This essence is based on his belief that free will an the freedom of choice which is the exercise of free will are rooted in "uprightness":
If freedom-of-choice had not been given to rational nature in order for it to keep uprightness-of-will for the same of this uprightness itself, then freedom would not have been conducive to justice, since it is evident that justice is uprightness-of-will for the sake of this uprightness itself. (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 reader with a terrible sense of alienation and isolation from God. At the same time, there were apparent contradictions between the various elements of the question (free will, predestination, divine grace, foreknowledge) which had to be resolved in order to put the minds and hearts of the questioning individual at ease. Of course, Anselm did not have all the answers to questions about God and man, and he was often thrown back on his faith, which may lead to circular definition, as in the following: "Absurdly, there is no doubt that the will wills rightly only because it is upright" (Anselm 201).
The basis of Anselm's rational philosophy of Christianity is that God is good and all things flow from God. When he moves from this grandest of assumptions to more subtle matters, Anselm often seems to be creating a contradictory structure. For instance, Anselm argues that a man cannot have uprightness-of-will from himself or from someone else; it can only come from God. To which he adds:
Thus, it follows that only by the grace of God does a creature have the uprightness which I have called uprightness-of-will. Now, I have shown that uprightness-of-will can be kept by free choice... Therefore, by the gift of God we have found that His grace harmonizes with free choice in order to save human beings. Thus, as happens in the case of infants, grace alone can save a human being... And in the case of those with understanding, grace always assists the natural free choice (which apart from grave is of no avail to salvation) by giving to the will the uprightness which it can keep by free choice. (Anselm 202)
It is difficult to imagine that one could go to Anselm in doubt about God, be subjected to this often-circular set of self-definitions, and come away in a more clear spiritual state, believing in God and one's relationship with God. To the contrary, it is easier to imagine that a person's reasoning powers would be beaten down by such a philosophy to the point that faith seems a simple respite from thought. We find the same problem when Anselm sets out to discover the relationship among foreknowledge, predestination, and free choice. With respect to foreknowledge and free choice, Anselm writes that it does not seem that God's foreknowledge of what a man is going to do and man's free choices are incompatible. He says that the two can somehow coexist, though, and he sets out to discover if this thesis is correct. Even before he begins his line of inquiry, though, the reader should see that Anselm simply cannot know what God knows or when he knows it. What he is doing is trying to use words to create a place of possibility wherein an individual can imagine that God's foreknowledge and man's free will are not incompatible. The fact is that they very well might be compatible in some divine sense to which human beings can have no access, even through reason.
To the individual who is about to choose a course of action, it seems confusing that God already knows what he is going to choose. Anselm can say that it is still a free act -- foreknown by God though it is -- because the actor is voluntarily performing the act, but it is undeniable that some of the luster of the freedom is eliminated by the fact that the outcome of the creature's willful considerations is foreknown. The reader might get the impression that Anselm himself is not completely persuaded by his own rationale:
Therefore, if these matters are carefully pondered, I think that no inconsistency prevents freedom of choice and God's foreknowledge from coexisting. (Anselm 183)
Anselm made important contributions to these arguments and set the pace for much of the discussion that would follow. He set a foundation on which others built their arguments, often without knowing the origin of this foundation.
Anselm. Anselm of Canterbury: Volume 2. Toronto: Edward…