The Prisoner Who Refused Tefillin: A Lesson on Repentance and Trust in God

In the book Ish Tzadik Haya (“A Tzaddik in Our Time”), about Rabbi Aryeh Levin, we read a moving story that reveals both his gentleness and his uncompromising dedication to Torah and mitzvot.

Rabbi Aryeh was known for visiting prisoners and offering them encouragement. During one such encounter, he gently began guiding an inmate toward keeping Torah and mitzvot. Because of Rabbi Aryeh’s extraordinary sensitivity and kindness, the prisoner readily agreed to accept everything upon himself, except one commandment of putting on tefillin (phylacteries).

The prisoner said: “Anything you tell me I will do — even the most difficult commandments, but not tefillin.”

Rabbi Aryeh was astonished. Why would this be the one mitzvah he refused? He asked him why tefillin, of all things, felt impossible. The prisoner explained with deep pain: “I am here in prison because I murdered my wife. How can I dare place holy tefillin on the very hand that took a life?”

The Torah’s Perspective: Is a Murderer Exempt from Tefillin?

This may seem logical to human reasoning, but what does the Torah say? Does a murderer become exempt from tefillin? The answer is absolutely not.

On the contrary, if a person does not correct his misdeeds now, then when will he? We live in a world of tikkun (repair). In His love, the Creator has given humanity the gift of repentance, offering even the gravest sinner a path to return. As Rabbeinu Yonah wrote, no sin blocks a person from coming back.

The Torah declares: “He has not beheld iniquity in Jacob, nor seen perverseness in Israel; the Lord his God is with him, and the King’s friendship is in him.” (Bamidbar 23:21)

Rashi explains: God does not fix His gaze upon the Jewish People's sins with exacting scrutiny. Even when they anger Him and rebel, His love remains. The phrase “the King’s friendship is in him” expresses affection and closeness.

Divine Love Despite Rebellion

The Midrash (Bamidbar Rabbah 20:16) provides a striking parable. Normally, a legion that rebels against its king is punished with death. However, the Jewish People, even after rebelling and declaring at the Golden Calf, “These are your gods, O Israel,” were not annihilated. Even then, God’s love never left them.

We know the Creator is not indulgent. The Talmud (Bava Kamma 50a) teaches that God judges every detail of our actions. How then can Scripture say He “does not look upon iniquity”?

The Nesivos Shalom who was the Rebbe of Slonim explains that when a Jew sins but his heart is broken and heavy because he knows he has stumbled, then God has mercy. He lengthens His patience, waiting for the sinner to awaken and return.

This is the deeper meaning of the verse: “He has not beheld iniquity in Jacob.” God does not scrutinize the sins of one who, even while sinning, feels brokenhearted and remembers his Creator. Such a person, though fallen, is still accompanied by the King’s love.

Even in Sin: “Know Him in All Your Ways”

The Talmud (Berachot 63a) records Bar Kappara’s teaching: the small verse that contains the whole Torah is “In all your ways, know Him, and He will direct your paths” (Mishlei 3:6). Rava adds: this applies even in the moment of sin.

The Ein Yaakov version quotes Rav Papa: “That is why people say that even a thief digging a tunnel prays to God for help.”

Initially this seems absurd. How can one pray to God in the very act of wrongdoing? The message is that even when the yetzer hara (evil impulse) overpowers a person, he should remember that God sees him. If his heart is broken in that moment, he can turn it into an opportunity to call out to God, begging for strength to change.

Trust in God as a Loving Father

The essence of Jewish faith is bitachon (trust in God). As the Vilna Gaon taught, the purpose of mitzvot is to build trust in our Creator. Rabbeinu Yonah (Mishlei 3) explained that one must hope in God always, even in the darkest times when no salvation seems possible.

Relating to God only as a King makes trust difficult. A distant monarch may not concern Himself with a struggling subject, especially one who has broken the law. If however one sees God as a loving Father, the picture changes completely. A father always rushes to help his child, even if that child has gone astray.

The Mishnah (Sanhedrin 6:5) teaches that when a person suffers, even a sinner, the Divine Presence cries out in pain: “My head hurts, My arm hurts.” God shares in our pain like a compassionate parent.

Thus, even the sinner can trust in God. The verse (Tehillim 32:10) says: “Many are the sorrows of the wicked, but one who trusts in the Lord, lovingkindness surrounds him.” The Sages emphasize that even a wicked person who trusts in God will be surrounded by mercy.

God Does Not Overlook, But He Waits

God does not overlook sin without consequence. As the Talmud says, anyone who claims God is indulgent will find their life cut short.

However, His refusal to “overlook” is itself mercy. Overlooking would mean dismissing our actions as if they didn’t matter, leaving us in spiritual poverty. Instead, God gives us the gift of teshuvah (repentance). He wants us to use our failures as opportunities to grow, to rise again like champions.

Even the thief who prays while stealing is, at some level, acknowledging God. His cry — “Lord, I know my actions are wrong, but please be patient with me until I repent”, is misguided, yet it demonstrates that he has not severed his bond with God.

This extreme example teaches that there is no circumstance in which a person is cut off from hope. Trust in God remains possible even in the lowest places, because He is not only King of the universe but also our Father, whose love and patience extend to all His children.

No sin, however great, disqualifies a person from reconnecting with God. Trusting Him, even in brokenness, draws down mercy and creates the possibility of change.