HEEL (עָקֵב, H6811; πτέρνα, G4761, heel). The word is twice used in a literal sense of Jacob’s taking hold of Esau’s heel while still in the womb of Rebekah (Gen 25:26; Hos 12:3), and four times in a fig. sense.
In the Protevangelium (Gen 3:15), God said that the seed of the woman would bruise the serpent’s head, but the serpent would bruise his heel. This clearly refers to the conflict between Satan and the Son of God and the utter defeat Christ would administer to the foe responsible for His crucifixion at Calvary.
The dying patriarch Jacob in blessing Dan wished that those who wickedly opposed him may find him as deadly an opponent as a serpent. The enemy of Dan is spoken of as a horseman whose horse’s heel is bitten by a poisonous serpent so that the frightened animal rears and throws his rider (Gen 49:17). So may Dan successfully overthrow all his enemies.
Job’s friend Bildad the Shuhite insinuated that Job was like the wicked who bring about their own destruction. A trap seizes him by the heel and he is caught (Job 18:9).
The psalmist laments that the bosom friend whom he trusted and who dined at his table lifted his heel against him—prob. spurned him with brutal violence or perhaps kicked him when he was down (Ps 41:9). Jesus referred to this statement at the Last Passover and applied it to Himself. The bosom friend who ate with Him and then betrayed Him was Judas (John 13:18).
International Standard Bible Encyclopedia (1915)
"The iniquity of my heels" (Ps 49:5 the King James Version) is a literal translation, and might be understood to indicate the Psalmist’s "false steps," errors or sins, but that meaning is very doubtful here. the Revised Version (British and American) gives "iniquity at my heels." the Revised Version margin gives a still better sense, "When the iniquity of them that would supplant me compasseth me about, even of them that trust in .... riches"--treacherous enemies ever on the watch to trip up a man’s heels (compare Ho 12:3). Of Judah it was said, "Thy heels (shall) suffer violence" (Jer 13:22) through being "made bare" (the King James Version), and thus subject to the roughness of the road as she was led captive.
(1) Of the partial victory of the evil power over humanity, "Thou shalt bruise (m "lie in wait for") his heel" (Ge 3:15), through constant, insidious suggestion of the satisfaction of the lower desires. Or if we regard this statement as a part of the Protevangelium, the earliest proclamation of Christ’s final, and complete victory over sin, the destruction of "the serpent" ("He shall bruise thy head"), then the reference is evidently to Christ’s sufferings and death, even to all that He endured in His human nature.
(2) Of the stealthy tactics of the tribe of Da in war, "An adder in the path, that biteth the horse’s heels" (Ge 49:17), by which it triumphed over foes of superior strength.
(3) Of violence and brutality, "Who .... hath lifted up his heel against me" (Ps 41:9; Joh 13:18), i.e. lifted up his foot to trample upon me (compare Jos 10:24).