Vayishlach

Our parsha continues Yaakov's departure from Lavan and his travels to his parents’ home. He is wary of Eisav's hatred which is still strong, so Yaakov tries to pacify him by sending messengers to tell his brother that he's coming back. The messengers return with the news that Eisav’s on his way to you with an army of four hundred men. Yaakov is afraid and splits his camp in two so that if one is hurt, the other can get away. Then, he sends an enormous gift to Eisav, crosses the river with his family, goes back alone over the river where he is confronted by the angel of Eisav and they battle through the night.

There are many interpretations of this narrative, specifically why Yaakov went back himself. Rashi relates the midrash that says he went back for some small jugs he left there, while others say they were filled with oil and he went back for the oil. The Rashbam gives us a totally different viewpoint by saying that Yaakov crossed back over the river himself to run away. He was so traumatized by the thought of having to deal with Eisav again, that, after he got the rest of his family across the river to safety, he was just going to run away. Then, the angel fought with him all night to stop him from running away  to show him that Hashem's word will be honored and he won't be harmed by Eisav.

How do we understand this? Why would Yaakov run away?

After the Torah tells us that the angel wrestled with Yaakov all night, striking Yaakov in the hip when he couldn't overcome him, leaving Yaakov with a limp. Then, right after his encounter with the angel, the Torah states, he lifted his eyes and Eisav was coming with four hundred men. Reb Zalman Sorotzkin says that we saw that Yaakov prepared himself with three things, to pray that Hashem help him, to appease Eisav with the gift, and to prepare for war. At the last moment, however, Hashem showed him that he could rely neither on wealth or strength. Some wealth brings nothing but harm to its owners, as He showed him by the fact that by going back for the small jugs he put himself in mortal danger. As for physical strength, a man had suddenly come to kill him, causing him to fight all night and leaving him wounded. Dead tired and limping, he was in no condition to fight Eisav. Yaakov saw that the only path open to him was that of prayer. He lifted his eyes to Heaven and said, “I shall not trust in my bow, neither will my wealth save me. Only You shelter me from trouble.” Then Eisav came in peace, hugged him and kissed him, so Yaakov had nothing to fear.

Rabbi YY Jacobson explains that Yaakov was human and had natural fears.  Even though it had been so many years, the thought of seeing his brother, who wanted to kill him, again, frightened him. Unresolved issues don't just go away; even though it was years later, all the trauma was still there. He didn't want to deal with it, so he decided to run away. When Hashem sent the angel to stop him, Yaakov realized that you can't run away from your problems; one must face his fears, pray to Hashem to help, and, with Hashem’s help, he will succeed. The Torah is teaching us that it's normal to fear. Even Yaakov was afraid. However, the Torah is also showing us that, with prayer, we will be able to overcome any obstacle. No matter what our fears, we shouldn’t run away from our problems, but just put our faith in Hashem and He will help us overcome!