Many of the commentators say that Yaakov wanted to placate Esav, and to humble himself before him.  On 32:5, which reads “So shall you say to my lord, to Esav: So says your servant, Yaakov”, Ramban comments:  

“He commanded them to say ‘to my lord, Esav;’ we are his, or sent to him to say ‘So says your servant, Yaakov: I dwelt with Lavan…’ Know that the honor that Yaakov showed his brother in his fear, saying ‘my lord’ and ‘your servant’ were because it was the custom for the younger to give honor and higher status to the elder brother as if he were his father…. Yaakov took his birthright and his blessing…. and now, Yaakov is showing him that it is as if that sale held no meaning for him….” 

This view, that Yaakov was being deferential to his brother, is not shared by the Midrash Tanchuma: 

“‘I have dwelt with Lavan…’ That is to say: ‘Even though I lived with Lavan, who is the father of all deceivers, for the past twenty years, I have oxen and donkeys and great wealth.’ He told him so that Esav would think ‘Yaakov crossed the river with nothing but his staff, and worked with him for twenty years! And Lavan is the father of all deceivers, and nevertheless, Yaakov managed to get rich with him and come back unharmed? How will I ever be able to beat him?’” 

One text sees Yaakov as acting deferentially to Esav out of fear, and the other sees him as flexing his muscles and trying to intimidate Esav.  

When we read the plain text of the Torah, we see every sign that Yaakov is afraid of Esav. He prays profusely for Divine protection. He separates his camp into two, so that if Esav attacks one camp, the other might survive. Ramban’s reading of Yaakov as deferential and humble seems accurate. 

Abravanel, however, asks why Yaakov, who was promised from above that he and his descendants would inherit the land, and that he would come safely home, was so filled with dread that he needed to placate his brother and kowtow to him. The Midrash Tanchuma would seem to satisfy Abravanel. 

The Torah here is pointing most clearly to the two ways of responding to fear of another: acting smaller than the other, or inspiring fear in the other. It seems to be a simple power struggle for Yaakov; a common power play. 

If this is the case, then what role does Yaakov’s prophetic experience play? Yaakov saw a vision of angels descending and ascending a ladder, and wrestled with an angel, and earned a new name. None of this seems to influence Yaakov’s state of mind when he actually meets his brother. 

There are two aspect at play. One is the fact that Yaakov’s adversary is his brother, and people’s habits of interacting with family members can override even the most intense Divine revelation. Another is subtly hinted at in the fact that while Esav, when offered Yaakov’s gift, says that he has “a great deal,” Yaakov responds by saying that he has “everything.” This can either be read as part of the negotiation between the two brothers, or it can be seen as reminiscent of their grandfather Avraham’s state of being in his old age; God had blessed Avraham with everything. Similarly, Yaakov is now blessed with everything. 

Shabbat Shalom!