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Matthew 26:39

“Jesus Prays in Gethsemane”Matthew 26:36–46

King James Version
And he went a little further, and fell on his face, and prayed, saying, O my Father, if it be possible, let this cup pass from me: nevertheless not as I will, but as thou wilt.

Bible text: King James Version (1769 Blayney text) · Public domain

KJV (with Strong's)
And G2532 he went G4281 a little G3397 further G4281, and fell G4098 on G1909 his G846 face G4383, and G2532 prayed G4336, saying G3004, O my G3450 Father G3962, if G1487 it be G2076 possible G1415, let G3928 this G5124 cup G4221 pass G3928 from G575 me G1700: nevertheless G4133 not G3756 as G5613 I G1473 will G2309, but G235 as G5613 thou G4771 wilt.

Bible text: King James Version with Strong's numbers · Public domain

Berean Standard Bible
Going a little farther, He fell facedown and prayed, “My Father, if it is possible, let this cup pass from Me. Yet not as I will, but as You will.”

Bible text: Berean Standard Bible · Public domain

American Standard Version
And he went forward a little, and fell on his face, and prayed, saying, My Father, if it be possible, let this cup pass away from me: nevertheless, not as I will, but as thou wilt.

Bible text: American Standard Version (1901) · Public domain

World English Bible Messianic
He went forward a little, fell on his face, and prayed, saying, “My Father, if it is possible, let this cup pass away from me; nevertheless, not what I desire, but what you desire.”

Bible text: World English Bible, Messianic edition · Public domain

Geneva Bible (1599)
So hee went a litle further, and fell on his face, and praied, saying, O my Father, if it be possible, let this cup passe from me: neuerthelesse, not as I will, but as thou wilt.

Bible text: Geneva Bible (1599) · Public domain

Young's Literal Translation
And having gone forward a little, he fell on his face, praying, and saying, `My Father, if it be possible, let this cup pass from me; nevertheless, not as I will, but as Thou.'

Bible text: Young's Literal Translation · Public domain

King James Version — Interlinear
29 Greek words
  1. ΚαὶKaiAndG2532CONJConjunction
  2. προελθὼνproelthōnhaving gone forwardG4281V-2AAP-NSMVerb 2nd Aorist Active Participle Nominative Singular Masculine
  3. μικρὸνmikrona littleG3398A-ASNAdjective Accusative Singular Neuter
  4. ἔπεσενepesenHe fellG4098V-2AAI-3SVerb 2nd Aorist Active Indicative 3rd Singular
  5. ἐπὶepiuponG1909PREPPreposition
  6. πρόσωπονprosōponfaceG4383N-ASNNoun Accusative Singular Neuter
  7. αὐτοῦautouof HimG846P-GSMPersonal pronoun Genitive Singular Masculine
  8. προσευχόμενοςproseuchomenosprayingG4336V-PNP-NSMVerb Present Middle Or Passive Deponent Participle Nominative Singular Masculine
  9. καὶkaiandG2532CONJConjunction
  10. λέγων·legōnsayingG3004V-PAP-NSMVerb Present Active Participle Nominative Singular Masculine
  11. πάτερpaterFatherG3962N-VSM-TNoun Vocative Singular Masculine Person Gentilic
  12. μουmouof MineG3165P-1GSPersonal pronoun Genitive 1st Singular
  13. εἰeiifG1487CONDConjunction
  14. δυνατόνdunatonpossibleG1415A-NSNAdjective Nominative Singular Neuter
  15. ἐστινestinit isG1510V-PAI-3SVerb Present Active Indicative 3rd Singular
  16. παρελθάτωparelthatōshould passG3928V-2AAM-3SVerb 2nd Aorist Active Imperative 3rd Singular
  17. ἀπ᾽ap᾽fromG575PREPPreposition
  18. ἐμοῦemouMeG1473S-1SGSNPossessive pronoun Genitive 1st Person Singular Neuter
  19. τὸto[the]G3588T-NSNDefinite article Nominative Singular Neuter
  20. ποτήριονpotērioncupG4221N-NSNNoun Nominative Singular Neuter
  21. τοῦτο·toutothisG3778D-NSNDemonstrative pronoun Nominative Singular Neuter
  22. πλὴνplēnNeverthelessG4133CONJConjunction
  23. οὐχouchnot [it is]G3756PRT-NNegative Particle Negative
  24. ὡςhōsasG5613PRTParticle or Disjunctive
  25. ἐγὼegōI myselfG1473P-1NSPersonal pronoun Nominative 1st Singular
  26. θέλωthelōwishG2309V-PAI-1SVerb Present Active Indicative 1st Singular
  27. ἀλλ᾽all᾽butG235CONJConjunction
  28. ὡςhōsasG5613PRTParticle or Disjunctive
  29. σύsuYouG4771P-2NSPersonal pronoun Nominative 2nd Singular
English is a literal word-by-word gloss of the Greek, not the KJV's wording. Why?

This is the original text the KJV's translators worked from — each Greek word with its own literal English meaning in this verse, prepared by scholars at Tyndale House, Cambridge. The KJV translates whole sentences, not word by word, so its wording differs: one Greek word can become several English words, and the KJV may choose “charity” where the gloss reads “love”. Both are faithful — they answer different questions. For the KJV's own rendering, switch to the KJV text.

Words in [ ] are added by the English.

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Matthew 26:36-45
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This verse

Fallen on his face, Jesus asks his Father whether the cup of suffering and judgment can pass from him, and puts the Father’s will above his own.

“And he went a little further, and fell on his face, and prayed, saying,”

He goes on alone. Face to the ground is the posture of humility and urgent pleading.

“O my Father, if it be possible, let this cup pass from me:”

“My Father” is the address of a Son who trusts. Dynatós, possible, asks whether there is another way, and the cup (potḗrion) is the portion of suffering and judgment before him.

“nevertheless not as I will, but as thou wilt.”

Plḗn turns the prayer from request to surrender. Thélō is to will or desire, and the Father’s willing is set above his own.

Passage studyMatthew 26:36–46

Not As I Will, but As Thou Wilt

Summary

Late at night, after the supper, Jesus brings his disciples to Gethsemane and goes apart to pray. Sorrow presses on him to the point of death, and three times he asks his Father whether the cup can pass from him, each time giving himself to the Father’s will. The three friends he asked to watch with him fall asleep each time. When the praying is done he wakes them and goes forward to meet his betrayer. Here we see how truly human our Saviour is, how much our salvation cost him, and how freely he obeyed.

Jesus comes to Gethsemane

The evening began with the Lord’s Supper, where Jesus gave the cup as the new testament in his blood (Luke 22:20). They sang a hymn, likely one of the Hallel psalms (Psalms 113 to 118) that were sung at Passover, and as they left Jesus told the disciples that they would all be scattered and that Peter would deny him three times (Matthew 26:26–35). From that shared table and those warnings he now goes to a lonely struggle in prayer, and from there to his arrest.

Gethsemane (Gethsēmanē) was a garden or olive grove at the foot of the Mount of Olives (Matthew 24:3), across the Kidron valley from Jerusalem. Jesus and his disciples went there often (Luke 22:39, John 18:1–2), and Mark tells of the same arrival (Mark 14:32). It was Passover, the city was full of pilgrims, and the garden offered quiet at that late hour.

The name comes from Aramaic and means “oil press”. In such a place olives were crushed under great weight to give their oil. Here the Lord began to be pressed by the weight of our sin and of the suffering ahead, before he poured out his life for our salvation.

Jesus tells the larger group, “Sit ye here, while I go and pray yonder.” The word for pray, proseúchomai, means to pray to God, to supplicate and worship, and Matthew uses the same verb again in verses 41 and 44. On the hardest night of his life the Son of God goes to his Father in prayer. He goes further in with three disciples, and then further still alone, and each step shows that the burden ahead is one that he alone can carry.

Why did Jesus take Peter, James and John?

These three were the disciples closest to him. The verb paralambánō means to take along, and Jesus had taken the same three to see the Transfiguration (Matthew 17:1) and the raising of Jairus’ daughter (Mark 5:37). Having seen his glory and his power over death, they are now brought near to his sorrow. As a true man he wanted his friends close beside him in his distress.

How deep was Jesus’ sorrow?

Matthew gives three strong words for it. In verse 37 Jesus “began to be sorrowful and very heavy”. Lypéō means to distress, or to be sad, and adēmonéō means to be in distress of mind, the state of someone troubled and overwhelmed. Then Jesus says it himself: “My soul is exceeding sorrowful, even unto death.” The word in his own mouth is a stronger one, perílypos, grieved all around, intensely sad, a sorrow that surrounds the whole person. “My soul” (psychḗ) is his inmost self, his mind, feeling and will together. “Unto death” (thánatos, death) gives the measure of it, a grief heavy enough to bring him to the edge of dying. Mark records the same words (Mark 14:34), and Luke tells of his agony and of sweat like great drops of blood (Luke 22:44).

The Old Testament knows this language. Job and David speak of a distress that feels like death, and the psalmist speaks to his own soul and asks why it is cast down (Psalm 42:5). Isaiah foretold a Servant who would be “a man of sorrows, and acquainted with grief”, who would carry our sorrows, be wounded for our transgressions, and be led as a lamb to the slaughter (Isaiah 53:3–7). In the garden that Servant has come.

The cause of the sorrow is the cup he names in verse 39, the bearing of the world’s sin and of God’s judgment on it. The sorrow itself is real. Jesus is fully God and fully man, and as man he felt grief and dread and sought his Father’s strength. That is why Hebrews can say that we have a high priest who is touched with the feeling of our infirmities, who was tempted in every point as we are, yet without sin, and who helps us from the throne of grace (Hebrews 4:15–16).

Why did Jesus ask the three to watch with him?

Jesus asked as a man in deep distress asks for his friends. “Tarry ye here” (ménō hōde, remain here) keeps them near, and “watch” is grēgoreúō, to keep awake, to be vigilant. He wanted them awake, alert and praying alongside him. The watching was also for their own sake, to make them ready for the trial about to fall on them, as verse 41 shows. The bearing of sin remained his alone.

“If it be possible, let this cup pass from me”

Jesus “went a little further, and fell on his face, and prayed”. Falling on the face was a posture of deep humility and urgent pleading in Jewish prayer. He begins “O my Father”, and the closeness and trust in that address hold through everything he asks.

What is the cup?

The cup (potḗrion, a drinking vessel) is a picture of a person’s lot or portion, and in the Old Testament it is very often the portion of God’s judgment. Isaiah speaks of Jerusalem drinking the cup of the LORD’s fury (Isaiah 51:17), a psalm speaks of a cup in the LORD’s hand that the wicked must drink (Psalm 75:8), and Jeremiah speaks of the cup of God’s wrath (Jeremiah 25:15).

So the cup before Jesus holds the physical agony of crucifixion and, above all, the judgment of God against human sin. The sinless Son was to be made sin for us (2 Corinthians 5:21), to bear our sins in his own body (1 Peter 2:24), and to undergo the Father’s wrath and separation from him. Because he drank that cup, it is taken out of our hands. Believers receive in its place “the cup of blessing” (1 Corinthians 10:16) and “the cup of salvation” (Psalm 116:13).

Did Jesus want to turn back from the cross?

Jesus held to his mission through the whole prayer. What the request shows is the honest dread of a true human nature before such suffering. “If it be possible” uses dynatós, a word meaning able or strong, and here possible. Jesus knows that his Father is able to do all things, and he asks whether redemption can be accomplished some other way. The asking is sincere, and his obedience is already in it, for the same sentence ends “nevertheless not as I will, but as thou wilt.” The prayer carries no doubt of the Father’s plan and no failure of will.

What does “not as I will, but as thou wilt” mean?

Jesus places what he would choose as a man under what his Father has purposed. Plḗn, “nevertheless”, marks the contrast, and the verb thélō means to will, wish or desire. He has a true human will that shrinks from agony, and he yields it to the Father. Long before this night he had said that he came down from heaven to do the will of him that sent him (John 6:38).

In the second prayer the yielding goes a step further: “O my Father, if this cup may not pass away from me, except I drink it, thy will be done.” The first prayer asked whether the cup could pass. The second accepts that it may have to be drunk. Thélēma is the noun for will, a purpose or decree, here the Father’s plan to save, and “be done” is gínomai, to become or come to pass. This is the petition Jesus had taught his disciples to pray (Matthew 6:10), and now he prays it himself at the greatest cost. Luke records the prayer in the same spirit (Luke 22:42).

Scripture sets this obedience against Adam’s. In a garden the first man chose his own way, and Paul writes that as by one man’s disobedience many were made sinners, so by the obedience of one many are made righteous (Romans 5:19). Paul also says that Christ “became obedient unto death, even the death of the cross” (Philippians 2:8). Hebrews tells us that in the days of his flesh he offered up prayers with strong crying and tears, that he learned obedience by the things he suffered, and that he became the author of eternal salvation to all who obey him (Hebrews 5:7–9). Isaiah had said that “it pleased the LORD to bruise him” (Isaiah 53:10). The cross was the Father’s will and the Son’s free choice together.

Why did Jesus pray the same words three times?

The repetition shows how earnest the prayer was and how long the struggle lasted. “Again” (pálin) and “the third time” (trítos) are plain words of counting, and “the same words” uses lógos, something said, including the thought in it. His heart had one concern, and he brought it back to the Father until the praying was finished. Each time the request came with the same surrender, so the three prayers are three acts of trust, and they are a pattern for us of persevering in prayer under trial. Earnest and repeated pleading was a familiar part of Jewish prayer in distress.

The sleeping disciples

Each time Jesus returns he finds the three asleep. Katheúdō means to lie down to rest, to fall asleep, and Matthew uses it in verses 40, 43 and 45. He also gives the reason: “for their eyes were heavy.” The verb is baréō, to weigh down, in the form bebarymenoi, so their eyes were weighed down. The KJV has “heavy” here and “very heavy” for Jesus in verse 37, though the Greek words differ. His heaviness was anguish of mind, and theirs was weariness. It was late, after the Passover meal and an evening full of hard words, and Luke adds that they slept for sorrow (Luke 22:45–46). Their love for Jesus was real, and their bodies gave way. Mark tells the same story (Mark 14:37–38).

Their sleep leaves Jesus alone. The prophet’s words fit him: “I have trodden the winepress alone” (Isaiah 63:3). His solitude in the garden looks ahead to the cross, where he bore the sins of the world by himself.

Why does Jesus speak to Peter?

Peter was the leading voice among the disciples, and a little earlier he had declared his unfailing loyalty and his readiness to die with Jesus. The question goes to him, though the “ye” takes in all three: “What, could ye not watch with me one hour?” The verb ischýō means to be strong or able, so Jesus is asking whether they had the strength for it. The opening word (hoútō), which the KJV gives as “What”, carries his surprise and disappointment, and “one hour” shows how little he had asked. The rebuke is gentle. It shows his loneliness, and it warns Peter that good intentions need God’s strength. Within hours Peter would deny him (Matthew 26:69–75).

What temptation does Jesus mean?

Peirasmós means a putting to the proof, a test or trial, and it covers both enticement to sin and adversity. The nearest meaning is the trial about to break on the disciples: the arrest, the fear, the scattering Jesus had foretold, and Peter’s denial. More widely it is any trial or enticement that could bring a believer to sin or to fall away. To “enter into” temptation (eisérchomai, to go into, with hína mḗ, “that ... not”) is to go into the trial and be overcome by it. So Jesus tells them to pray for strength to stand in the test, as he had taught them to pray “lead us not into temptation” (Matthew 6:13).

Watching and praying belong together. To watch is to stay awake and alert to danger, and to pray is to ask God for the strength we lack. Jesus had taught watchfulness before, in the parable of the servant waiting for his lord (Matthew 24:42–51) and the parable of the ten virgins (Matthew 25:1–13). The apostles repeat it. Peter, who slept in the garden, later writes “Be sober, be vigilant” (1 Peter 5:8). Paul tells us to pray always and to watch (Ephesians 6:18), and he promises that God is faithful and with every temptation makes a way of escape (1 Corinthians 10:13).

What are the willing spirit and the weak flesh?

The spirit is the inner person that turns toward God, and the flesh is our human nature in its frailty. Pneûma, spirit, is described as próthymos, eager and ready. Sárx, flesh, is the body and, by extension, human nature with its frailties and passions, and asthenḗs means strengthless. The little word dé, “but”, sets the two side by side. Jesus speaks with understanding, since he grants that his disciples mean well. He also warns them that a willing spirit needs God’s help to carry weak flesh through a trial.

Paul describes the same conflict in himself (Romans 7:18–25). He says that flesh and Spirit are contrary to each other and that those who walk in the Spirit do not fulfil the lust of the flesh (Galatians 5:16–17), and that the Spirit helps our infirmities (Romans 8:26). Jesus himself is the one in whom the willing spirit fully prevailed. Awake and praying, he met the temptation to turn from the cross and overcame it.

The hour is at hand

Why does Jesus say “Sleep on now, and take your rest”?

Jesus is telling the three that the time for watching with him is over. The words are best heard as sorrowful irony or resignation, and they can also be heard as a question. On either hearing the vigil he asked for has ended, and his next words call them to their feet. He has kept the watch alone, and he will go on alone.

What is “the hour”?

The hour (hōra) is the time appointed by God for Jesus’ suffering, death and glory, a theme that runs through the Gospels and especially John. Jesus had said that the hour had come for the Son of man to be glorified, and he embraced that hour as the purpose of his coming (John 12:23–28). At the supper he knew that his hour was come (John 13:1–3), and at his arrest he calls it the hour of the power of darkness (Luke 22:53). “Is at hand” is engízō, to draw near. Matthew uses the same verb in verse 46 for the betrayer, so the hour and the man arrive together. The disciples could keep awake for one hour at most, and Jesus now walks into the hour for which he came.

“Behold” (idoú, “see!”) calls for their full attention. The arrest is God’s appointed time, and Jesus meets it knowingly.

Who is the Son of man, and who are the sinners?

“The Son of man” (huiós, son, and ánthrōpos, man) is the name Jesus most often uses for himself. It speaks of his true humanity, and it is the name of the one to whom Daniel saw dominion, glory and a kingdom given (Daniel 7:13–14). On this night the one with that authority is handed over.

“Is betrayed” is paradídōmi, to give over or hand over. The word can be used of entrusting something, and here it means treachery, a handing over to enemies. A close companion does it, as the psalm had said of the trusted friend who turns against the righteous (Psalm 41:9), and such a betrayal was a deep disgrace in Israel. Jesus had named it at the table (John 13:21), had said that the Son of man goes as it is written of him (Matthew 26:24), and had told the disciples beforehand that he would be betrayed and killed and would rise (Matthew 17:22–23). Peter later preaches that he was delivered up by the settled counsel and foreknowledge of God (Acts 2:23). Judas acts wickedly, and God’s plan stands over the act.

“Into the hands” (eis, into, and cheír, hand) means into the power of others. The “sinners” (hamartōlós) are those who oppose God’s will: the chief priests and elders who plotted to take Jesus (Matthew 26:3–4), and the Roman authorities whose soldiers would mock and crucify him (Matthew 27:27–31). The Holy One is given into the power of the sinful, and he goes for the sake of sinners.

“Rise, let us be going”

Was Jesus trying to escape?

Jesus is going toward his betrayer. Egeírō means to wake or to rise, and here it is a command to men who have been asleep. “Let us be going” includes himself, and the direction is forward, to meet those who are coming. The following verses bring Judas with a great crowd carrying swords and staves, sent by the chief priests and elders, who wanted Jesus taken away from the crowds of the feast (Matthew 26:47–56).

“Behold” comes back from verse 45, and so do “at hand” and “betray”. Jesus knows who is coming and why. The one who lay on his face, sorrowful unto death, now stands and gives orders. The struggle was settled in prayer, and what follows is done in the calm of a will given wholly to the Father.

What Christ’s obedience in the garden won

In Gethsemane the Lamb of God, who takes away the sin of the world (John 1:29), gives himself to be slain. It is Passover, the feast of deliverance from bondage, and the true Passover Lamb is about to win a greater freedom. “Thy will be done” in the garden leads to “It is finished” on the cross (John 19:30). By his own blood he obtained eternal redemption for us (Hebrews 9:12), through the offering of his body once for all (Hebrews 10:10). Behind it all stands the love of God, who gave his only begotten Son so that whoever believes in him should have everlasting life (John 3:16).

What Gethsemane gives us

Gethsemane shows us a Saviour who knows sorrow from the inside. He felt dread and said so, he asked his friends to stay near, and he fell on his face before his Father. Grief and fear in a believer are therefore things he understands, and they can be brought to God in plain words, as his were.

The garden also shows what our salvation cost. The cup was real, and the Son of God looked into it and trembled. He drank it because the Father willed it and because he loved us, so the wrath we deserved has been borne and the cup left to us is the cup of salvation.

His prayer gives us words for our own hardest hours. We may ask for the cup to pass, and ask again, and still say “thy will be done”, trusting that the Father’s will is good even when the road runs through suffering. And where we are like the disciples, willing in spirit and heavy-eyed in the moment, the passage is gentle with us. Jesus named their weakness with understanding, told them where strength is found, and went on to die for them. He gives his Spirit to those who watch and pray, and he keeps the watch himself where we have slept.

Last revised

Historical interpretation

Nine Centuries of Reception

14 surviving comments on this verse. Each one is dated, so this reads as a timeline rather than a list.

14 quotes · AD 220–1107
Ante-NicenePost-NiceneEarly MedievalMedieval
20030040050060070080090010001100

Select a marker to jump to its quote. Markers stagger vertically where authors wrote within a few decades of each other.

d. AD 220TertullianAnte-NiceneSourceOn Flight in Persecution
And for this reason He puts first "the willing spirit," that, looking to the natures respectively of both the substances, you may see that you have in you the spirit's strength as well as the flesh's weakness; and even from this may learn what to do, and by what means to do it, and what to bring under what,-the weak, namely, under the strong, that you may not, as is now your fashion, make excuses on the ground of the weakness of the flesh, forsooth, but put out of sight the strength of the spirit. He also asked of His Father, that if it might be, the cup of suffering should pass from Him. So ask you the like favour; but as He did, holding your position,-merely offering supplication, and adding, too, the other words: "but not what I will, but what Thou wilt.
d. AD 253Origen of Alexandriaas quoted by Aquinas, AD 1274Ante-NiceneSourceCatena Aurea by Aquinas
He took with Him the self-confident Peter, and the others, that they might see Him falling on His face and praying, and might learn not to think great things, but little things of themselves, and not to be hasty in promising, but careful in prayer. And therefore, He went forward a little, not to go far from them, but that He might be near them in His prayer. Also, He who had said above, Learn of me, for I am meek and lowly in heart, now commendably humbling Himself, falls on His face. But He shows His devotion in His prayer, and as beloved and well-pleasing to His Father, He adds, Not as I will, but as thou wilt, teaching us that we should pray, not that our own will, but that God's will, should be done. And as He began to have fear and sorrow, He prays accordingly that the cup of His Passion may pass from Him, yet not as He wills, but as His Father wills; wills, that is, not according to His Divine and impassible Substance, but according to His human and weak nature. For in taking upon Him the nature of human flesh, He fulfilled all the properties thereof, that it might be seen that He had flesh not in appearance only, but in-reality. The believer indeed must in the first instance be loth to incur pain, seeing it leads to death, and he is a man of flesh; but if it be God's will, he acquiesces because he is a believer. For as we ought not to be too confident that we may not seem to make a boast of our own strength; so neither ought we to be distrustful, lest we should seem to charge God our helper with weakness. It is to be observed that Mark and Luke write the same, but John does not introduce this prayer of Jesus', that this cup may pass from Him, because the first three are rather occupied about Him, according to His human nature, John according to His divine. Otherwise; Jesus makes this petition, because He sees what the Jews will suffer for requiring His death.

Then again considering the benefit that would accrue to the whole world from His Passion, He says, But not as I will, but as thou wilt; i. e. If it be possible for all these benefits which shall result from My Passion to be procured without it, let it pass from Me, and both the world be saved, and the Jews not be condemned in putting Me to death. But if the salvation of many cannot be procured without the destruction of a few, saving Thy justice, let it not pass away. Scripture, in many places, speaks of passion as a cup that is drained; and it is drained by him, who in testimony suffers whatever is inflicted upon him. He sheds it, on the contrary, who denies in order to avoid suffering.
His words "if it be possible" referred not only to God's power but also to his justice. As to God's power, whatever is just or unjust is possible. As to his justice, which is not only powerful but also just, not everything is possible—only that which is just.
d. AD 367Hilary of Poitiersas quoted by Aquinas, AD 1274Post-NiceneSourceCatena Aurea by Aquinas
Otherwise; He says not, Let this cup pass away from Me, for that would be the speech of one who feared it; but He prays that it may pass not so as that He should be passed over, but that when it has passed from Him, it may go to another. His whole fear then is for those who were to suffer, and therefore He prays for those who were to suffer after Him, saying, Let this cup pass from me, i. e. as it is drunk by Me, so let it be drunk by these, without mistrust, without sense of pain, without fear of death. He says, If it be possible, because flesh and blood shrink from these things, and it is hard for human bodies not to sink beneath their infliction. That He says, Not as I will, but as thou wilt, He would fain indeed that they should not suffer, lest their faith should fail in their sufferings, if indeed we might attain to the glory of our joint inheritance with Him without the hardship of sharing in His Passion. He says, Not as I will, but as thou wilt, because it is the Father's will that strength to drink of the cup should pass from Him to them, that the Devil might be vanquished not so much by Christ as by His disciples also.

When then He returned to His disciples and found them sleeping, He rebukes Peter, Could ye not watch one hour with me? He addresses Peter rather than the rest, because he had most loudly boasted that he would not be offended.

And why He thus encouraged them to pray that they might not enter into temptation, He adds, For the spirit indeed is willing, but the flesh is weak; this He says not of Himself, but addresses them.

Otherwise, He bare in His own body all the infirmities of us His disciples who should suffer, and nailed to His cross all wherein we are distressed; and therefore that cup cannot pass from Him, unless He drink it, because we cannot suffer, except by His passion.
d. AD 407John Chrysostomas quoted by Aquinas, AD 1274Post-NiceneSourceCatena Aurea by Aquinas
He finds them sleeping, both because it was a late hour of the night, and their eyes were heavy with sorrow.

But as they had all said the same, He charges them all with weakness; they had chosen to die with Christ, and yet could not even watch with Him.

That He prays for this a second and a third time, comes of the feelings belonging to human frailty, through which also He feared death, thus giving assurance that He was truly made man. For in Scripture when any thing is repeated a second and third time, that is the greatest proof of its truth and reality; as, for example, when Joseph says to Pharaoh, And for that thou sawedst it twice, it is proof of the thing being established by God. (Gen. 41:32.)
However, even these He dismisses: "And He went on a little farther, and prayeth, saying, Father, if it be possible, let this cup pass from me; nevertheless not as I will, but as Thou wilt. And He cometh unto them, and findeth them sleeping, and saith unto Peter, What, could ye not watch with me one hour? Watch and pray, that ye enter not into temptation; the spirit indeed is willing, but the flesh is weak."

Not without reason doth He inveigh against Peter most, although the others also had slept; but to make him feel by this also, for the cause which I mentioned before. Then because the others also said the same thing (for when Peter had said (these are the words), "Though I must die with Thee, I will not deny Thee; likewise also," it is added, "said all the disciples"); He addresses Himself to all, convicting their weakness. For they who are desiring to die with Him, were not then able so much as to sorrow with Him wakefully, but sleep overcame them.

And He prays with earnestness, in order that the thing might not seem to be acting. And sweats flow over him for the same cause again, even that the heretics might not say this, that He acts the agony. Therefore there is a sweat like drops of blood, and an angel appeared strengthening Him, and a thousand sure signs of fear, lest any one should affirm the words to be feigned. For this cause also was this prayer. By saying then, "If it be possible, let it pass from me," He showed His humanity; but by saying, "Nevertheless not as I will, but as Thou wilt," He showed His virtue and self-command, teaching us even when nature pulls us back, to follow God. For since it was not enough for the foolish to show His face only, He uses words also. Again, words sufficed not alone, but deeds likewise were needed; these also He joins with the words, that even they who are in a high degree contentious may believe, that He both became man and died. For if, even when these things are so, this be still disbelieved by some, much more, if these had not been. See by how many things He shows the reality of the incarnation: by what He speaks, by what He suffers. After that He cometh and saith to Peter, as it is said, "What, couldest thou not watch one hour with me?" All were sleeping, and He rebukes Peter, hinting at him, in what He spake. And the words, "with me," are not employed without reason; it is as though He had said, Thou couldest not watch with me one hour, and wilt thou lay down thy life for me? and what follows also, intimates this self-same thing. For "Watch," saith He, "and pray not to enter into temptation." See how He is again instructing them not to be self-confident, but contrite in mind, and to be humble, and to refer all to God.

And at one time He addresses Himself to Peter, at another to all in common. And to him He saith, "Simon, Simon, Satan hath desired to have you, that he may sift you as wheat; but I have prayed for thee;" and to all in common, "Pray that ye enter not into temptation;" every way plucking up their self-will, and making them earnest-minded. Then, that He might not seem to make His language altogether condemnatory, He saith, "The spirit indeed is ready, but the flesh is weak." For even although thou dost desire to despise death, yet thou wilt not be able, until God stretch forth His hand, for the carnal mind draws down.

And again He prayed in the same way, saying, "Father, if this cannot pass from me except I drink it, Thy will be done," showing here, that He fully harmonizes with God's will, and that we must always follow this, and seek after it.
d. AD 420JeromePost-NiceneSourceCommentary on Matthew
(Verse 39) And going forward a little, he fell on his face, praying and saying: My Father, if it is possible, let this cup pass away from me. Nevertheless, not as I will, but as you will. Having given the apostles the command to endure and keep watch with the Lord, he advanced a little and fell on his face, showing the humility of his mind in the appearance of his flesh, and he said in a gentle way: My Father, and he asked that, if possible, the cup of suffering pass from him, about which we have spoken above. But, he does not ask to be spared out of fear, but out of mercy for the earlier people, so as not to drink from the cup that they have offered. Therefore, he specifically does not say, let this cup pass from me, but let this cup pass, that is, the cup of the Jewish people, who cannot claim ignorance as an excuse, if they kill me, having the Law and the prophets, who daily prophesy about me. Yet, turning back to himself, what he had hesitantly declined from the perspective of a human, he confirms from the perspective of God the Son. However, not as I want, but as you. No, he says, let this not be done, which I speak with human emotion; but because of what I descended to earth by your will.
d. AD 420Jeromeas quoted by Aquinas, AD 1274Post-NiceneSourceCatena Aurea by Aquinas
Or the sleep which He would have them forego is not bodily rest, for which at this critical time there was no room, but mental torpor, the sleep of unbelief.

Whence He says emphatically, This cup, that is, of this people of the Jews, who, if they shall put Me to death, can have no excuse for their ignorance, seeing they have the Law and the Prophets, who speak of Me.

It is impossible that the human mind should not be tempted, therefore He says not Watch and pray that ye be not tempted, but that ye enter not into temptation, that is, that temptation vanquish you not.

This is against those rash persons who think that whatever they believe they can perform. The more confident we are of our zeal, the more mistrustful should we be of the frailty of the flesh.

Or otherwise; He prays a second time that if Nineveh, or the Gentile world, cannot be saved unless the gourd, i. e. the Jews, be withered, His Father's will may be done, which is not contrary to the Son's will, who Himself speaks by the Prophet, I am content to do thy will, O God. (Ps. 40:8.)

Christ singly prays for all, as He singly suffers for all. Their eyes were heavy, i. e. an oppression and stupefaction came on as their denial drew near.

He prayed the third time, that in the mouth of two or three witnesses every word might be established.
d. AD 430Augustine of Hippoas quoted by Aquinas, AD 1274Post-NiceneSourceCatena Aurea by Aquinas
(de Cons. Ev. iii. 4.) And that none might think that He limited His Father's power, He said not, If thou canst do it, but If it may be, or, If it be possible; as much as to say, If thou wilt. For whatever God wills can be done, as Luke expresses more plainly; for he says not, If it be possible, but If thou wilt.

(in Ps. 32. enar. 2.) Christ thus as man shows a certain private human will, in which He who is our head figures both His own will and ours when He says, Let it pass from me. For this was His human will choosing something as apart for Himself. But because as man He would be righteous and guide Himself by God's will, He adds, Nevertheless not as I will, but as thou wilt; as much as to say to us, Man, behold thyself in Me, that thou canst will somewhat apart of thyself, and though God's will is other, this is permitted to human frailty.

(Quaest. Ev. i. 47.) Nor is that an absurd interpretation which makes Our Lord pray thrice because of the threefold temptation of His Passion. To the temptation of curiosity is opposed the fear of death; for as the one is a yearning for the knowledge of things, so the other is the fear of losing such knowledge. To the desire of honour or applause is opposed the dread of disgrace and insult. To the desire of pleasure is opposed the fear of pain.
d. AD 461Leo the GreatPost-NiceneSourceSERMON 43.2.26
The disciples were admonished, and the Lord beseeches the Father that they might confront the force of the present temptation with watchful prayer: “My Father, if it be possible, let this cup pass from me; nevertheless not as I will, but as you will.” The first petition arises from weakness, the second from strength: He desired the former based on our nature and chose the latter based on his own. Equal to the Father, the Son knew that all things were possible to God; rather, he descended into this world to take up the cross against his will so that he might suffer through this conflict of emotions with a disquieted mind. But in order to show the distinction between the receiving nature and the received nature, what was proper of humanity desired divine intervention and what was proper of God looked upon the human situation. The lower will yielded to the higher will, and this demonstrated what the fearful person may pray for and what the divine healer should not grant. “For we do not know how to pray as we ought,” and it is good for us that what we want, for the most part, is not granted. God, who is good and just, shows mercy toward us by denying us those things we ask for which are harmful.
d. AD 461Leo the Greatas quoted by Aquinas, AD 1274Post-NiceneSourceCatena Aurea by Aquinas
(Serm. 58, 5.) This speech of the Head is the health of the whole body, this saying is instruction to the faithful, animates the confessor, crowns the martyr. For who could vanquish the hatred of the world, or the whirlwind of temptations, or the terrors of the persecutors, if Christ did not in all and for all say to the Father, Thy will be done. Let all the sons of the Church then utter this prayer, that when the pressure of some mighty temptation lies upon them, they may embrace endurance of the suffering, disregarding its terrors.
d. AD 533Remigius of Rheimsas quoted by Aquinas, AD 1274Post-NiceneSourceCatena Aurea by Aquinas
Otherwise; In these words He shows that He took real flesh of the Virgin, and had a real soul, saying that His spirit is willing to suffer, but His flesh weak in fearing the pain of Passion.

Or, He prays thrice for the Apostles, and for Peter in particular, who was to deny Him thrice.
d. AD 856Rabanus Maurusas quoted by Aquinas, AD 1274Early MedievalSourceCatena Aurea by Aquinas
Or, The Lord prayed thrice, to teach us to pray for pardon of sins past, defence against present evil, and provision against future perils, and that we should address every prayer to Father, Son, and Holy Spirit, and that our spirit, soul, and body should be kept in safety.
d. AD 1107Theophylact of OhridMedieval
. He does not take all the disciples with Him, but only the three to whom He showed His glory on Mt. Tabor, lest the others see Him very heavy of heart while He was praying, and be scandalized. But He leaves even these three and goes away to a place to pray that was yet more private. He was sorrowful and heavy in accord with the divine plan, so as to confirm that He was truly man. For it is human nature to fear death; it was against our nature that death entered, and for this reason our nature flees from it. At the same time, Christ was sorrowful so that the devil would unknowingly leap upon Him, the God-man, and bear Him down to death as though He were mere man, and thus the devil himself would be crushed. Moreover, if the Lord had rushed towards death it would have given the Jews the excuse that they did not sin in killing one who was so eager to suffer. From this we learn not to throw ourselves into trials and temptations, but to pray that we may be delivered from them. For this reason, too, He did not move away a great distance, but was near the three disciples, that they might hear Him and remember when they themselves fell into temptations, and pray in the same manner. He calls His Passion a cup [as of wine], either because of the sleep which it brought, or because it became the cause of gladness and salvation for us. He wants the cup to be removed either to show that as a man subject to nature He pleads to escape death, as was said above, or because He did not wish the Jews to commit a sin so grave that on account of it the temple would be destroyed and the people perish. Yet He desires that His Father’s will be done, that we also may learn that it is precisely when our nature draws us away from obedience that we must obey God and fulfill His will.
Source: Quotations drawn from early Church Fathers and historical Christian theologians (AD 100–1500). Some quotes address the surrounding passage context rather than this verse alone.

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