Two Bitter Weepings: Esau's Tears Refused and Peter's Tears Forgiven
Old Testament: Genesis 27:34, 38
Esau having heard his father's words, roared out with a great cry: and being in a great consternation, said: Bless me also, my father. ... And Esau said to him: Hast thou only one blessing, father? I beseech thee bless me also. And when he wept with a loud cry,
Old Testament, also: Genesis 27:41
Esau therefore always hated Jacob for the blessing wherewith his father had blessed him: and he said in his heart: The days will come of the mourning of my father, and I will kill my brother Jacob.
New Testament: Luke 22:61-62; Hebrews 12:16-17
And the Lord turning looked on Peter. And Peter remembered the word of the Lord, as he had said: Before the cock crow, thou shalt deny me thrice. And Peter going out, wept bitterly. ... Lest there be any fornicator, or profane person, as Esau; who for one mess, sold his first birthright. For know ye that afterwards, when he desired to inherit the benediction, he was rejected; for he found no place of repentance, although with tears he had sought it.
The connection
Esau sold his birthright for a meal, "making little account of having sold his first birthright" (Genesis 25:34). When the blessing went to Jacob, Esau "roared out with a great cry" and "wept with a loud cry" (Genesis 27:34, 38). In the Hebrew and the Septuagint it is a great and exceeding bitter cry. But the tears did not change his heart. In the same chapter "he said in his heart ... I will kill my brother Jacob" (27:41). The Epistle to the Hebrews remembers him as a warning: "he was rejected; for he found no place of repentance, although with tears he had sought it" (Hebrews 12:17). On the night of the Passion St Peter denied his Lord three times. "And the Lord turning looked on Peter ... And Peter going out, wept bitterly" (Luke 22:61-62). Two men weep bitterly, and their tears end in opposite places. Esau's tears went on into hatred. Peter's became repentance, and after the Resurrection the Lord asked him three times, "lovest thou me?" and gave him His sheep to feed (John 21:17). St John Chrysostom sets the two side by side in his homily on these verses of Hebrews: "Why did Esau not obtain pardon? Because he repented not as he ought. Wouldest thou see perfect repentance? Hear of the repentance of Peter after his denial." Esau's tears "were not [tears] of repentance, but rather of pride and wrath." Chrysostom is careful to add that the Apostle "does not then exclude repentance". St Paul gives the difference: "the sorrow that is according to God worketh penance, steadfast unto salvation; but the sorrow of the world worketh death" (2 Corinthians 7:10). The Catechism teaches that it was the look of Jesus, full of mercy, that drew Peter's tears of repentance (CCC 1429). Between the two stand the tears of Christ. The same Epistle says that "in the days of his flesh, with a strong cry and tears", He offered prayers to the Father and "was heard for his reverence" (Hebrews 5:7). The Lord who turned and looked at Peter was going to offer Himself, and His heard tears are why Peter's could be heard.
Moral sense
Tears alone are not repentance. Esau wept for the blessing he had lost; Peter wept for the Lord he had wronged. St Cyril of Alexandria says Peter "wept not because of punishment, but because he denied his beloved Lord, which was more galling than any punishment." St Ambrose adds that "those whom Jesus looks upon weep for their sins." So the soul that has fallen should not look first at what it has lost, but at the One who is looking at it. Sorrow that turns toward Him leads to confession and to peace. Sorrow that turns in on itself leads, like Esau's, to bitterness and more sin. "A contrite and humbled heart, O God, thou wilt not despise" (Psalms 50:19).
Anagogical sense
Esau's tears found no place, but the tears of the penitent are not wasted. "They that sow in tears shall reap in joy" (Psalms 125:5). Peter, who wept in the courtyard, fed the Lord's flock and in the end followed Him to death (John 21:18-19). At the last the weeping of all who have turned to Him will be ended by God Himself: "And God shall wipe away all tears from their eyes: and death shall be no more, nor mourning, nor crying" (Apocalypse 21:4).
The Fathers
St John Chrysostom, Homilies on Hebrews, on Hebrews 12:14-17: "Why did Esau not obtain pardon? Because he repented not as he ought. Wouldest thou see perfect repentance? Hear of the repentance of Peter after his denial." And: "Esau too repented; as I said; or rather, he did not even repent; for his tears were not [tears] of repentance, but rather of pride and wrath." St Cyril of Alexandria, in the Catena on Luke 22: "He wept not because of punishment, but because he denied his beloved Lord, which was more galling than any punishment." St Ambrose, in the Catena on Luke 22: "those whom Jesus looks upon weep for their sins."
Warrant
Patristic. St John Chrysostom, preaching on Hebrews 12:14-17, sets Esau's tears, which were not repentance, against St Peter's bitter weeping, which was, and says that the Apostle does not exclude repentance. The Catena gathers the Fathers on Peter's tears: St Jerome (the Lord's look called forth those bitter tears), St Leo, St Ambrose and St Cyril of Alexandria. One link is the site's own rather than the Fathers': no Father in the site's corpora joins Christ's tears at Hebrews 5:7 to Esau's at Hebrews 12:17, though the Epistle uses the words with tears, meta dakryon, only at those two places. Checked in the languages: the Hebrew of Genesis 27:34 has tse'aqah gedolah umarah ad me'od, a great and exceedingly bitter cry, and the Septuagint phonen megalen kai pikran sphodra; Matthew 26:75 and Luke 22:62 say Peter eklausen pikros, wept bitterly, the same root. The Vulgate of Genesis has irrugiit clamore magno, which the Douay follows as roared out with a great cry, so the bitterness is not in the Douay's Genesis; the Vulgate of the Gospels has flevit amare. The lead was Dunk's, from asking whether weeping runs from Cain, Jacob and Esau to the tears of Christ.
Catechism of the Catholic Church, paragraph 1429.
The verses
Genesis 27:34 · Genesis 27:38 · Genesis 27:41 · Luke 22:61 · Luke 22:62 · Hebrews 12:16 · Hebrews 12:17