At the beginning of Parashat Vayishlach, Yaakov sends messengers to Esav:
“Jacob sent messengers [malakhim] ahead to his brother Esau in the land of Seir, the country of Edom.” (Bereshit 32:4)
There is a debate among the commentaries as to whether these were human messengers or divine ones (angels). Rashi, following the midrash, says they were angels, and Ibn Ezra, Radak and others say they were human messengers.
At first this might seem like a classic disagreement among the sages, similar to whether the Sukkot in the desert were literal clouds or the Clouds of Glory. But if we look a few verses back, at the end of Parashat Vayetze, we will see malakhim once again:
“Jacob went on his way, and angels of God [malakhei Elohim] encountered him. When he saw them, Jacob said, “This is God’s camp.” So he named that place Mahanaim.” (Bereshit 32:2-3)
The nature of these angels is also subject to interpretation and speculation by both ancient and recent commentaries. But one thing is clear – angels play a significant role in the story of Yaakov, and more so than in the lives of his father or grandfather.
He has a vision of angels when he leaves for Haran, an angel guides him in his plan to leave Lavan (Bereshit 31:11), and then he eventually fights with an angel later in Vayishlach. What do all these angelic encounters have in common?
As the debate of the opening verse of Vayishlach indicates, the word malakh simply means “messenger.” While some malakhim are divine angels, others are clearly human messengers. But what they have in common is they are sent to perform a task. This sense of mission – shlichut – is what Yaakov needs constant reminding of.
In the beginning of Vayetze, Yaakov flees the Land of Canaan. God appears to him in a dream and tells him that he will eventually return to the land (Bereshit 28:15) and God will help him. While Yaakov might be naturally afraid to return to face his angry brother, he needs to realize he has a mission. Just like the angels who go up and down, he too will leave the land and return.
In Haran, Yaakov needs another nudge, and so the angel lays out a plan that will ensure his financial security when he leaves Lavan, but reminds him also that he needs to return.
After he finally separates from Lavan, he once again encounters angels. This is when he should courageously face Esav. But instead of going to speak to his brother himself, he takes malakhim, which from the proximity to the previous verses seem to be the same angels, and sends them to Esav in his stead.
This does not go as planned. The angels warn him that Esav is coming at him with a force of 400 men. Will Yaakov realize he himself is on a mission, and follow through?
Unfortunately, no. As Prof. Yoni Grossman proves in his book, in the middle of the night, Yaakov flees (again)- with no intention to return. But an angel encounters him once again, and prevents him from avoiding his mission. During this struggle, Yaakov realizes he has the strength and confidence to face Esav directly, and finally fully returns to the land, as God commanded him.