In Chapters of the Fathers (Pirkei Avot 2,18) we learn the words of R. Shimon ben Netanel (Rshb"n, mentioned beforehand in Mishna 10):

When you pray, do not perform your prayers by rote, but rather render them [an appeal for] mercy and grace before G-d, as is written: "For He is gracious and full of mercy, slow to anger, abundant in kindness, and relenting of the evil decree"(Joel 2,13).

This teaching appears to parallel very closely a teaching by R. Eliezer in another Mishna (B'rachot 4,4): "One who renders his prayers by rote, it is not [an appeal for] mercy."

However, there is a big difference between them: Rshb"n added a verse to prove his point.

But this is very puzzling: What proof is there in the verse from Joel regarding Rshb"n's teaching? The verse speaks of one who did t'shuvah, repentance, whereas Rshb"n was speaking about prayer!

The explanation is this: In the above-cited Mishna 10, Rshb"n was specifically commended as one whose outstanding quality was "fear of sin." That is, he was always replete with fear of sin – even when he prayed. His prayer was one of "fear of sin," which necessarily results in t'shuvah – and that is why he cited, in his teaching about prayer, a verse having to do with t'shuvah.

That is to say: Rshb"n wished to teach us that our prayers must stem from t'shuvah. After one does t'shvuah, all of his good deeds and his mitzvah-actions take on a new light. We see this in the classic work by Rabbeinu Yonah entitled Shaarei T'shuvah (The Gates of Repentance). Its first two "gates" deal with t'shuvah, followed by a section on mitzvot that seem to have nothing to do with t'shuvah. Why is this? Because after a person does t'shuvah, all of his mitzvot receive new meaning.

The same is true for prayer: Once one is engaged in t'shuvah, his prayer is different; it is powered by t'shuvah, and is lit up in the light of t'shuvah. Rshb"n comes to teach us that our prayers must always be of that type – and that is why he cites the verse from Joel.

The Rambam (Maimonides) speaks precisely of this type of prayer. He writes that "one of the ways of t'shuvah is for the returnee to cry out always before G-d." This is actually a novel thought of the Rambam, for we don't find that he holds that there is a special prayer of t'shuvah.

To elaborate on this point: We know that the Rambam and the Ramban (Nachmanides) have a fundamental disagreement on the obligation of prayer. The latter holds that the Torah obligation is to pray during times of trouble, such as, "When there is war in your land, against an enemy who oppresses you…" (Bamidbar 10,9), and as King Shlomo explained (Kings I 8, 33-39). Thus, the Ramban maintains that the mitzvah of prayer is reserved for times of trouble, when one must do t'shuvah and pray that the evil decree be rescinded and that his sins be forgiven.

However, the Rambam's approach is that any type of prayer is a daily Biblical obligation, and there is no need for a special Torah directive to pray specifically when we are in trouble – for we must pray in any event. We therefore would not have thought that there was a special prayer for or about t'shuvah – but when the Rambam tells us that "crying out" is one of the "ways of t'shuvah, this is a great lesson for us regarding his view of the concept of prayer.

In sum: There is a special obligation to pray amid and with t'shuvah - and just like any other mitzvah, prayer that is done in this way is on a much higher level than other prayer.

Translated by Hillel Fendel