“Jacob sent messengers (malachim).”
– Genesis 32:4
According to Sforno, Jacob sent messengers, in order to find out Esau’s state of mind concerning him (Sforno, sefaria.org). Jacob had spent twenty years working for his Uncle Laban; now, Jacob was returning to his native land, as stated in Genesis 31:13. He was concerned that Esau may have been still harboring resentment towards him, for having acquired both the birthright and their father’s blessing for the firstborn. When the servants that Jacob sent ahead as messengers returned, they reported that Esau was approaching with four hundred men.
Rather than confront Esau, his brother, in battle, Jacob chose to send gifts to him, as part of a three-fold strategy. He hoped to appease Esau’s anger, by way of sending droves of animals ahead to him, through his servants. He also divided his entourage into two camps, placing his servants first, and then his family, so that if the first camp was attacked, the second could escape. Additionally, he prayed to H’Shem, asking Him for reassurance that he would be delivered from the hands of his brother, Esau.
When Jacob prayed to H’Shem, he said of himself, “I am not worthy of all the mercies, and of all the truth, which Thou hast shown Thy servant” (Genesis 32:11, JPS). According to Rashi, he felt as if his merit was diminished, perhaps, because of some sin that he had committed, so that he could not presume to think that H’Shem would deliver him from the hands of Esau (Shabbat 32a).
Nachmanides comments that he “didn’t rely on his righteousness,” nor presume that G-d would intervene; rather, he took it upon himself, to prepare for a potential conflict” (Ramban, sefaria.org). Because he felt unworthy, he took practical measures on his own, in order to avoid a deadly confrontation with Esau. This also reflects the understanding, that the righteous do not rely on the merit of their own performance of mitzvoth (good deeds).
In like manner, it is best not to feel entitled to H’Shem’s blessings in our lives. Instead, we should learn from Jacob, by prevailng upon H’Shem’s gadol chesed, the greatness of His kindness (Sforno, sefaria.org), while also making an effort on our own to overcome our challenges in life. In this manner, we reflect the Talmudic saying in our lives: “if you make an effort, H’Shem will meet you halfway” (Nedarim 39). As is elsewhere written, “And to him that ordereth his way aright will I show the salvation of G-d” (Psalm 50:23, JPS 1917 Tanach).