This week’s Parsha begins with the preparation of Ya’akov Avinu for his encounter with his brother Eisav. Rashi comments that Ya’akov’s preparations included three elements: a gift (option of peace), war and prayer.
In his Tefila which covers four verses, he says:
וַיֹּאמֶר יַעֲקֹב אֱלֹקֵי אָבִי אַבְרָהָם וֵאלֹקֵי אָבִי יִצְחָק יְקֹוָק הָאֹמֵר אֵלַי שׁוּב לְאַרְצְךָ וּלְמוֹלַדְתְּךָ וְאֵיטִיבָה עִמָּךְ:
קָטֹנְתִּי מִכֹּל הַחֲסָדִים וּמִכָּל הָאֱמֶת אֲשֶׁר עָשִׂיתָ אֶת עַבְדֶּךָ כִּי בְמַקְלִי עָבַרְתִּי אֶת הַיַּרְדֵּן הַזֶּה וְעַתָּה הָיִיתִי לִשְׁנֵי מַחֲנוֹת:
הַצִּילֵנִי נָא מִיַּד אָחִי מִיַּד עֵשָׂו כִּי יָרֵא אָנֹכִי אֹתוֹ פֶּן יָבוֹא וְהִכַּנִי אֵם עַל בָּנִים:
וְאַתָּה אָמַרְתָּ הֵיטֵב אֵיטִיב עִמָּךְ וְשַׂמְתִּי אֶת זַרְעֲךָ כְּחוֹל הַיָּם אֲשֶׁר לֹא יִסָּפֵר מֵרֹב:
“And Ya’akov said, “G-d of my father Avraham and G-d of my father Yitzchak, the Lord, Who said to me, ‘Return to your land and to your birthplace, and I will do good to you.’
I am small of all the kindnesses and from all the truth that You have done to Your servant, for with my staff I crossed this Jordan, and now I have become two camps.
Now deliver me from the hand of my brother, from the hand of Eisav, for I am afraid of him, lest he come and strike me, [and strike] a mother with children.
And You said, ‘I will surely do good with you, and I will make your seed [as numerous] as the sand of the sea, which cannot be counted because of multitude.'””
In the second verse, Ya’akov, in his humility, expresses his unworthiness of all the kindness that Hashem has done for him, and apparently is not demanding on his merit that Hashem answer his prayer, rather out of pure compassion and mercy.
Rashi however has a different understanding of this verse;
“My merits have been diminished as a consequence of all the kindness which You have already shown me. Therefore I am afraid, perhaps since the promises were made I have sinned, and therefore I will be defeated by Eisav. “
In other words, according to Rashi the phrase “katonti mikol hachasadim” does not mean that Ya’akov is unworthy of all the chesed that Hashem has done to him till now, or that he is smaller than the kindness shown to him – in that sense the word “mikol” would mean “than all”, but rather it means that Ya’akov has become diminished because of those kindnesses – “mikol” meaning as a result of all – since those kindnesses expended many of his merits, now leaving him with not enough merits to merit more chesed of Hashem to overcome Eisav.
The Ramban takes issue with Rashi and claims that Rashi’s interpretation doesn’t make sense with the continuation of Ya’akov’s prayer. If Ya’akov felt unsure since he no longer had merits, why does he then invoke Hashem’s promise to the Avot in the fourth verse, after already expressing his unworthiness of being a vessel to their fulfillment? The Ramban therefore rejects Rashi’s understanding and explains as mentioned above that it is a statement of humility by Ya’akov before beseeching Hashem to save him from Eisav.
Besides the Ramban’s question on Rashi, how are we meant to understand the idea that one’s merits are depleted as a result of the chesed Hashem does? Are a person’s good deeds equivalent to a currency with which we can barter for chessed from Hashem? If Ya’akov was lacking the” currency” couldn’t Hashem give him credit and save him from Eisav anyway? Ya’akov could have paid back afterwards; after all, we are dealing with the survival of Bnei Yisrael.
Rav Kook explains this concept as follows:
“The human being grows in stature proportionately to his positive actions that he performs and if he receives goodness without any action on his behalf, it is diminishing to his stature. The reason for this is: since miracles and nature both come from Hashem, if one receives goodness through a miracle it is because that person is unable to achieve the result through their own action, therefore it is indicative of their own lacking.
Nature is the act of G-d with man himself, because everything that man does is also the act of God, and there is no difference between whether the means to the end are the forces of reality (including miracles) or man’s agility, intellect and desire. For when he uses them, he is also part of reality which is all the acts of G-d, “all of our actions, you Hashem have done for us.”
The difference though is, that when one actively does these good things, one develops their own individual character, however if one receives the good without action, it diminishes one’s character, as one lives a life of passive reception instead of active giving and creating.
One should cherish a life of creativity and giving, which is a life of activity, which is the preeminent desire of Hashem who wants the utmost wholeness and perfection for his creations.”
According to this, Ya’akov Avinu was saying to Hashem in these words that because of all the kindness that he had received over all those years, chesed which he had not proportionately earned through his own efforts, he has in effect become a lesser, weaker person. What makes a person strong, what builds one’s personality is one’s active effort to do and create goodness. If that good befell a person without the effort it is not only indicative of a lacking in them, but it also has a negative effect on them.
That is why Ya’akov believed that he was not strong enough to overcome Eisav.
We all know that Hashem answered Ya’akov’s prayer and saved him from the hands of Eisav, but was this another chesed? Wouldn’t that be increasing the problem? Apparently the answer to Ya’akov’s prayer was the encounter with the angel/man that wrestled with him all night. Only after this big struggle and effort was Ya’akov able to confront and triumph over Eisav.
 Breishit 32;10-13.
 Rashi Breishit 32;11.
 Rav Kook, Eiyn Ayah Shabbat 2;195.
“האדם הוא מתגדל לפי ערך רוב פעולותיו לטובה, וכל מהי שהוא בהם משולל מפעולה אם מגיעה לו טובה על זה האופן הוא מתקטן, כי הנס והטבע שניהם מעשי ד’ המה. אמנם הנס יבא בהכרח כשאין האדם יכול להיות פועל, א”כ זהו אות כבר על קטנותו. והטבע הוא מעשה ד’ עם האדם עצמו, כי כל מה שהאדם עושה הלא הוא ג”כ מעשה ד’, ואין הפרש בין אם יהיו האמצעיים כחות המציאות או זריזות האדם, שכלו וחפצו, כשהוא ג”כ משתמש בהם, הוא ג”כ חלק מהמציאות שהיא כולה מעשי ד’, “גם כל מעשינו פעלת לנו” . אלא שבהיותו פועל הוא מתגדל ג”כ מצד פרטיותו, ובהיותו נפעל הוא מתקטן, חי חיים של קבלה, לא של השפעה. וראוי לאדם לאהוב חיי השפעה, שהם חיי פעולה, שהוא חפץ ד’ היותר עליון, הרוצה בשלמות היותר עליונה של בריותיו. ולשם זאת התכלית העליונה לא חיסר כל דבר וענין המביא לידי הכשר תכלית זו, שצריך לפעמים ג”כ מדת ההקטנה, כמו שהגידול צריך הוא ג”כ לקטנות. אבל המטרה היא שתבא ממנה ועל ידה הגדלות, ע”כ אמר קטנתי מכל החסדים ומכל האמת אשר עשית את עבדך. אמנם באה לו אח”כ הגדלות ע”י חיים של פעולה, “כי שרית עם אלהים ועם אנשים ותוכל” .”
 Rav Kook, Eiyn Ayah ibid.