Sefat Emet, Genesis, Vayishlach 15:6

במדרש על שליחת המלאכים מביא הפסוק מחזיק באזני כלב. דמיך הי’ ועוררהו כו’. נראה דחז”ל למדו מפסוק דכתיב ושכח כו’ אשר עשית לו ושלחתי ולקחתיך והיא שלחה אליו את דבורה נראה דהי’ נשכח אצל עשו השנאה. וי”ל ע”ד הרמז בפסוק כאשר ילדה את יוסף שהוא בחי’ הזכירה ממילא נפל עשו בשכחה. כי כשזה קם זה נופל לכן אמר שלחני כו’ וכ”כ במחיית עמלק זכור אל תשכח שבזה תלוי מחיית זרעו של עשו. ומה ששלח המלאכים לפי פשוטו יתכן לומר כיון שהקב”ה הבטיחו והשיבותיך אל האדמה הזאת הי’ בטוח שישלים עמו עתה בדרך:

In the Midrash on the sending of the angels, it brings the verse, “One who seizes a dog by the ears.” He was asleep, and you awakened him, etc. It seems that the Sages learned this from the verse that says, “and he forgot … what you did to him,” and, “I will send and take you,” and, “she sent for him, for Deborah,” for it seems that the hatred had been forgotten from Esau. And it may be said, by way of allusion, in the verse, “when she gave birth to Joseph,” that Joseph is the aspect of remembrance; automatically, Esau fell into forgetfulness. For when this one rises, the other falls; therefore Jacob said, “Send me,” etc. And likewise regarding the eradication of Amalek: “Remember, do not forget,” for the obliteration of Esau’s seed depends on this. And the reason he sent the angels, according to the simple meaning, may be that since the Holy One, blessed be He, had promised him, “I will return you to this land,” he was confident that Esau would now make peace with him on the way.

The Sefat Emet explains that Jacob’s act of sending messengers to Esau is compared in the Midrash to waking a sleeping dog—potentially dangerous because it reawakens old hostility. Yet, he suggests that Esau’s hatred had actually faded. The birth of Joseph, associated with remembrance, caused Esau to fall into forgetfulness, for spiritual forces rise and fall in opposition. This dynamic also parallels the command to remember and not forget Amalek, whose downfall depends on Israel’s remembrance. Despite these deeper currents, Jacob’s sending of messengers can also be understood simply: God had promised him safe return, so he trusted that reconciliation with Esau was possible.

Summary: The Sefat Emet teaches that Esau’s forgotten hatred was stirred by Jacob’s outreach, yet spiritually Joseph’s quality of remembrance weakened Esau’s force. Jacob acted confidently because of God’s promise of safe return.