The name Ya’akov (Jacob, יעקב) sounds like the Hebrew word for “heel (akev, עקב).” That’s the wordplay behind the verse that says, “Afterward his brother came forth with his hand holding on to Esau’s heel, so his name was called Jacob” (Genesis 25:26). From a Messianic perspective, the name also hints back to the warning in Genesis 3:15 where the LORD said that the seed of the serpent will bruise the “heel” of the seed of the woman. The “seed of the woman” can be understood as a prophetic title for the Messiah. The Bible mentions the “heels of Messiah” in the Psalms:
Your enemies have reproached, O LORD, they have reproached the heels of Your Messiah. (Psalm 89:52)
The rabbis understood these references to “the heels of the Messiah” symbolically to indicate the final generation that will see the coming of the Messiah. Rabbinic sources refer to the generation of the final redemption as the “heels of Messiah (Ikveta deMeshicha, עקבתא דמשיחא)," or to translate it another way, “the footsteps of Messiah.” When things seem darkest, we should listen for the footsteps of Messiah.
The Mishnah predicts what it will it be like in the generation of “the footsteps of Messiah.”
With the footsteps of Messiah, impertinence increases and famine increases. The vine gives its fruit and wine is expensive. The government turns to heresy and there is no reproof. The house of assembly will be for prostitutes, and Galilee will be laid waste and the [Golan] made desolate. The border inhabitants will go from town to town, receiving no hospitality, and no one will take pity on them. The wisdom of the scribes will sour, and those who fear sin will be rejected. Truth will be sealed away, children will shame elders, and elders will rise before children, as it says [in Micah 7:6], “For son treats father contemptuously, daughter rises up against her mother, daughter-in-law against her mother-in-law; a man’s enemies are the men of his own household.” The face of the [last] generation will be like the face of a dog. A son will not feel any shame before his father. Upon whom shall we depend? Upon our Father in heaven. (m.Sotah 9:15)
Yeshua predicts a time of calamity before the coming of the Son of Man when "the love of most will grow cold" and "a man's enemies will be the members his household" (Matthew 10:30). This was the case with Jacob and Esau. Jacob’s life, his struggle with Esau, and his many travails allude to the difficult days of trial and tribulation that will come upon the world and upon the people of Israel before the coming of Messiah. Even the meaning of Jacob's name hints toward that interpretation. The prophet Jeremiah spoke of the coming judgment on his people as the time of Jacob’s trouble: “Alas! for that day is great, there is none like it; and it is the time of Jacob's distress, but he will be saved from it” (Jeremiah 30:7). Although the seed of the serpent may bruise the heel of Messiah, the Messiah will crush the serpents head beneath his heel.