My friend and I are having a disagreement about degrees of righteousness in God's eyes. Who is greater: One who is virtuous by inclination, or one who is virtuous by choice - i.e. one who must struggle with his passions and transform vice into virtue?
The Aish Rabbi Replies
The Talmud says: "In a place where a ba'al teshuva (spiritual returnee) stands, even a full tzaddik cannot stand" (Brachot 34b). The idea is that by having sunk to the lowest depths, and then genuinely turning one's life around, the distance traveled in a positive direction is so great that it even exceeds those who have always been on the plus-side.
(Of course, one would not want to deliberately get into a negative situation, because there is no guarantee of coming out. Further, it often leaves residual stains.)
The great Mishnah commentary, Tifferet Yisrael (Kiddushin 4:14), tells of a fascinating event in the life of Moses:
An Arabian king sent an artist to the Israelite camp with orders to paint a portrait of Moses and to return with it to Arabia. (Those were the days before digital cameras.) Upon receiving the portrait, the king's physiognomists prepared a "face-reading" analysis of Moses to determine the base nature of Moses' personality. The ensuing report described Moses as greedy and arrogant. The king rebuked his physiognomists for their patently absurd analysis, given Moses' sterling reputation for kindness and humility.
The king decided to resolve the matter by visiting the Israelite camp and relating to Moses all that transpired. Moses assured the king that the physiognomists were as competent as the artist. Moses explained that by inclination he had many character flaws. Only sustained self-discipline and sheer determination enabled him to overcome his natural inclination and to obtain the stature and glory that were now his.
I should mention that various rabbis doubt this story, given the other sources that Moses was righteous from birth. But the idea is valid: Through sheer determination, we can overcome our flaws and achieve great spiritual heights.