Esav and his Henchmen
On his way back to the land of Israel, Yaakov is gripped with fear. Someone is waiting for him and plotting his murder. Years ago, his brother Esav swore that he would kill him, but Yaakov had escaped. Throughout his years in exile, Yaakov had heard nothing from Esav. Now, as Yaakov makes his way back to the land of Israel, Esav – who, it would seem, had been preparing for Yaakov's return and had intelligence-gathering scouts stationed along the border – makes his way to the showdown, accompanied by four hundred mercenaries.
The Land of Israel is apparently the crux of the issue. So long as Yaakov remained exile, Esav was prepared to tolerate the situation; Yaakov's intention to settle in his land is not something Esav was willing to accept. In fact, generations later, this same dynamic repeats itself: When the exile of Yaakov's descendants in Egypt comes to an end and they begin their trek toward the Land of Israel, Esav’s descendants, the Amalekites, attack them in an effort to halt their progress toward the Promised Land.
Rabbi Soloveitchik once commented that anti-Semites have a finely tuned radar for holiness. If you want to know what is holy, simply gauge what anti-Semites find most disturbing; circumcision, ritual slaughter, and Jewish sovereignty in the Land of Israel are all modern-day examples.
So long as Yaakov was far away from the Land of Israel, Esav was calm. Now, with Yaakov’s return, confrontation becomes inevitable, and imminent.
The text of Parashat Vayishlach describes Yakkov's preparations for this confrontation in detail, but it also describes Esav's preparations – and the description should give us pause. At first glance the number of henchmen Esav enlists seems to be a completely random number, devoid of any significance beyond the impressive show of strength it is meant to convey. However, either on a conscious or subconscious level, this number may contain a deeper message.
When God promised the Land of Israel to Avraham, a "price tag" was attached: Four hundred years of slavery would have to be endured as "payment" for the rights to the land. Moreover, when Avraham made the very first acquisition of property rights in the Land of Israel, he paid precisely four hundred silver shekels for the family burial plot in Hebron. In other words, the number four hundred is inextricably connected to the Land of Israel.
By all indications, Esav planned to kill Yaakov and re-stake his own claim to the land, but something happened that set his plan awry. According to one Midrash, as soon as the four hundred mercenaries saw Yaakov face-to-face, they abandoned their mission. Apparently, it wasn’t Yaakov's mere physical strength that put them off; they were, after all, well-trained ruthless warriors. What they feared was Yaakov's holiness. As they approached their target, they saw Yisrael - a man who wrestled with, and vanquished, an angel. These brutes knew how to fight, but they did not know how to defeat an adversary such as this. In the words of the midrash, Esav's hired guns were afraid that Yaakov's fiery countenance would burn them alive.
According to a second midrash, a similar thing had happened years earlier. Noting that the angels Yaakov observed in his vision were ascending and descending the ladder, the midrash points out an anomaly in the text: We would have thought that angels – heavenly beings, after all, would first descend to earth, and then return from whence they came. However, the midrash explains, the angels had already come down to earth to see the face of the holy man of whom they had heard, the man whose likeness was engraved on the very Throne of God. The angels stood over Yaakov as he slept on the ground; they ascended the ladder to look at the Divine Throne, and then descended, once again, to compare the celestial image to the face of Yaakov.
Both angels and thugs immediately discerned the holiness of Yaakov; apparently, Esav saw it as well - and when he did, he abandoned any thought of claiming the holy Land of Israel for himself. He made his peace with his brother because it was obvious to Esav that he was "out of his league," and without further delay took off, just as his four hundred henchmen had done. It was clear to them all that the Holy Land was destined for this holy man and his descendants, the Children of Yaakov/Yisrael.
 Bereishit 15:13.
 Bereishit 23:15.
 Bereishit Rabbah 78:15
בראשית רבה (וילנא) פרשת וישלח פרשה עח
וַיָּשָׁב בַּיּוֹם הַהוּא עֵשָׂו לְדַרְכּוֹ שֵׂעִירָה, וְאַרְבַּע מֵאוֹת אִישׁ שֶׁהָיוּ עִמּוֹ הֵיכָן הֵם, נִשְׁמְטוּ כָּל אֶחָד וְאֶחָד הָלַךְ לְדַרְכּוֹ, אָמְרוּ שֶׁלֹא נִכָּוֶה בְּגַחַלְתּוֹ שֶׁל יַעֲקֹב.
 Bereishit Rabbah 68:12
בראשית רבה (וילנא) פרשת ויצא פרשה סח
רַבִּי חִיָּא וְרַבִּי יַנַּאי, חַד אָמַר עֹלִים וְיֹרְדִים בַּסֻּלָּם, וְחַד אָמַר עֹלִים וְיֹרְדִים בְּיַעֲקֹב. מַאן דְּאָמַר עֹלִים וְיֹרְדִים בַּסֻּלָּם, נִיחָא. וּמַאן דְּאָמַר עֹלִים וְיֹרְדִים בְּיַעֲקֹב, מַעֲלִים וּמוֹרִידִים בּוֹ אָפְזִים בּוֹ קָפְזִים בּוֹ שׂוֹנְטִים בּוֹ, שֶׁנֶּאֱמַר (ישעיה מט, ג): יִשְׂרָאֵל אֲשֶׁר בְּךָ אֶתְפָּאָר, אַתְּ הוּא שֶׁאִיקוֹנִין שֶׁלְּךָ חֲקוּקָה לְמַעְלָה, עֹלִים לְמַעְלָה וְרוֹאִים אִיקוֹנִין שֶׁלּוֹ, וְיֹרְדִים לְמַטָּה וּמוֹצְאִים אוֹתוֹ יָשֵׁן.