The author contends that Augustine maintained a salvation-centered view of the human will, while Aquinas tended to be more optimistic on human nature and the freedom of choice per se. Augustine took human will for free so long as any choice is made as a result of personal volition without duress. However, the author shows that, for Augustine, the so-called freedom stands for the status of salvation which has God as its goal, an existential restoration. Since the goal of such ultimate salvation is beyond human capability, and in light of the fact that human destiny hangs uncertainly in relation to the almighty and omniscient God, it is unconvincing to equate the exercise of personal volition with freedom. The author also questions the wisdom of making distinction between foreknowledge and predestination, as it appears in the Augustinian tradition and is repeated in Aquinas’s idea. The distinction attempts to justify the claim that what God foreknows would not intervene the freedom of the will, on the ground that what is foreknown is being played out unforcefully according to the divine mega plan. This attempt fails to account for what the predestination implies for the human status in regard to the saving grace and the ultimate fate. Aquinas affirms the practical function of the human will in fulfilling an ethical life. The will comes under the guidance of the intellect, while at the same time affecting the intellect by its determination. God is the first and final cause of all creatures, yet His providence and predestination are not part of the nature of the created will, and would not negatively undermine its power. Metaphysically speaking, Aquinas’s model of the ladder of created beings which envisions a static cosmos, along with his adoption of the Aristotelian hylomorphism, can work to accommodate the active role of created will in the dynamic change of human condition, for better or for worse. Although this accommodation acknowledges the superiority of a transcendental design, the author finds it an unsatisfactory solution to the seemingly overriding power of the providential mind. In the final analysis, the author admits that freedom means being free not to sin. Only by a living faith in the truth of revelation can the created will experience such freedom.