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Matthew 11:2 When John, who was in prison, heard about the deeds of the Messiah, he sent his disciples 3to ask him, “Are you the one who is to come, or should we expect someone else?”

Was John's faith shaken while being imprisoned? Did he not know that there would be a second coming of Jesus?

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Did John experience a moment of lack of sufficient faith in Matthew 11:3?

Matthew 11:2 When John, who was in prison, heard about the deeds of the Messiah, he sent his disciples 3to ask him, “Are you the one who is to come, or should we expect someone else?

Was John's faith shaken while being imprisoned? Did he not know that there would be a second coming of Jesus?

No John did not experience lack of faith, since John saw God’s spirit descend upon Jesus and heard God’s voice of approval when baptizing Jesus. John’s question may cause some to conclude that his faith has grown weak. But this is not so. Jesus would not speak so highly of John, which he does on this occasion if John has begun to doubt. Why, then, does John ask this question?

The Jewish Messianic Expectation in the Time of Jesus.

https://www.livius.org/articles/religion/messiah/messiah-10-messianic-expectations/

Extract from the above.[ ]

[ To a certain extent, the answer is easy: the Messiah(s) would restore Israel. Adherents of the military messianology expected that the son of David would throw out the Romans and restore Israel politically; others believed that he would give the true interpretation of the law and inaugurate Israel's ethical revival; still, others hoped for cultic reforms and a cleaning of the temple by the true high-priest; and there must have been people who combined these expectations.]

Also, Jewish sources agree with Luke 2:38 that at the time were waiting for Jerusalem's deliverance from the hated Roman rule and would establish His reign of peace. They tried to make him an earthly king. (John 6:15) When he would not fulfill their expectations, they rejected him.

Luke 2:38 NASB

At that very moment, she came up and began giving thanks to God, and continued to speak of Him to all those who were looking for the redemption of Jerusalem.

Evidently the expectation that the Messiah would be an earthly king was shared by John the Baptizer and his disciples. John knew Jesus to be the Messiah and the Son of God, having seen him anointed with holy spirit and having heard God’s voice of approval. John did not lack faith. (Mt 11:11) So his question, “Are you the one who is to come, or should we expect someone else?” may have meant, ‘Are we to expect yet another one who will fulfill all the hopes of the Jews?’

Christ in reply pointed to the works he was doing (which things had been foretold in the Hebrew Scriptures). He concluded: “And happy is he who has not stumbled over me.” This answer, while implying that faith and discernment would be needed, would satisfy and comfort John, assuring him that Jesus was the One who would fulfill God’s promises.

Luke 7:18-23 NASB

A Deputation from John

18 The disciples of John reported to him about all these things. 19 Summoning [a]two of his disciples, John sent them to the Lord, saying, “Are You the [b]Expected One, or do we look for someone else?” 20 When the men came to Him, they said, “John the Baptist has sent us to You, to ask, ‘Are You the [c]Expected One, or do we look for someone else?’” 21 At that [d]very time He cured many people of diseases and afflictions and evil spirits; and He gave sight to many who were blind. 22 And He answered and said to them, “Go and report to John what you have seen and heard: the blind receive sight, the lame walk, the lepers are cleansed, and the deaf hear, the dead are raised up, the poor have the gospel preached to them. 23 Blessed is he [e]who does not take offense at Me.”

Also, prior to his ascension, Jesus’ disciples held the view that he would at that time deliver Israel from Roman domination and set up the Kingdom that is to restore the reign of the Davidic line on earth

Luke 24:21 NASB

21 But we were hoping that it was He who was going to redeem Israel. Indeed, besides all this, it is the third day since these things happened.

Acts 1:6 NASB

6 So when they had come together, they were asking Him, saying, “Lord, is it at this time You are restoring the kingdom to Israel?”

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It doesn't seem to be a loss of "faith" - as in "is Jesus the Messiah" - rather it is confusion over unmet expectations of what is supposed to happen when the Messiah arrives.

Many in Jesus' day - particularly the Essenes (Dead Sea Scrolls) - saw the cosmos and God's plan as having the "current age" and the "age to come" where God would unleash his judgment immediately. It appears that John assumed that once the Messiah was inaugurated that the eschatological battle would ensue.

John says, "The ax is already at the root of the trees, and every tree that does not produce good fruit will be cut down and thrown into the fire." (Matt. 3:10)

and Matt. 3:12:

His winnowing fork is in his hand, and he will clear his threshing floor, gathering his wheat into the barn and burning up the chaff with unquenchable fire.”

John seems to be wondering, if Jesus is the Messiah, then why he is still in jail?

Notice that when Jesus talks to the crowd about John in Matt. 11 he references a number of passages in Isaiah that have to do with the coming Messiah. Note John's question, "Are you the one who is to come" compared to Isaiah 35.

Isaiah 35:4-6 reads:

say to those with fearful hearts, “Be strong, do not fear; your God will come, he will come with vengeance; with divine retribution, he will come to save you.” Then will the eyes of the blind be opened and the ears of the deaf unstopped. Then will the lame leap like a deer, and the mute tongue shout for joy.

Additionally, Isaiah has numerous references to the captives being set free!

Isaiah 42:7 says:

to open eyes that are blind, to free captives from prison, and to release from the dungeon those who sit in darkness.

Finally, Isaiah 61:1:

The Spirit of the Sovereign Lord is on me, because the Lord has anointed me to proclaim good news to the poor. He has sent me to bind up the brokenhearted, to proclaim freedom for the captives and release from darkness for the prisoners,

Unfortunately, Jesus did not show up to lead the cosmic battle in the manner that many had expected. His method of combating evil forces was "forgiveness" and going to the cross.

Jesus even tells the parable of the Weeds (or Tares) in Matt. 13:24-30. In this parable, he says, essentially, "leave the weeds there and they will be dealt with at harvest." This is not what many expected.

Jesus' comment to John about "not stumble" (Matt. 11:6) is a way of encouraging John that although it may look different than he expected, the age of the Messiah is here.

It seems we may liken this to many Christians who adopt a particular framework for the end-times. And then, when it doesn't happen as they expected, they become dejected. For instance, see the "Great Disappointment of 1844."

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