G-d had promised Jacob that He would be with him, and had Jacob believed this and not feared Esau, Esau would have gone on his way. Through his fear, Jacob brought Esau upon himself by sending him messengers and by his servile use of, “Your servant Jacob.” Tanchuma Yashan (Vayishlach,4) teaches, “Jacob sent [vayishlach] messengers...to his brother Esau” (Gen. 32:4): G-d lamented: “Alas [Vai!] Jacob was sending messengers to Esau!” Likewise, regarding the verse, “So shall you say to my Lord Esau” (32:5), our sages comment (Bereshit Rabbah 75:11), “G-d said to him, 'You degraded yourself and called Esau 'my lord' eight times. I swear that I shall make eight of his offspring precede yours as kings.”
To understand the pitfall of lack of bitachon (trust in G-d), we must ponder the following verse: “He selected a 'mincha' for his brother Esau from what he had with him... These he gave to his servants... He said to his servants, “When my brother Esau encounters you, he will ask, 'To whom do you belong?'... You must reply, 'It belongs to your servant Jacob. It is a 'mincha' to my master Esau'”...Jacob said to himself, “I will win him over with the 'mincha' that is being sent ahead”... He sent the mincha ahead. (Gen. 32:4,17-19,21-22) A 'mincha' is a gift or present, but it is also the name of an offering or prayer. The offering whose specific name is mincha is brought from plants, either wheat or barley, and is called mincha because it is brought not only as a gift or present but also out of self-sacrifice and trust in G-d.
Our sages said (Menachot 104b): Why in the case of the mincha does it say "nefesh", (soul)? [“If an individual [nefesh] presents a meal-offering to the L-rd” (Lev. 2:1)], whereas regarding the olah, or burnt-offering, it says, “When one person [adam] brings an offering to the L-rd” (Lev. 1:2).] G-d said, “Who normally brings the mincha? The poor man. I shall treat him as having sacrificed his life before Me.” A poor man is unable to bring an animal, and even the flour he brings for his meal-offering involves self-sacrifice for him. Surely this is the true purpose of the korban, or sacrifice – that one sacrifice oneself and thereby bring oneself closer to G-d. The poor man, although even the meal-offering is as hard for him as sacrificing his life, still brings it, trusting in G-d to worry for him about his livelihood. This offering is called 'mincha', from the word "nach", “passed away”, as if the poor man bringing the mincha has died. For that same reason, the prayer preceding evening is called mincha.[...] It is called this because when the sun is already turning westward to rest [lanuach], to set, this is the time of mincha and of trusting in G-d. The light is dimming, darkness is approaching, and a person trusts that after the darkness of night, the sun will rise again and there will be light. The time for mincha is when sunset and darkness are approaching. This is why it is called mincha. Every mincha is tied to trust in G-d, and to poverty and humility before the One Who is Master of all. G-d will bring light and day once again. He will bring a livelihood to the poor man who brought Him his fine flour. He will save Israel from all its mighty enemies ...
[...] Jacob took the mincha, our gift to G-d, representing man's lowliness before his Maker, and his faith and trust in Him, and he transferred these sentiments to Esau. This reflected great lack of bitachon (trust in G-d), as in Rashbam's explanation of why Jacob was smitten in hist struggle with the angelic prince of Esau (on Gen. 39:29): Jacob was smitten and ended up with a limp, because G-d made a promise to him while he was fleeing. Just so, all who refuse to take G-d's path, or who take an opposing path, are punished.
In Rav Kahane's “Peirush HaMaccabee” we find: There were two people to whom G-d made promises but were afraid…: One was the choicest of the Patriarchs – this is Jacob, as it says, For Hashem chose Jacob to Himself (Psalms 135:4) [i.e. this verse testifies that Jacob was the chosen of the three Fathers]. And G-d said to him, And behold I am with you (Genesis 28:15) – and yet, eventually he was afraid, as it says, And Jacob was greatly afraid (ibid. 32:7). And the other was the choicest of the prophets – this is Moses, as it says, He said He would destroy them [the Israelites], had Moses, His chosen one, not stood in the breach before Him (Psalms 106:23). And G-d said to him, Because I will be with you – and yet, eventually he was afraid [of Og, king of Bashan], as it says, And Hashem said to Moses: Do not be afraid of him (Numbers 21:34); and one would only admonish “do not be afraid” to one who is afraid. – (Genesis Rabbah 76:1). This commandment, do not be afraid, is a difficult one to obey, and a major commandment. But the person whom G-d has sent on His mission must stand firm in his trust in Him. And if he has committed sins, he must understand that even though sins can indeed annul G-d’s promises, this will not happen as long as he is fulfilling a defined mission, according to G-d’s specific decree. [...] There is a moral here. Jacob feared Esau only because he was concerned that his own sins might have caused G-d to annul His promise to him: All these years, [Esau] was dwelling in the Land of Israel – meaning that he is coming against me with the power of having settled the Land of Israel… and meaning that he is coming against me with the power of having honored his father and mother (Genesis Rabbah 76:2). Nevertheless, he was wrong to be afraid, and was punished for having feared Esau. G-d had, after all, given him an explicit command – which entailed precisely the attributes of faith and trust in G-d – to return to the Land of Israel; and He surely would not have commanded him to endanger himself by returning to Israel had his sins been liable to annul the promise. To the contrary: this command was designed to test his trust in G-d against Esau – but he was afraid, and was therefore punished.
Faith and trust in G-d are no small matter. The Jewish People must prove their trust in G-d by difficult, frightening, and sometimes ostensibly dangerous acts, acts that demand of Israel courage, acts which by their very nature show disdain for the non-Jew, anger him and threaten to bring a confrontation between him and Israel, and all must be performed with complete faith and trust that if Israel do what is decreed upon them, then G-d, too, will fulfill what he promised His treasured nation.
Precisely this proves one's true faith and trust, for it is impossible that one who fears mortal man really believes in G-d. Real trust in G-d requires the Jew both to trust in Him and cast off all fear of mortal man and reliance on human aid. [...] Whoever accepts this principle of bitachon (trust in G-d) unreservedly, truly believes that G-d is the One Supreme Power, G-d of heaven and earth. Whoever hesitates, whoever fears the non-Jew, shows that he questions G-d's ability to help His people. It is doubtful, whether he completely believes in G-d as an Omnipotent Supreme Power.
Compiled by Tzipora Liron-Pinner from "The Jewish Idea" and "Peirush HaMaccabee on Shemot" of Rabbi Meir Kahane, HY"D