Freedom Puzzle

I started reading Augustine's "On the Free Choice of the Will" on a crowded "combi" (Peruvian bus) yesterday. This part puzzles me:

"All wicked people, just like good people, desire to live without fear. The difference is that the good, desiring this, turn their love away from things that cannot be possessed without the fear of losing them." (1.4)

To untangle that, I thought of an example; a wicked man chases after money, but money, as it is essentially a tool for exchange, is something he is likely to lose (and given our current economic situation I think we Americans can agree on this assumption). So the man who loves money shows intemperate desire and it is intemperate because it's a risky kind of love. This sounds a little Stoic to me. Now imagine loving something which is impossible to lose. We cannot imagine this well in light of the fact that we all die... But say a good person loves her child and is promised by some omniscient source that she will never lose that child. She might not guard her child in public places like most parents or be protective of her in her teenage years.

It seems that loving involves risk when it is a deep sort of loving. And that risk seems to come from attaching ourselves to something outside ourselves- something over which we have no control. But if we are certain that we will never lose the object of our love, i.e. that we will always possess it, that surely we are in control of that which we possess. Risk is eliminated.

Imagine God loving mortal souls He could not lose. In no way do I think that God is attached to us in a way as though He's in need of us or something we possess. But I do think He willfully put Himself at risk of losing a "beloved" in making us the sort of free beings that can run to or away from Him. And I wouldn't want Him to do it any other way; His love for me, in fact, astounds me more because He so loves me and my fellow wandering creatures that He "cries" at the loss of one of us.

But this leads me back to the question of death and whether values that are specifically mortal (essentially lose-able) are of a sort which cannot be had if they cannot be lost in death. If I want to acknowledge immortal values as having worth that surpasses mortal values, then here I have to concede that love of something we will not lose is good and the love of something we might lose is worse.