Derasha for Parshas VaYishlach
Yaakov prepares himself for his encounter with Esav in three ways - through gifts, davening, and battle.
We normally tend to associate these preparations for his encounter with Esav as a means of either avoiding battle through "natural means" - offering a gift, appealing to Hashem to be saved from defeat in battle at the hands of Esav, and, if necessary, putting up a good fight.
However, this is only half the story.
The Passuk says later on: "Save me from the hand of my brother, from the hand of Esav.
The Or HaChaim, and others, explain this Passuk, that Yaakov is worried about two possible scenarios that may unfold in his meeting with Esav. He is of course worried about coming to physical harm, but even ahead of that he is worried about "his brother" - the fraternal bond of Esav being renewed, and the possibility of being forced to deal with an amicable brother, who wants to associate with Yaakov and his family.
Yaakov knows that it is an inevitable part of his and his descendants' destiny to be intertwined with Esav's - he wrestles with the Sar Shel Esav through the night. Wrestling - arms intertwined with arms, legs with legs, headlocks, one wrestler atop the other, trying to pin each other to the ground - rendering the opponent immobile. And he knows, just as inevitably, that he will be wounded, injured, limping, from this association.
This is true whether the association is confrontational - where the Jews will suffer losses, or fraternal - the Jews will suffer as well.
One Rosh Yeshiva showed me a Medrash:
"And he was limping on his thigh - R' Yehoshua ben Levi was coming from Rome, and when he reached Acre, R' Chanina came to greet him. He found that he was limping on his thigh. He said: You are like your ancestor, 'And he was limping on his thigh'"
What is the meaning of this Medrash? And, since Rabbi Chanina was R' Yehoshua ben Levi's Rebbe, why was he coming to greet his Talmid?
R' Yehoshua ben Levi has just returned from Rome. What did he do there? He hobnobbed with the great Emperor, the Roman aristocracy, to accomplish some political benefit on behalf of the Jews. R' Chanina tells him - it is clear to me that you were somehow affected by your visit to Rome - it is not possible to remain unaffected! As your Rebbe, it is my job to sensitize you to this, and to help you discover where exactly your spiritual level declined.
Yaakov prepares himself for his meeting with Esav "his brother" with these three things as well - he must daven not to be adversely affected, he must be prepared to fight to maintain his standards, and he must offer gifts to his brother, so that when Esav offers to have some of his men travel along with Yaakov, Yaakov has some leverage to be able to hold his brother at arm's length and keep him from getting too close.
In America, we are far more worried about Esav "our brother" than of Esav "the Esav". We have lost millions to assimilation, and it is unavoidable that all of us get affected in some way or another by Esav. We have to daven that we are not overly influenced by Esav's friendly demeanor, and be prepared to put our foot down when too much influence threatens to creep into our homes - our personal Battei Mikdash.
The "gift" to Esav is a very tricky proposition. We recognize that living and interacting in American society requires some concession to Western culture, we adopt some mannerisms and contend with value systems. We spend some of the dollars allocated to us by Hashem on some elements that Esav has to offer - eating out, miniature golf, maybe even other entertainment venues. A person has to walk a very fine line, and consult with Rabbeim, to determine where the line is drawn. We sometimes feel that our children, and maybe ourselves as well, would be miserable if we would completely deny them, or us, all things America has to offer. But it is critical to be vigilant and recognize that this is just to keep the insidious elements of the Esav culture at arm's length - to help us feel content, not to help us indulge.
And that balance is so delicate, that we realize that only through heartfelt supplication to Hashem do we have any chance of crossing the rickety bridge of life over the rushing torrent of Esav-like influences.