(Anselm 110)
It appears that Anselm is ultimately equating free will with uprightness-of-will, for he argues that there is nothing -- even God -- which can separate the will from its essential uprightness:
Indeed, although He can reduce to nothing an entire substance which He has created from nothing, He is not able to separate uprightness from a will which has it... If God were to remove (the oft-mentioned) uprightness from someone, he would not will him to will what He wills him to will. (Anselm 119)
Anselm begins from the proposition that God is good, upright, just, and that nothing can flow from Him which does not have these qualities. Free will is a gift to man from God and is therefore inherently a good thing. Even God cannot undo the goodness which is at the heart of free will, His own gift. In terms of the relationship between divine grace and free will, Anselm writes that divine grace is a power which transcends free will:.".. Divine Scripture sometimes speaks in such a way that only grace -- and not at all free choice -- seems to avail to salvation" (Anselm 199). On the other hand, Anselm cites a number of passages from Scripture indicating that "our entire salvation were dependent upon our free will" (Anselm 199).
Anselm's intent is to counter those who would argue that either our salvation depends entirely on our free will or our salvation depends entirely on divine grace:
My intention will be to show that free choice coexists with grace and cooperates with it in many respects -- just as we found it to be compatible with foreknowledge and with predestination. (Anselm 200)
Anselm approaches his subject to applying the workings of human reason to the mysteries of God's will. In his time, the activities of philosophers and theologians were beginning to meld together, and Anselm was one of the Christian thinkers who believed that such a melding was a good thing. He was not attempting so much as to discover the truth from scratch; rather, he was trying to take the received truth from the Bible and to apply reason to those truths in order to turn them into rational realities rather than mysteries of a divine realm accessible only through faith. To accomplish this, Anselm can be expected at every turn to have some rational explanation which would allow man to see himself as both bound to God's will and yet able to exercise some sort of free will at the same time. Such free will must flow from God in order to be a force for good in man's life. At the same time, it is clear that man must be shown to have some sort of independent liberty in the enterprise at hand if he is to be seen as something other than a slave to God's will. Indeed, if man is seen as such a slave, then all is predestined, all is predetermined, and there is nothing outside of that well-laid-out and unchangeable plan.
Anselm's philosophy is "predetermined" at least to the extent that he will at no point throw up his hands and admit that he simply does not know the answer to any question which is put to him about free will, divine grace, predestination, and so on. Anselm's philosophy must be understood in the context in which it is presented, and in this way Anselm shows a predisposition toward each of the matters with which he deals and toward the theoretical analysis he performs in order to support his conclusions.
For example, there would be little benefit for Anselm to consider that there is no relationship between divine grace and free will, or that there is no cooperation between the two. Remember, Anselm was not merely engaging in a leisurely philosophical pursuit in order to entertain the idea that Christianity was a rational discourse. Rational philosophy was first seen as a threat to Christianity, but Augustine and Aquinas and Anselm used philosophy as another tool to convince others that Christianity was true and should be followed as a way of life. Therefore, it would not do for Anselm to admit that he simply did not know the answer to any questions about God, for this would throw the questioner into doubt about the truth of Christianity. It also would not do to separate philosophically the free will of man and the grace of God, for that would leave the listener or...
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