The answer lies in the nature of sin. As I understand the Thomist and Augustinian notion, evil is not a positive force but an absence, a nonbeing, as cold as the absence of heat energy or dark as the absence of light energy. In this theological idea of privation, a practicular sin or evil is a place wehre the moral energy of God's creation is withdrawn, or shriveled away, or destroyed. The sin is a dead place in the soul, a hole or area of absolute zero, just as Hell is a place of dark and cold.
The sin is a wound that hurts, and it is, moreover, a self-inflicted wound. The idea of privation, with its corollary that sin is a place where the soul has torn part of itself away, reminds me of a saying I have heard quoted in the Talmud, to the effect that the evils of others do to us are as nothing compared to teh evils we do to ourselves. The remarkable fact is that for most people (excepting, for example, victims of oppression, torture, famine, disease), this is true. We wound ourselves, and that fact is one of the great moral mysteries.
.... the idea of wanhope or despair: the fatal sin that keeps the soul from praying sincerely for grace. Though mercy is infinite, the soul succumbs to fear: it believes it is too fallen or corrupt to be saved.
Peter S. Hawkins and Rachel Jacoff (ed), The Poets' Dante
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