death. Chapters three to six discuss the major worldviews from which Paul drew his theology: Gentile, Jewish, the influence of Jesus and the early church. Chapter seven discusses Paul as a historian and theologian and engages his writings with a view to better understanding his positive affirmations of death in light of his ambition to imitate Christ and to lead others to follow his example.