When the Penitent Surpasses the Righteous: The Deeper Truth About Spiritual Growth

Yoav asks: "Shalom. There’s something that’s been on my mind lately. They say that in the place where ba’alei teshuva (penitents) stand, even complete tzaddikim (righteous people) cannot stand. And that with tzaddikim, Hashem is exacting with them even to a hair’s breadth.

• Why one should strive to be a tzaddik, if it seems better to be a ba’al teshuva and merit a higher level in Gan Eden?

• Why is it worthwhile to be a tzaddik if God scrutinizes them so strictly, and in the end, they don’t even reach the level of ba’alei teshuva? I know this can’t be right, but I can’t figure out where the mistake lies.

• Why is it said that God desires the prayers of tzaddikim and gives them suffering for this purpose? After all, they’re not guilty."

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Shalom Yoav, and thank you for these thoughtful questions.

Firstly, even tzaddikim do teshuva, for as it says, “For there is no man so righteous on earth who does only good and never sins” (Ecclesiastes 7:20). Everyone repents — even the greatest tzaddikim, as part of their continual growth in Torah and mitzvot. The verse also says, “For a tzaddik falls seven times and rises again” (Proverbs 24:16); he’s called a tzaddik not because he never falls, but because he keeps getting up without giving up.

The Talmudic statement is: “In the place where ba’alei teshuva stand, complete tzaddikim cannot stand” (Sanhedrin 99a), but as we see, some tzaddikim are also ba’alei teshuva, and some ba’alei teshuva become tzaddikim. The boundary isn’t always obvious. Rabbeinu Bachya in Chovot HaLevavot (Sha’ar HaTeshuva, ch. 8) clarifies by dividing ba’alei teshuva into three categories:

1. The first type: A tzaddik who never transgressed severe sins (karet-level), but may have occasionally neglected positive mitzvot (e.g., missed tefillin, improper lulav intentions). Once he repents, all is forgiven and he is a complete tzaddik.

2. The second type: One who violated prohibitions but not those punishable by karet or death (e.g., shaving with a razor, eating non-kosher). Upon repentance, he rises to a level above a complete tzaddik because his past mistakes now humble him, giving him greater humility. This is the level referred to in the statement that tzaddikim cannot stand in their place.

3. The third type: One who committed severe sins (karet/death penalty) such as forbidden relations or Shabbat desecration. Repentance cleanses him, but due to the gravity of his sins, he needs further purification through suffering and trials. He becomes righteous, but not necessarily on the same elevated plane as the previous category.

It’s Never “Better” to Sin

God created us to fulfill His mitzvot, not to break them and then fix them. The purpose is to live without sinning. The Sages warned: “One who says: I will sin and then repent… is not given the opportunity to repent” (Mishnah Yoma 8:9). We therefore pray daily: “Do not bring me to sin… nor to trial.”

The unique level of a ba’al teshuva is, in a way, “affirmative action” for spiritual recovery by helping the fallen rise. It’s not an incentive to fall. God grants this special status out of mercy so they won’t remain spiritually crippled forever.

How Rambam Explains It

Rambam (Hilchot Teshuva 7:4) writes that ba’alei teshuva are beloved like those who never sinned — and sometimes more, because they’ve tasted sin, abandoned it, and conquered their desires. This struggle, and the pain of change, earns them a reward even tzaddikim might not receive. Still, the Rambam’s words are intended to encourage penitents, not to suggest one should sin to gain advantage.

Special Rewards for Different Trials

Think of Gan Eden as containing countless “treasuries” of reward, each tied to specific spiritual achievements, such as enduring insults without retaliation, resisting temptations, persevering in learning Torah, etc. Ba’alei teshuva have their own treasury for overcoming their specific challenges, but the greatest treasury of all is reserved for Torah study and mitzvah observance from the start.

The ultimate goal is threfore to be a tzaddik, and great ba’alei teshuva strive to become tzaddikim through Torah and mitzvot.

Why God Tests Tzaddikim

The strict “hair’s breadth” judgment of tzaddikim isn’t punishment but opportunity. Greater trials mean greater eternal reward, like a general sent on a crucial mission, not a punishment detail. Some tzaddikim, like Rabbi Akiva, even yearned for such tests to fulfill “with all your soul” — loving God even unto death.

When the Midrash says “God desires the prayers of the righteous” (Bereishit Rabbah 45:4), it refers to these exceptional souls whose prayers can benefit the entire generation. Their trials create heartfelt prayer that sustains the world.

Ba’alei teshuva and tzaddikim each have unique spiritual roles and rewards. God never intends sin as a path to greatness. The highest goal remains to be a tzaddik, close to Him through Torah and mitzvot, accepting all life’s trials as opportunities for eternal elevation.