Rabbi Milevsky's Thought of the Week: Vayishlach - 5778
In the beginning of Pareshat Vayishlach, Yaakov started the process of returning to the land of Israel. Although he did not have to deal with bureaucratic red tape, he did decide to contact his brother. The Torah notes that he sent messengers to Esav, to assess his brother’s attitude towards him. Unfortunately, they came back with a bad report, as they notified Yaakov that, "He is coming to meet you with four hundred men.” Being that Esav was on his way with an army, Yaakov understood that the situation was not good.
The Torah describes him being “greatly afraid and distressed.” The commentators explain that Yaakov was distressed from the fact that he was afraid. Being that our patriarch Yaakov was promised by Hashem that He will return him home, Yaakov should have remained confident of his situation. However, when the emotion of fear took hold of Yaakov, he sensed a spiritual void that caused him distress.