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Translation
King James Version
But Jesus said unto them, Ye know not what ye ask: can ye drink of the cup that I drink of? and be baptized with the baptism that I am baptized with?
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KJV (with Strong's)
But G1161 Jesus G2424 said G2036 unto them G846, Ye know G1492 not G3756 what G5101 ye ask G154: can ye G1410 drink G4095 of the cup G4221 that G3739 I G1473 drink of G4095? and G2532 be baptized G907 with the baptism G908 that G3739 I G1473 am baptized with G907?
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Complete Jewish Bible
But Yeshua answered, "You don't know what you're asking! Can you drink the cup that I am drinking? or be immersed with the immersion that I must undergo?"
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Berean Standard Bible
“You do not know what you are asking,” Jesus replied. “Can you drink the cup I will drink, or be baptized with the baptism I will undergo?”
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American Standard Version
But Jesus said unto them, Ye know not what ye ask. Are ye able to drink the cup that I drink? or to be baptized with the baptism that I am baptized with?
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World English Bible Messianic
But Yeshua said to them, “You don’t know what you are asking. Are you able to drink the cup that I drink, and to be immersed with the immersion that I am immersed with?”
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Geneva Bible (1599)
But Iesus sayd vnto them, Ye knowe not what ye aske. Can ye drinke of the cup that I shall drinke of, and be baptized with the baptisme that I shall be baptized with?
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Young's Literal Translation
and Jesus said to them, `Ye have not known what ye ask; are ye able to drink of the cup that I drink of, and with the baptism that I am baptized with--to be baptized?'
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In the KJVVerse 24,627 of 31,102

Study This Verse

SUMMARY

In Mark 10:38, Jesus confronts the ambitious request of James and John, who sought positions of glory in His kingdom, by challenging their understanding of true discipleship. He reveals that the path to glory for Him, and for His followers, involves a profound immersion in suffering and sacrifice, symbolized by a "cup" and a "baptism," thereby correcting their worldly perception of His messianic mission.

CONTEXT

  • Literary Context: This verse is a direct response to the audacious request made by James and John, the sons of Zebedee, in Mark 10:37. They ask to sit at Jesus' right and left hand in His glory, indicating a profound misunderstanding of the nature of His kingdom and His impending suffering. This episode immediately follows Jesus' third prediction of His passion, death, and resurrection in Mark 10:32-34, which the disciples clearly failed to grasp. The subsequent reaction of the other ten disciples (Mark 10:41) highlights the pervasive struggle among them to comprehend Jesus' servant leadership model, culminating in Jesus' teaching on servanthood and ransom in Mark 10:42-45.
  • Historical & Cultural Context: First-century Judaism was deeply steeped in messianic expectation, often envisioning a political Messiah who would overthrow Roman rule and establish an earthly kingdom with Jerusalem as its capital. The disciples, sharing this common cultural framework, likely anticipated a glorious, triumphant reign where they, as Jesus' closest followers, would hold positions of power and prestige. Their request reflects this deeply ingrained hope for national restoration and personal elevation. They struggled to reconcile Jesus' teachings on suffering and humility with their preconceived notions of a conquering king, failing to grasp the spiritual, redemptive, and suffering nature of His true kingdom, which would be inaugurated through His death and resurrection, not through political conquest.
  • Key Themes: This verse powerfully contributes to several overarching themes in Mark's Gospel. Firstly, it underscores the misunderstanding of discipleship, revealing the disciples' persistent struggle to grasp the true nature of following Jesus, which involves self-denial and suffering rather than earthly power. Secondly, it highlights the cost of following Christ, emphasizing that genuine discipleship requires a willingness to share in Jesus' suffering and sacrifice, not merely His future glory. Jesus' questions serve as a stark reminder that His path to glory is through the cross, a path His followers are also called to walk. Thirdly, it functions as a subtle yet profound prophecy of suffering, with Jesus alluding to His impending passion and death, which He had already foretold in Mark 8:31 and Mark 9:31. The "cup" and "baptism" become powerful metaphors for the agony and immersion in suffering He was about to endure for humanity's salvation.

EXPOSITION AND ANALYSIS

Key Word Analysis

  • know (Greek, eídō', G1492): A primary verb meaning "to see (literally or figuratively); by implication, (in the perfect tense only) to know." Jesus' statement "Ye know not what ye ask" indicates a profound lack of spiritual discernment on the part of James and John. They "see" only the outward glory and power they desire, but do not "know" or comprehend the immense suffering and sacrifice that must precede it, both for Jesus and for those who truly follow Him. Their request stems from ignorance of the true nature of the Messiah's mission and the cost of kingdom participation.
  • cup (Greek, potḗrion', G4221): A neuter noun meaning "a drinking-vessel; by extension, the contents thereof, i.e. a cupful (draught); figuratively, a lot or fate." In biblical imagery, a "cup" often symbolizes a person's destiny or allotted portion, particularly one of suffering, wrath, or judgment. For Jesus, this cup represents the full measure of suffering He would endure, including the agony of Gethsemane, the betrayal, the trial, the crucifixion, and the bearing of the world's sin and God's wrath against it.
  • baptized (Greek, baptízō', G907): A verb meaning "to immerse, submerge; to make whelmed (i.e. fully wet); used only (in the New Testament) of ceremonial ablution, especially (technically) of the ordinance of Christian baptism." Here, Jesus uses "baptism" metaphorically to signify an overwhelming immersion in suffering, affliction, and ultimately death. It speaks of being completely submerged or overwhelmed by trials and tribulations, specifically His impending agony and death on the cross.

Verse Breakdown

  • "But Jesus said unto them, Ye know not what ye ask": Jesus immediately addresses the core issue: James and John's profound ignorance regarding the nature of His kingdom and the path to glory. Their request for preeminence stems from a worldly perspective, completely missing the spiritual and sacrificial essence of discipleship. They desire the crown without understanding the cross that precedes it.
  • "can ye drink of the cup that I drink of?": This is a powerful rhetorical question. The "cup" symbolizes the intense suffering and divine wrath that Jesus, as the sin-bearer, would fully experience. It refers to His passion, His Gethsemane agony, and His atoning death on the cross. Jesus challenges them: are you truly prepared to endure such a destiny, to partake in the very depth of suffering that awaits Me?
  • "and be baptized with the baptism that I am baptized with?": This second rhetorical question reinforces the first, using another vivid metaphor. The "baptism" here signifies an overwhelming immersion in suffering, affliction, and death. Jesus is asking if they are willing to be completely submerged in the trials and tribulations that He is about to undergo, a "baptism" of agony that would culminate in His death and burial. Both metaphors point to the same reality: the path to true glory in God's kingdom is through profound suffering and self-sacrifice.

Literary Devices

Mark 10:38 employs several potent Literary Devices. The most prominent are Metaphor and Rhetorical Question. Jesus uses the Metaphor of "the cup" and "the baptism" to represent His impending suffering and death. The "cup" is a common biblical image for one's allotted destiny, often involving divine judgment or intense suffering (e.g., Psalm 75:8, Isaiah 51:17). The "baptism" here is not water baptism but a metaphorical immersion in overwhelming suffering (as seen in Luke 12:50). These metaphors powerfully convey the depth and nature of the agony Jesus was about to face. The entire verse is structured as a series of Rhetorical Questions, "can ye drink of the cup...?" and "and be baptized with the baptism...?" These questions are not posed to elicit a literal "yes" or "no" answer, but to provoke deep introspection and reveal the disciples' ignorance. They serve to highlight the stark contrast between the disciples' worldly ambitions and the true, sacrificial nature of Jesus' mission and the path of discipleship. There is also an element of Irony, as James and John's ambitious request for glory is met with a challenge to embrace suffering, revealing the ironic truth that true glory in God's kingdom comes through self-denial.

THEOLOGICAL AND THEMATIC CONNECTIONS

Mark 10:38 is a profound theological statement on the nature of discipleship and the kingdom of God. It shatters the common misconception that following Christ leads primarily to earthly power and prestige, redirecting focus to the path of suffering and self-sacrifice. Jesus' questions reveal that genuine participation in His kingdom is not about receiving honor, but about sharing in His mission, which, for Him, involved bearing the weight of sin and experiencing profound agony. For believers, this means a willingness to endure hardship, persecution, and self-denial for the sake of the Gospel, understanding that our suffering for Christ's sake is a form of fellowship with Him and a prelude to future glory. It underscores that the cross is central to both Christ's work and the believer's journey.

REFLECTION AND APPLICATION

Mark 10:38 serves as a timeless challenge to every follower of Jesus, urging us to deeply examine our motives for discipleship. Are we drawn to Christ for the promise of comfort, prosperity, or social status, or are we prepared to embrace the full scope of what it means to walk in His footsteps, which often includes hardship, sacrifice, and even suffering for the sake of the Gospel? This verse calls us to align our desires with God's will, understanding that true honor in the kingdom comes through humility and service, not through self-seeking ambition. It reminds us that the cross is not merely an historical event but a pattern for our lives, inviting us to daily deny ourselves, take up our cross, and follow Him, trusting that even in suffering, God is at work, conforming us to the image of His Son and preparing us for eternal glory.

Questions for Reflection

  • What are my true motivations for following Jesus? Am I seeking personal gain or a deeper commitment to His mission, even if it involves sacrifice?
  • In what ways might I be asking for "glory" without understanding the "cup" or "baptism" of suffering that accompanies true discipleship?
  • How can I cultivate a greater willingness to embrace hardship or self-denial for the sake of Christ and His kingdom?

FAQ

What is the significance of Jesus' references to "cup" and "baptism" in this verse?

Answer: Jesus' references to "the cup that I drink of" and "the baptism that I am baptized with" are powerful metaphors for His impending suffering, death, and the divine wrath He would endure as the sin-bearer. The "cup" in biblical imagery often represents a person's destiny or allotted portion, particularly one of suffering or judgment, as seen in passages like Psalm 75:8 and Isaiah 51:17. For Jesus, this cup represents the full agony of His passion, including Gethsemane and the cross, where He would bear the sins of the world. The "baptism" similarly refers not to water baptism but to an overwhelming immersion in suffering, affliction, and ultimately death. Jesus uses this metaphor elsewhere, stating, "I have a baptism to be baptized with; and how am I straitened till it be accomplished!" in Luke 12:50. Both metaphors underscore the immense, overwhelming nature of the suffering Jesus was about to face, which was necessary for the redemption of humanity.

CHRIST-CENTERED FULFILLMENT

Mark 10:38 profoundly points to Christ's unique and ultimate fulfillment of the "cup" of suffering and the "baptism" of death. Jesus' question to James and John was not merely rhetorical; it foreshadowed the very path He was about to tread. The "cup" He would drink was the cup of God's wrath against sin, which He alone could fully drain, as evidenced by His agonizing prayer in Gethsemane, "O my Father, if it be possible, let this cup pass from me: nevertheless not as I will, but as thou wilt" (Matthew 26:39). This cup represents the full measure of divine judgment for sin, a burden no human could bear. Similarly, the "baptism" He was to be baptized with was His complete immersion into death, burial, and the depths of human suffering, culminating in His atoning sacrifice on the cross. This was the ultimate act of obedience and love, through which He became the Lamb of God who takes away the sin of the world (John 1:29). While believers are called to share in Christ's sufferings (Philippians 3:10) through persecution, self-denial, and perseverance, our suffering is never redemptive or atoning. It is Christ's solitary drinking of the cup and His unique baptism into death that secured our salvation, making Him the pioneer and perfecter of our faith, who for the joy set before Him endured the cross (Hebrews 12:2). His journey through suffering to glory is the prototype for all who follow Him, yet His atoning work remains exclusively His own.

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Commentary on Mark 10 verses 32–45

I. II. Main points1. 2. Sub-points

Here is, I. Christ's prediction of his own sufferings; this string he harped much upon, though in the ears of his disciples it sounded very harsh and unpleasing.

1.See here how bold he was; when they were going up to Jerusalem, Jesus went before them, as the captain of our salvation, that was now to be made perfect through sufferings, Mar 10:32. Thus he showed himself forward to go on with his undertaking, even when he came to the hardest part of it. Now that the time was at hand, he said, Lo, I come; so far was he from drawing back, that now, more than ever, he pressed forward. Jesus went before them, and they were amazed. They began now to consider what imminent danger they ran themselves into, when they went to Jerusalem; how very malicious the Sanhedrim which sat there was against their Master and them; and they were ready to tremble at the thought of it. To hearten them, therefore, Christ went before them. "Come," saith he, "surely you will venture where your Master ventures." Note, When we see ourselves entering upon sufferings, it is encouraging to see our Master go before us. Or, He went before them, and therefore they were amazed; they admired to see with what cheerfulness and alacrity he went on, though he knew he was going to suffer and die. Note, Christ's courage and constancy in going on with his undertaking for our salvation, are, and will be, the wonder of all his disciples.

2.See here how timorous and faint-hearted his disciples were; As they followed, they were afraid, afraid for themselves, as being apprehensive of their own danger; and justly might they be ashamed of their being thus afraid. Their Master's courage should have put spirit into them.

3.See here what method he took to silence their fears. He did not go about to make the matter better than it was, nor to feed them with hopes that he might escape the storm, but told them again what he had often told them before, the things that should happen to him. He knew the worst of it, and therefore went on thus boldly, and he will let them know the worst of it. Come, be not afraid; for, (1.) There is no remedy, the matter is determined, and cannot be avoided. (2.) It is only the Son of man that shall suffer; their time of suffering was now at hand, he will now provide for their security. (3.) He shall rise again; the issue of his sufferings will be glorious to himself, and advantageous to all that are his, Mar 10:33, Mar 10:34. The method and particulars of Christ's sufferings are more largely foretold here than in any other of the predictions - that he shall first be delivered up by Judas to the chief priests and the scribes; that they shall condemn him to death, but, not having the power to put him to death, shall deliver him to the Gentiles, to the Roman powers, and they shall mock him, and scourge him, and spit upon him, and kill him. Christ had a perfect foresight, not only of his own death, but of all the aggravating circumstances of it; and yet he thus went forth to meet it.

II. The check he gave to two of his disciples for their ambitious request. This story is much the same here as we had it Mat 20:20. Only there they are said to have made their request by their mother, here they are said to make it themselves; she introduced them, and presented their petition, and then they seconded it, and assented to it.

Note, 1. As, on the one hand, there are some that do not use, so, on the other hand, there are some that abuse, the great encouragements Christ has given us in prayer. He hath said, Ask, and it shall be given you; and it is a commendable faith to ask for the great things he has promised; but it was a culpable presumption in these disciples to make such a boundless demand upon their Master; We would that thou shouldest do for us whatsoever we shall desire. We had much better leave it to him to do for us what he sees fit, and he will do more than we can desire, Eph 3:20.

2.We must be cautious how we make general promises. Christ would not engage to do for them whatever they desired, but would know from them what it was they did desire; What would ye that I should do for you? He would have them go on with their suit, that they might be made ashamed of it.

3.Many have been led into a snare by false notions of Christ's kingdom, as if it were of this world, and like the kingdoms of the potentates of this world. James and John conclude, If Christ rise again, he must be a king, and if he be a king, his apostles must be peers, and one of these would willingly be the Primus par regni - The first peer of the realm, and the other next him, like Joseph in Pharaoh's court, or Daniel in Darius's.

4.Worldly honour is a glittering thing, with which the eyes of Christ's own disciples have many a time been dazzled. Whereas to be good should be more our care than to look great, or to have the pre-eminence.

5.Our weakness and short-sightedness appear as much in our prayers as in any thing. We cannot order our speech, when we speak to God, by reason of darkness, both concerning him and concerning ourselves. It is folly to prescribe to God, and wisdom to subscribe.

6.It is the will of Christ that we should prepare for sufferings, and leave it to him to recompense us for them. He needs not be put in mind, as Ahasuerus did, of the services of his people, nor can he forget their work of faith and labour of love. Our care must be, that we may have wisdom and grace to know how to suffer with him, and then we may trust him to provide in the best manner how we shall reign with him, and when, and where, and what, the degrees of our glory shall be.

III. The check he gave to the rest of the disciples, for their uneasiness at it. They began to be much displeased, to have indignation about James and John, Mar 10:41. They were angry at them for affecting precedency, not because it did so ill become the disciples of Christ, but because each of them hoped to have it himself. When the Cynic trampled on Alexander's foot-cloth, with Calco fastum Alexandri - Now I tread on Alexander's pride, he was seasonably checked with Sed majori fastu - But with a greater pride of thine own. So these discovered their own ambition, in their displeasure at the ambition of James and John; and Christ took this occasion to warn them against it, and all their successors in the ministry of the gospel, Mar 10:42-44. He called them to him in a familiar way, to give them an example of condescension, then when he was reproving their ambition, and to teach them never to bid their disciples keep their distance. He shows them,

1.That dominion was generally abused in the world (Mar 10:42); That they seemed to rule over the Gentiles, that have the name and title of rulers, they exercise lordship over them, that is all they study and aim at, not so much to protect them, and provide for their welfare, as to exercise authority upon them; they will be obeyed, aim to be arbitrary, and to have their will in every thing. Sic volo, sic jubeo, stat pro ratione voluntas - Thus I will, thus I command; my good pleasure is my law. Their care is, what they shall get by their subjects to support their own pomp and grandeur, not what they shall do for them.

2.That therefore it ought not to be admitted into the church; "It shall not be so among you; those that shall be put under your charge, must be as sheep under the charge of the shepherd, who is to tend them and feed them, and be a servant to them, not as horses under the command of the driver, that works them and beats them, and gets his pennyworths out of them. He that affects to be great and chief, that thrusts himself into a secular dignity and dominion, he shall be servant of all, he shall be mean and contemptible in the eyes of all that are wise and good; he that exalteth himself shall be abased." Or rather, "He that would be truly great and chief, he must lay out himself to do good to all, must stoop to the meanest services, and labour in the hardest services. Those not only shall be most honoured hereafter, but are most honourable now, who are most useful." To convince them of this, he sets before them his own example (Mar 10:45); "The Son of man submits first to the greatest hardships and hazards, and then enters into his glory, and can you expect to come to it any other way; or to have more ease and honour than he has?" (1.) He takes upon him the form of a servant, comes not to be ministered to, and waited upon, but to minister, and wait to be gracious. (2.) He comes obedient to death, and to its dominion, for he gives his life a ransom for many; did he die for the benefit of good people, and shall not we study to live for their benefit?

Matthew Henry (1662–1714) — Commentary on the Whole Bible. This section covers verses 32–45. Public domain.
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Polycarp of SmyrnaAD 155
Martyrdom of Polycarp 14
And he, placing his hands behind him, and being bound like a distinguished ram [taken] out of a great flock for sacrifice, and prepared to be an acceptable burnt-offering unto God, looked up to heaven, and said, "O Lord God Almighty, the Father of thy beloved and blessed Son Jesus Christ, by whom we have received the knowledge of Thee, the God of angels and powers, and of every creature, and of the whole race of the righteous who live before thee, I give Thee thanks that Thou hast counted me, worthy of this day and this hour, that I should have a part in the number of Thy martyrs, in the cup of thy Christ, to the resurrection of eternal life, both of soul and body, through the incorruption [imparted] by the Holy Ghost. Among whom may I be accepted this day before Thee as a fat and acceptable sacrifice, according as Thou, the ever-truthful God, hast fore-ordained, hast revealed beforehand to me, and now hast fulfilled. Wherefore also I praise Thee for all things, I bless Thee, I glorify Thee, along with the everlasting and heavenly Jesus Christ, Thy beloved Son, with whom, to Thee, and the Holy Ghost, be glory both now and to all coming ages. Amen."
Martyrdom Of PolycarpAD 200
Or sacrifice, and prepared to be an acceptable burnt-offering unto God, looked up to heaven, and said, "O Lord God Almighty, the Father of thy beloved and blessed Son Jesus Christ, by whom we have received the knowledge of Thee, the God of angels and powers, and of every creature, and of the whole race of the righteous who live before thee, I give Thee thanks that Thou hast counted me, worthy of this day and this hour, that I should have a part in the number of Thy martyrs, in the cup
IrenaeusAD 202
Against Heresies Book I
Moreover, they affirm that the Lord added this redemption to the sons of Zebedee, when their mother asked that they might sit, the one on His right hand, and the other on His left, in His kingdom, saying, "Can ye be baptized with the baptism which I shall be baptized with? "
Hippolytus of RomeAD 235
Hippolytus Refutation of All Heresies Book V
This is, he says, the great and ineffable mystery of the Samothracians, which it is allowable, he says, for us only who are initiated to know. For the Samothracians expressly hand down, in the mysteries that are celebrated among them, that (same) Adam as the primal man. And habitually there stand in the temple of the Samothracians two images of naked men, having both hands stretched aloft towards heaven, and their pudenda erecta, as with the statue of Mercury on Mount Cyllene. And the aforesaid images are figures of the primal man, and of that spiritual one that is born again, in every respect of the same substance with that man. This, he says, is what is spoken by the Saviour: "If ye do not drink my blood, and eat my flesh, ye will not enter into the kingdom of heaven; but even though," He says, "ye drink of the cup which I drink of, whither I go, ye cannot enter there." For He says He was aware of what sort of nature each of His disciples was, and that there was a necessity that each of them should attain unto His own peculiar nature. For He says He chose twelve disciples from the twelve tribes, and spoke by them to each tribe. On this account, He says, the preachings of the twelve disciples neither did all hear, nor, if they heard, could they receive. For the things that are not according to nature, are with them contrary to nature.
John ChrysostomAD 407
ON THE INCOMPREHENSIBLE NATURE OF GOD 8.32-33
Do you see? They did not understand what they were asking for when they were talking to him about crowns and rewards and the privilege of the first seats and honors even before the contest had begun. Christ was communicating with them on two levels when he said: “You do not know what you are asking for.” One was that they were talking about an earthly kingdom and he had said nothing about this. There had been no announcement or promise about a visible kingdom on earth. The other was that, when they sought at this time the privilege of the first seats and the honors of heaven, when they wished to be seen as more illustrious and splendid than the others, they were not asking for these things at the right time. The timing was precisely wrong. For this was not the right time for crowns or prizes. It was the time for struggles, contests, toils, sweat, wrestling rings and battles.
John ChrysostomAD 407
HOMILIES ON JOHN 25.2
For when we immerse our heads in the water, the old humanity is buried as in a tomb below, and wholly sunk forever. Then as we raise them again, the new humanity rises in its place. As it is easy for us to dip and to lift our heads again, so it is easy for God to bury the old humanity, and to lift up and display the new. And this is done three times, that you may learn that the power of the Father, the Son and the Holy Ghost fulfills all this.
John Chrysostom (as quoted by Aquinas, AD 1274)AD 407
Catena Aurea by Aquinas
(v. Chrys. ubi sup.) The disciples hearing Christ oftentimes speaking of His kingdom, thought that this kingdom was to be before His death, and therefore now that His death was foretold to them, they came to Him, that they might immediately be made worthy of the honours of the kingdom: wherefore it is said, And James and John, the sons of Zebedee, came unto him, saying, Master, we would that thou shouldest do for us whatsoever we shall desire. For ashamed of the human weakness which they felt, they came to Christ, taking Him apart from the disciples; but our Saviour, not from ignorance of what they wanted to ask, but from a wish of making them answer Him, puts this question to them; And he said unto them, What would ye that I should do for you?

(ubi sup.) Or we may fitly say that both took place; for seeing themselves honoured above the rest, they thought that they could easily obtain the foregoing petition; and that they might the more easily succeed in their request, they took their mother with them, that they might pray unto Christ together with her.

(ubi sup.) Or else He says, Ye know not what ye ask; as if He said, Ye speak of honours, but I am discoursing of wrestlings and toil; for this is not a time of rewards, but of blood, of battles, and dangers. Wherefore He adds, Can ye drink of the cup that I drink of, and be baptized with the baptism that I am baptized withal? He draws them on by way of question, that by communication with Himself, their eagerness might increase.

(ubi sup.) And they answered thus quickly, because they expected that what they had asked would be listened to; it goes on: And Jesus said unto them, Ye shall indeed drink of the cup that I drink of, and with the baptism that I am baptized withal shall ye be baptized; t at is, ye shall be worthy of martyrdom, and suffer even as I.

(ubi sup.) Where two questions are raised, one is, whether a seat on His right hand is prepared for any one; the other, whether the Lord of all has it not in His power to give it to those for whom it is prepared. To the first then we say, that no one sits on His right hand or on His left, for that throne is inaccessible to a creature. How then did He say, To sit on my right hand or on my left is not mine to give you, as though it belonged to some who were to sit there? He however answers the thoughts of those who asked Him, condescending to their meaning; for they did not know that lofty throne and seat, which is on the right hand of the Father, but sought one thing alone, that is, to possess the chief place, and to be set over others. And since they had heard it said of the Apostles, that they were to sit on twelve thrones, they begged for a place higher than all the rest, not knowing what was said. To the second question we must say, that such a gift does not transcend the power of the Son of God, but what is said by Matthew (Matt. 20:23), it is prepared by My Father, is the same as if it were said, "by Me," wherefore also Mark did not say here, by My Father. What therefore Christ says here is this, Ye shall die, He says, for Me, but this is not enough to enable you to obtain the highest place, for if another person comes possessing besides martyrdom all other virtues, he will possess much more than you; for the chief place is prepared for those, who by works are enabled to become the first. Thus then the Lord instructed them not to trouble themselves vainly and absurdly for high places; at the same time He would not have them made sad.
John ChrysostomAD 407
ON THE INCOMPREHENSIBLE NATURE OF GOD 8.35
Here Christ was calling his crucifixion a cup and his death a baptism. He called his cross a cup because he was coming to it with pleasure. He called his death a baptism because by it he cleansed the world. Not only on this account did he call his death a baptism but also because of the ease with which he would rise again. For just as one who is baptized in water easily rises up because the nature of the water poses no hindrance, so, too, Christ rose with greater ease because he had gone down into death. And this is why he calls his death a baptism.
John ChrysostomAD 407
THE GOSPEL OF ST MATTHEW, HOMILY 65
This he calls a baptism, showing that from it the whole world would receive a great purification. Then they say to him: “We can.” In the fervor of their spirit they promise immediately, not knowing what they said, but looking to obtain that which they were asking.… He foretold great things for them; that is, you shall be held worthy of martyrdom, you shall suffer the things I have suffered, you shall end your life with a death from violence, and in this also you shall be sharers with me.
Augustine of HippoAD 430
TRACTATE ON JOHN 28.5.2
He meant, of course, the cup of humility and suffering.
Augustine of Hippo (as quoted by Aquinas, AD 1274)AD 430
Catena Aurea by Aquinas
(ubi sup.) Then the Lord both according to Mark, and to Matthew, answered them rather than their mother. For it goes on, But Jesus said unto them, Ye know not what ye ask.
Gregory the DialogistAD 604
Forty Gospel Homilies, Homily 27
There follows: "You are my friends." O how great is the mercy of our Creator! We are not worthy to be servants, and we are called friends. How great is the dignity of men to be friends of God! But you have heard the glory of this dignity; hear also the labor of the struggle: "If you do what I command you." "You are my friends, if you do what I command you." As if He were saying openly: You rejoice at the height; consider by what labors one arrives at the height. Surely when the sons of Zebedee, through the intervention of their mother, sought that one should sit at the right hand of God and the other at the left, they heard: "Can you drink the cup that I am about to drink?" They were already seeking the place of exaltation; the Truth calls them back to the way by which they might come to exaltation. As if it were said: The place of exaltation already delights you, but first let the way of labor exercise you. Through the cup one reaches majesty. If your mind desires what pleases, first drink what causes pain. Thus, thus through the bitter cup of affliction one arrives at the joy of salvation.
BedeAD 735
On the Gospel of Mark
You know not what you ask. Can you drink of the cup that I drink of, or be baptized with the baptism wherewith I am baptized? And they said to him: We can. They know not what they ask, who seek from the Lord the seat of glory which they had not yet deserved. Indeed, the summit of honor was already pleasing to them, but first they had to traverse the path of labor. They desired to reign on high with Christ, but first they had to suffer humbly for Christ. For by the term of the cup or baptism, he designates the passion of martyrdom, through which it became fitting for both him and them to be perfected. Hence, elsewhere, he speaks of his passion: But I have a baptism to be baptized with, and how am I straitened until it be accomplished (Luke 12)? And as he approached his passion, he prayed, saying: Father, if thou wilt, remove this cup from me (Mark 14).
Bede (as quoted by Aquinas, AD 1274)AD 735
Catena Aurea by Aquinas
(ubi sup.) Or else, they know not what they ask, who seek from the Lord a seat of glory, which they do not yet merit.

(ubi sup.) A question is raised, however, how James and John drank the cup of martyrdom, or how they were baptized with the baptism of the Lord, when the Scripture relates, that only James the Apostle was beheaded by Herod whilst John finished his life by a natural death. But if we read ecclesiastical histories, in which it is related, that he also on account of the witness which he bore was cast into a cauldron of burning oil, and was immediately sent away to the island of Patmos, we shall then see that the spirit of martyrdom was in him, and that John drank the cup of confession, which the Three Children also drank in the furnace of fire, though the persecutor did not spill their blood. It goes on: But to sit on my right hand and on my left hand is not mine to give, but it shall be given to them for whom it is prepared.

(ubi sup.) Or else, it is not mine to give to you, that is, to proud persons, for such as yet they were. It is prepared for other persons, and be ye other, that is, lowly, and it is prepared for you.
Theophylact of Ohrid (as quoted by Aquinas, AD 1274)AD 1107
Catena Aurea by Aquinas
Now the abovementioned disciples thought that He was going up to Jerusalem, to reign there, and then to suffer what He had foretold. And with these thoughts, they desired to sit on the right and the left hand; wherefore there follows, They said unto him, Grant unto us that we may sit, one on thy right hand, the other on thy left hand, in thy glory.

It will not be as ye think, that I am to reign as a temporal king in Jerusalem, but all these things, that is, these which belong to My kingdom, are beyond your understanding; for to sit on My right hand is so great a thing that it surpasses the Angelic orders.

But by the cup and baptism, He means the cross; the cup, that is, as being a potion by Him sweetly received, but baptism as the cause of the cleansing of our sins. And they answer Him, without understanding what He had said; wherefore it goes on: And they said unto him, We can; for they thought that He spoke of a visible cup, and of the baptism of which the Jews made use, that is, the washings before their meals.
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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