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**Ramban's Letter to his son**

Commentaries used in this translation:
Rashi Commentary (1040-1105)
Rambam Commentary (1135-1204)
Rabbi Ovadiah of Bartenura Commentary (1445-1515)
Tiferet Yisrael commentary (1782–1860)
Rabeinu Yonah (1180-1263)
Derech Chaim - Maharal of Prague (1525-1609) (hebrewbooks.org/14193)
Biur HaGra of Rabbi Eliyahu of Vilna - (1720-1797)
Rabbi Avraham Azoulai commentary - (1570-1643)
Rabbi Chayim Yosef David Azoulai (Chida) commentary - (1724-1806)
Chatam Sofer commentary - (1762-1839), along with Ktav Sofer, and others
Ben Ish Chai commentary - (1835-1909)
and many more..

Commentary Level:
  • Min - (level 1) for basic commentaries as relating to the plain meaning (Pshat).
  • Med - (level 2) elaborates more into the theme.
  • Max - (level 3) deeper in, Maharal of Prague.
  • Max+ - (level 4) more themes in the text.
  • ShortMix - (recommended) short version of level 4.
Suggestion: Read once without commentaries (or min). Then a second time with.

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Chapter 2 Mishna 16פרק ב משנה טז
Rabbi Shimon said: Be careful with the reading of Shema and the prayer. And when you pray, do not make your prayers fixed but rather as [a plea for] mercy and a supplication before G-d, as the verse states, 'For gracious and merciful is He, slow to anger, abounding in kindness, and relenting of the evil [decree]' (Joel 2:13). And do not be wicked before yourself. רַבִּי שִׁמְעוֹן אוֹמֵר, הֱוֵי זָהִיר בִּקְרִיאַת שְׁמַע וּבַתְּפִלָּה. וּכְשֶׁאַתָּה מִתְפַּלֵּל, אַל תַּעַשׂ תְּפִלָּתְךָ קֶבַע, אֶלָּא רַחֲמִים וְתַחֲנוּנִים לִפְנֵי הַמָּקוֹם בָּרוּךְ הוּא, שֶׁנֶּאֱמַר (יואל ב) כִּי חַנּוּן וְרַחוּם הוּא אֶרֶךְ אַפַּיִם וְרַב חֶסֶד וְנִחָם עַל הָרָעָה. וְאַל תְּהִי רָשָׁע בִּפְנֵי עַצְמְךָ

Bartenura - "be careful with the Shema and prayer" - to read it in its proper time. Likewise for prayer, to pray each prayer in its proper time.
Rabbi Avraham Azoulai - Ahava b'Taanugim - he used the term zehirut (be careful) because in the morning, at the time of Shema and prayer, laziness strengthens over a man to not get up from his sleep. Thus he said "be careful" to push off the laziness from yourself and get up from your sleep..
Chida - Kisei David, drosh 18 - among the very first halachot in the shulchan arush is "Strengthen yourself like a lion to get up in the morning to serve your Creator..". Namely, fear of G-d at the beginning of the day, to get up in the morning and not miss the reciting of the Shemah in its time.. For if he begins by transgressing the first halacha in the Shulchan Aruch, he will go out from one evil to another, to miss prayer in a minyan, kadish, barchu, kedusha.. I don't want to say the severity of the matter so that people will not be mezid (more guilty)..
Tiferet Yisrael - "be careful with the Shema and prayer" - the intent is not just that one recites the shema and prays or that one does not transgress the times. For this a complete obligation (chiyuv gamur) and our sages are speaking only of chasidut (beyond minimum obligation) (as written in Bava Kama 30a). Rather since they are a complete obligation and a man says them several times a day, therefore it is common for one to not have good intent in them. Therefore, the Tanna exhorted here that one should be careful to have intent very much.

"reading the Shema" - because one reviews to himself all the fundamentals (ikarim) of our holy faith. In the first parsha, emunah in the yichud Hash-em, blessed be He, (faith in the absolute Unity of G-d, i.e. that G-d and only G-d is absolutely One as explained in Duties of the Heart, Gate 1), love of Him, fear of Him, and torah study. Namely, one's obligations towards G-d.

The second parsha contains emunah (faith) in the divinity of the torah and guarding the mitzvot, as it opens: "And it will be if you hearken.. which I command". It also contains emunah in providence of reward and punishment in this world and also hints on reward and punishment in the next world, as it ends "in order that you lengthen your days liek the days of heaven and earth". And this is only possible in Olam Haba. That is to say, do My mitzvot only for that, not for this world.

The third parsha exhorts greatly not to be swayed by the enticements of the yetzer hara (evil inclination), by lusts or heretical thoughts, as written: "do not stray after your hearts", namely, the yetzer har, "and after your eyes", namely, bad thoughts (machshavot to'ot). For all sins of this world stem from these two.

Since all the things in these parshas are fundamentals (ikarim) to all Jews and their obligations in this world, the Holy One, blessed be He, commanded us to review them every day. Thus if despite all this, a man says them without intent (kavana), then all his recital (of the Shema) was for nothing.

Likewise for prayer. Besides that in all of them one is speaking to the King, as written "blessed are You..etc.", and how could one be so brazen-faced then as to not have his mouth and heart equal, but even without this, how could he think G-d will accept his prayer if he did not plead before G-d with great humility (hachna'ah yetera). Instead of this, his thoughts fly to all corners of foolishness and vanity. Perhaps even on matters of sin. How could he not be embarrassed to say at the end of his prayer before the Knower of thoughts: "May the words of my mouth and the meditations of my heart be acceptable to You..".

What will he say if G-d answers him angrily: "what did you think in your mind?"

Therefore, our sages said: "a person's prayer is no heard unless he puts his soul in his hand", "his soul" refers to his thoughts, "in his hand" refers to watching over them well so they don't sway and so he does not forget before Whom he is standing, as written: "Let us lift up our hearts to our hands, to God in heaven" (Eicha 3:41).

"as [a plea for] mercy and a supplication before G-d" - to pray in a pleading manner, like a poor man standing broken hearted at the entrance to the king (Berachot 29).

"For gracious and merciful is He, slow to anger, abounding in kindness, and relenting of the evil" - there are three types of prayer and all are included in this verse:
1. that G-d saves him from troubles, and even if he sinned and "when the ox is fallen, sharpen the knife" (Shab.32a), nevertheless, that G-d will hold back anger and not punish him perhaps he will repent.

2. that G-d benefits him with some good despite that he does not deserve it according to his deeds, i.e. that G-d increases His kindness to him.

3. When he repents, that G-d forgives his sins completely and witholds the evil he deserved.

All three types of prayer are accepted only through G-d's being gracious and merciful to you. Namely, when you pray in the way of supplications (tachanunim).
Bartenura - "do not make your prayers fixed" - like a man who has a fixed debt and says: "when will I unload this debt on myself?" Alternatively, "fixed", like a man who is used to reading one chapter or one parsha. He reads it rotely, not in a supplicating manner like one who seeks mercy.
Bartenura - "for gracious and merciful is He" - He wants supplications and through the supplications, He immediately has mercy.
Rashi - "for gracious and merciful is He" - from here [we learn] that He wants tachanunim (supplications) and has mercy immediately.
Rabeinu Yonah - that he prays before G-d like a poor man who pleads to someone asking for something he needs. For "a poor man speaks with supplications" (Mishlei 18:23). And not like a man who asks for something he does not need, whereby he does not plead with a lowly heart and broken soul. Every person needs to ask on his soul. "For there is no righteous man in the land who does good and does not sin" (Kohelet 7:20). Likewise, the prayer should not be on him like a burden and he should not pray like one paying a debt.

"for gracious and merciful is He" - for every person needs mercy. If times are good when G-d witholds wrath from him and graces him, it is not due to his own merits that G-d has mercy on him. Thus, one must plead to Him lest G-d relents on witholding the evil due to a sin (shema yigrom hchet). For a miracle is not done all the time.

"do not be wicked before yourself - to not be wicked in your own eyes, [thinking] one is unable to repent. For then he abandons hope of repenting.. Likewise one should not be a tzadik in his eyes, as our sages said:
"He (the unborn child) takes an oath: 'be righteous, and be never wicked; and even if all the world tells you, you are righteous, consider yourself wicked" (Niddah 30b). i.e. not literally a wicked person but rather let it be in your eyes as if you are half meritorious and half guilty. Thus if one does a mitzvah - fortunate is he for he inclined himself to the side of merit. But if he does a sin, woe to him for he inclined himself to the side of guilt.

This is what our sages said: "a man should always see himself as if he is half meritorious and half guilty, as written (Mishlei 14:16)'the wise man fears and turns from evil'" (Kidushin 40a).

i.e. for the wise man, even though he turns from evil, he fears because he is in his eyes like a wicked man. Thus he runs after mitzvot so they incline him to the side of merit and flees from sins so they don't incline him to the side of guilt.
Ruach Chaim - "before G-d (literally: before the Place)" - the matter is as our sages taught: "the Holy One, blessed be He, is called the Place of the world" (Ber.Rabba 68:9). And as written in the holy Zohar: "human beings should fear before their Master. For He is great and rules [over everything], and [He] is the root of all the worlds" (Zohar chelek 1, 11a). This means He holds and sustains all the worlds, just like a place (space) holds something placed in it. This is the meaning of: "before the Place (G-d)", i.e. one needs to pray with awe and fear and self-sacrifice (mesirut nefesh mamash) to Him for He is the Place of the universe. And like our sages said: "a man's prayer is not listened to unless he puts his soul in his palm" (Taanit 8a).
Bartenura - "do not be wicked before yourself" - do not do something which today or tomorrow you will call yourself wicked due to this. Alternatively, the Rambam explained - do not be wicked in your eyes, i.e. do not consider yourself a wicked person. For due to this, you will go off to evil ways completely..
Tiferet Yisrael - "do not be wicked in your own eyes" - this too greatly prevents intent (kavana) in prayer. Namely, when one considers himself to be wicked and abandons hope of mercy and he thinks all his prayers won't help him.
Sforno - the level of "fear of sin", which Rabban Yochanan ben Zakai praised, will be attained by you through zehirut on the reading of the shema. For it exhorts on the greatness of the holy King who warned against sin. (translator: for the Shema speaks of the absolute Unity of G-d, namely, that He is devoid of any boundary, limit, plurality, etc. and is thus infinite as explained in the first gate of Duties of the Heart).

Through this your prayer will not be fixed (kevah), like one who unloads a burden. But rather [beseeching] for mercy and supplications. For through prayer you will sense that you need to obtain all your requests from Him forever and you will fear sinning before Him.

"And do not be wicked before yourself" - as did Elisha (Acher). For since he thought there was no remedy for him, he did not want to repent. Rather it is proper that if you sin, think that there is a remedy still while G-d is witholding the evil.
Maharal - a man needs to be careful in Shemah and prayer. For these two are "receiving [on oneself] the yoke of Heaven". Likewise, prayer is service (avodah) of G-d and man needs to be careful in this due to his being a man. For he was created for this purpose of serving his Creator. Therefore, in man's being a man, he needs to be careful of the shemah and prayer. For through this, he accepts upon himself the yoke of Heaven and His sevice, as he was created to for..

"And when you pray.." - man's prayer needs to be supplications (tachanunim), like a man who seeks from another in a supplicating manner (derech chanina). But if he prays in a fixed and obligated manner, this is not complete service. For service is when a man [feels he] needs G-d and is totally dependent on Him. This occurs when he thinks that everything G-d does to him is a compassion and a grace (i.e. a free, undeserved gift out of compassion for him).

But if when he prays his mindset is that he deserves that G-d fulfills his request, then he is not completely dependent on G-d. Therefore, the prayer must be in the way of supplication, and seeking from G-d in the way of supplication. And then certainly man needs G-d.

Therefore, if the prayer is like a burden on him, that it seems he just wants to discharge his obligation - this is not considered prayer, which is a service to G-d teaching that man is dependent on G-d.. For when the prayer is in a manner that man is totally dependent on G-d as in truth he is, and his prayer is supplications, G-d will fulfill his request...

And the primary way of supplications is that man lowers himself before G-d, blessed be He, and prays before Him like a slave before his master.

This matter is not in thought alone, only in deed, namely, the prayer itself, i.e. the speech, that he lowers himself before G-d...
Chachma u'Mussar 1:83 - "And when you pray, do not make your prayers fixed but rather as [a plea for] mercy and a supplication..." - for the primary thing in prayer is to implant in a man fear of Heaven, that he understands well that all his life and needs depend on He who spoke and created the world..
Chachma u'Mussar 1:110 - "but rather as [a plea for] mercy and a supplication" - for man does not need to remind G-d what he seeks. For if he will be righteous, the Holy One, blessed be He, will give him without his asking. Rather the primary thing in prayer is to remind oneself that there exists a Creator of the world and all one's life and needs depend on Him. When one contemplates this well, through this he fulfills the mitzvah of fear of Heaven.
Siftei Daat on Avot (R.Yerucham Levovitz) - "And when you pray, do not make your prayers fixed but rather as [a plea for] mercy and a supplication before G-d..." - the Ramban writes (Shemot 13:16): "the intent in the verbal reciting, the synagogues and public prayers is so that people will have a place to assemble and thank the Almighty who created and formed them and so they should declare this before Him saying: 'we are Your creations'" end quote...
Chachma u'Mussar 2:1 - the primary service of G-d stands on faith in divine providence (emunat hahashgacha). But since all matters of the world appear only in the way of cause and effect, thus in order to picture to oneself that it is all from G-d - this is the matter of prayer. Due to this a man need to seek mercy and supplications, etc. mamash (literally) like a poor man asking at the door, in order to bring the picture closer. This is the reason prayer is called "Avodah" (service of G-d), and that which he asks for his needs, this is to remind himself that he is in G-d's hand every second. For he does not at all know what is truly good for him, and he only needs to trust G-d that He will do what is best for him, as king David said: "I calmed and quieted my soul like a suckling on its mother" (Tehilm 131:2).
Kochvei Ohr 9 - the purpose of G-d's will in all this seems to be that it is all for man's good. For in truth, the Holy One, blessd be He, does not need man's prayer. For nothing is concealed from Him. Therefore, it is known that the purpose of man's creation in this world is only in order to benefit him afterwards; to bequeath to him eternal life and eternal delight when he comes for reward in the world of recompense (gemul) - due to the fruit of the labor of his hands and toil in torah and mitzvot. This is explained at length in chapter 1 of the "Path of the Just", see there.

It seems that due to this comes the mitzvah: "guard yourself lest you forget the L-ord your G-d" (Devarim 8:11).

Rabeinu Yonah writes in Shaarei Teshuva (3:27): "through this [verse] we were exhorted to remember G-d, blessed be He, at all times". end quote

i.e. to not forget G-d, blessed be He, for even one second. For when the remembrance of G-d is in his heart always, he will walk in the just ways of G-d always, to guard the whole torah and the mitzvah, as written in the Shulchan Aruch (Orach Chaim 1:1, Rama): " 'I have set Hash-em before me always' (Tehilim 16:8) - this is the general principle of the torah and of the righteous.." see there.

But when the soul is imprisoned in the prison of the physical, and "the inclination of the heart of man is evil from his youth" (Gen.8:21), and his heart turns towards the physical pleasures, then man is liable to forget G-d and sway from the path of the torah and the mitzvah. Thus the divine wisdom saw to set a path for man to remember Him always. Namely, through man's asking for his needs everywhere he turns whether in secular or spiritual matters. For "if G-d did not help him, he would not be able to defeat his inclination which strengthens over him every day and seeks to slay him" (Sukkah 52b).

And G-d commanded man to pray to Him always and seek mercy before Him on his needs. This is the reason why man's eyes should be lifted always towards G-d and that the remembrance of Him be in man's heart always; not forgetting Him for even one second in order that man walk in His ways to guard the whole torah and mitzvah.
Ketav Sofer Hachadash al hatorah, Avot - a man does not know what is good or bad for him. If he seeks wealth, perhaps it will corrupt him or bandits will come at night and kill him and take everything. And the wise man already said: "There is a grievous evil that I saw under the sun; riches kept by their owner for his harm" (Kohelet 5:12).

If he prays for life, perhaps he wil not live well and maybe he will corrupt his ways and it is better for him that he dies meritorious (Sanhedrin 71b, and as we find by Chanoch). Likewise for other things.

Thus, it seems difficult that we pray on life, livelihood, sons, etc., especially on the high holidays: "remember us to life (Zachrenu l'chaim)", "in the book of life". How do we know this is good for us?

Rather, our prayer is on condition. If G-d sees that this is good for us but our deeds caused us to not deserve this good, therefore we make supplications before G-d that He forgive us and annul the evil we deserve and inscribe us in the book of life and parnassah (livelihood) if it is good for us.

But if it is bad for us, we are not asking for it. This is the meaning of "don't make your prayer fixed", i.e. to not pray on something to fix yourself on this that G-d should grant your request. For who knows if it is good for you?

Rather let your prayer be "mercy and supplications to G-d.. for He relents the evil". Namely, if the thing is evil before You, G-d should not give it to you even though you deserve it. And if the thing is good before You, then G-d should relent on the evil and give you this thing even though you deserve evil instead.
Avodat Yisrael, Avot - it seems to me to explain in the way of the Rashba. When one stands in prayer, he needs to be careful in three things.

One, to not think one is worthy of having his request done. Rather, to hope for kindness of G-d, that He should bestow on him a free gift, as written by Moshe Rabeinu: "I pleaded (vaetchanan) to G-d" (Rashi - "the word 'chanun' in all cases is an expression of signifying a free gift").

Two, one needs to know that the Creator can certainly help him and to not doubt this.

Three, to put one's trust only in Him alone and that besides Him there is no other help.

On this the sages enacted the first three blessings of the Amidah. In the first blessing "who bestows acts of kindness" (gomel chasadim tovim), to teach that man does not have (merit) of his good deeds (since G-d helped him).

In the second blessing: "who revives the dead, supports the fallers, heals the sick, and unbinds the bound" (mechayei metim, somech noflim, rofei cholim, matir asurim) - to believe that He is all-capable.

And in the third blessing: "You are holy..and holy ones praise You forever.." Holy ones (kedoshim) refers to the upper worlds. They praise You forever for all admit that besides Him there is no king, redeemer or savior (melech goel u'moshia).

Similarly, in the Shemah is clarified two of these three aspects. "I will give the rain of the land in its time" - that He has the power to do everything. "guard yourselves lest..and He will close the heavens". And when I don't give rain, you will not be able to be saved by anyone else...