Matthew 11:2

Now when John heard in the prison the works of Christ, he sent two of his disciples

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WEBBE

Now when John heard in the prison the works of Christ, he sent two of his disciples

BSB

Meanwhile John heard in prison about the works of Christ, and he sent his disciples

KJV

Now when John had heard in the prison the works of Christ, he sent two of his disciples,

ASV

Now when John heard in the prison the works of the Christ, he sent by his disciples

BBE

Now when John had news in prison of the works of the Christ, he sent his disciples

Original Greek

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The early church

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John then is providing not for his own, but his disciples' ignorance; that they might know that it was no other whom he had proclaimed, he sent them to see His works, that the works might establish what John had spoken; and that they should not look for any other Christ, than Him to whom His works had borne testimony.
Hilary of Poitiers · d. 367Catena Aurea (Aquinas, 1274)
In these things which were done concerning John, there is a deep store of mystic meaning. The very condition and circumstances of a prophet are themselves a prophecy. John signifies the Law; for the Law proclaimed Christ, preaching remission of sins, and giving promise of the kingdom of heaven. Also when the Law was on the point of expiring, (having been, through the sins of the people, which hindered them from understanding what it spake of Christ, as it were shut up in bonds and in prison,) it sends men to the contemplation of the Gospel, that unbelief might see the truth of its words established by deeds.
Hilary of Poitiers · d. 367Catena Aurea (Aquinas, 1274)
(in Luc. 7. 19.) And perhaps the two disciples sent are the two people; those of the Jews, and those of the Gentiles who believed.
Ambrose of Milan · d. 397Catena Aurea (Aquinas, 1274)
But what follows is completely among the controverted points. Of what nature then is this? Their saying, "Art Thou He that should come, or do we look for another?" That is, he that knew Him before His miracles, he that had learned it of the Spirit, he who had heard it of the Father, he who had proclaimed Him before all men; doth he now send to learn of Him, whether it be Himself or no? And if yet thou didst not know that it is surely He, how thinkest thou thyself credible, affirming as thou dost concerning things, whereof thou art ignorant? For he that is to bear witness to others, must be first worthy of credit himself. Didst thou not say, "I am not meet to loose the latchet of His shoe?" Didst thou not say, "I knew Him not, but He that sent me to baptize with water, the same said unto me, Upon whom thou shalt see the Spirit descending and resting upon Him, the same is He which baptizeth with the Holy Ghost?" Didst thou not see the Spirit in form of a dove? didst thou not hear the voice? Didst thou not utterly forbid Him, saying, "I have need to be baptized of Thee?" Didst thou not say even to thy disciples, "He must increase, I must decrease?" Didst thou not teach all the people, that "He should baptize them with the Holy Ghost and with fire?" and that He "is the Lamb of God that taketh away the sin of the world?" Didst thou not before His signs and miracles proclaim all these things? How then now, when He hath been made manifest to all, and the fame of Him hath gone out everywhere, and dead men have been raised, and devils driven away, and a display made of so great miracles, dost thou after this send to learn of Him? What then is the fact? Were all these sayings a kind of fraud: a stage play and fables? Nay, who that hath any understanding would say so? I say not, John, who leaped in the womb, who before his own birth proclaimed Him, the citizen of the wilderness, the exhibitor of the conversation of angels; but even though he were one of the common sort, and of them that are utterly outcast, he would not have hesitated, after so many testimonies, both on his own part and on the part of others. Whence it is evident, that neither did he send as being himself in doubt, nor did he ask in ignorance. Since no one surely could say this, that though he knew it fully, yet on account of his prison he was become rather timid: for neither was he looking to be delivered therefrom, nor if he did look for it, would he have betrayed his duty to God, armed as he was against various kinds of death. For unless he had been prepared for this, he would not have evinced so great courage towards a whole people, practised in shedding blood of prophets; nor would he have rebuked that savage tyrant with so much boldness in the midst of the city and the forum, severely chiding him, as though he were a little child, in hearing of all men. And even if he were grown more timid, how was he not ashamed before his own disciples, in whose presence he had so often borne witness unto Him, but asked his question by them, which he should have done by others? And yet surely he knew full well, that they too were jealous of Christ, and desired to find some handle against Him. And how could he but be abashed before the Jewish people, in whose presence he had proclaimed such high things? Or what advantage accrued to him thereby, towards deliverance from his bonds? For not for Christ's sake had he been cast into prison, nor for having proclaimed His power, but for his own rebuke touching the unlawful marriage.
John Chrysostom · d. 407Homilies on Matthew
For what intent then did he send to ask? John's disciples were starting aside from Jesus, and this surely any one may see, and they had always a jealous feeling towards Him. And it is plain, from what they said to their master: "He that was with thee," it is said, "beyond Jordan, to whom thou barest witness, behold, the same baptizeth, and all men come unto Him." And again, "There arose a question between John's disciples and the Jews about purifying." And again they came unto Him, and said, "Why do we and the Pharisees fast oft, but Thy disciples fast not?" For as yet they knew not who Christ was, but imagining Jesus to be a mere man, but John greater than after the manner of man, were vexed at seeing the former held in estimation, but the latter, as he had said, now ceasing. And this hindered them from coming unto Him, their jealousy quite blocking up the access. Now so long as John was with them, he was exhorting them continually and instructing them, and not even so did he persuade them; but when he was now on the point of dying, he uses the more diligence: fearing as he did lest he might leave a foundation for bad doctrine, and they continue broken off from Christ. For as he was diligent even at first to bring to Christ all that pertained to himself; so on his failing to persuade them, now towards his end he does but exert the more zeal. Now if he had said, "Go ye away unto Him, He is better than I," he would not have persuaded them, minded as they were not easily to be separated from him, but rather he would have been thought to say it out of modesty, and they would have been the more rivetted to him; or if he had held his peace, then again nothing was gained. What then doth he? He waits to hear from them that Christ is working miracles, and not even so doth he admonish them, nor doth he send all, but some two (whom he perhaps knew to be more teachable than the rest); that the inquiry might be made without suspicion, in order that from His acts they might learn the difference between Jesus and himself. And he saith, Go ye, and say, "Art thou He that should come, or do we look for another?"
John Chrysostom · d. 407Homilies on Matthew

Commentary

Matthew Henry · Verses 2–6

Some think that John sent this inquiry for his own satisfaction. Where there is true faith, yet there may be a mixture of unbelief. The remaining unbelief of good men may sometimes, in an hour of temptation; call in question the most important truths. But we hope that John's faith did not fail in this matter, and that he only desired to have it strengthened and confirmed. Others think that John sent his disciples to Christ for their satisfaction. Christ points them to what they heard and saw. Christ's gracious condescensions and compassions to the poor, show that it was he that should bring to the world the tender mercies of our God. Those things which men see and hear, if compared with the Scriptures, direct in what way salvation is to be found. It is difficult to conquer prejudices, and dangerous not to conquer them; but those who believe in Christ, their faith will be found so much the more to praise, and honour, and glory.

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Cross-references: Treasury of Scripture Knowledge. Hebrew and Greek data from STEPBible.org (Tyndale House, Cambridge), CC BY 4.0. Library: sources.