The Pardes Yosef, quoting Rabbenu Ya'acov Algazi, writes that Jacob had special intentions in sending real angels to meet his brother Esau.

"Angels" allude to "Peace." Jacob's desire was to make peace with Esau, not to conquer him. The Jerusalem Talmud states that angels are composed of fire and water (Rosh HaShanah chapt. 2). The last verse of the Kadish prayer states, "He who makes peace in the heavens, may he also make peace for us and all Israel." Making peace in the Heavens refers to angels. They are the epitome of peace since their very composition is the peaceful existence of two naturally antagonistic forces, water and fire. By sending angels, Jacob was telling Esau that he wanted to make peace. Since Jacob was the first to be conceived, he was second to be born…

Esau maintained that he was the firstborn. Jacob however knew that he himself was actually the firstborn. Since the Patriarchs were in the "mind" of G‑d when he created the world, they were "created" first. Jacob also knew that he was conceived first, from Isaac's first drop of semen. Since Jacob was the first to be conceived, he was second to be born. Rashi (Gen. 25:26) compares the idea to a very narrow cylinder. Two stones were put in one after the other. The one put in first, will be the second one to come out. The one put in second will come out first. Esau who was conceived second, therefore was born first. Jacob who was born second, was actually conceived first. (See the Lecha Dodi prayer where the same expression is used concerning Shabbat; the last day to be created, but the purpose of all G‑d's creation.) Angels were created before humankind - on the second day; people weren't created until the sixth day. Nevertheless tzadikim are greater than angels, since the angels are subservient to them.

Jacob was hinting to Esau, just as these angels whom I am sending to you, even though they were created first, are nevertheless secondary to man, so does the right of the first born belong to me, even though you were the first to be born. Jacob…managed to keep all the 613 mitzvot even under the most adverse circumstances…

How do we know that the angels that Jacob sent were real angels? One of the most original answers is found in the Pardes Yosef. Jacob instructs his messengers to tell Esau, ". . .I lived with (my uncle) Laban, and I tarried there until now." (Gen. 32:5)

On the word "I lived" (in Hebrew, "garti"), Rashi comments the letters in the word "garti" are the numerical equivalent of 613, the number of mitzvot in the Torah. Jacob is telling Esau, "Although I lived with the wicked Lavan, I still kept all the mitzvot of the Torah."

As is known, when a person does a mitzvah, it creates an angel, an intercessor for him who will testify that the person did engage in mitzvot. Jacob, who managed to keep all the 613 mitzvot even under the most adverse circumstances, certainly created many angels. These were the angels that he dispatched to Esau; real angels.

(First published in B'Ohel Hatzadikim, Vayishlach 5762; www.nishmas.org)