Are you the one who is to come, or should we look for another?" -- Matthew 11:3
That is a strange question, especially coming from John the Baptist.
Why? Because a) John and Jesus were cousins; b) John exclaimed, "Behold, the Lamb of God, who takes away the sins of the world" when Jesus approached him to be baptized; c) John heard God the Father say, "This is my son of whom I am well pleased"; and d) John saw the Holy Spirit descend upon Jesus. So, it is very unlikely John was confused. The coming of Jesus was not happenstance for John - to announce the coming of the Messiah was his entire mission and calling; his raison d'être.
Rather than uncertainty, John knew he had little time left on death row. Some of John's disciples still thought he was the Messiah and some thought the Messiah was going to storm the capital and retake Jerusalem from the Romans (Jesus was certainly not living up to that billing). So it makes sense that before he died, he would want his disciples to know for themselves who Jesus was, and that hearing Jesus' responses first hand would be the best way to persuade them - far more than his own words.
This strategy is further supported by the question John put forth. He did not tell his disciples to ask if he was the "Messiah;" the question he gave them was, "Are you the one to come?"
John is basically teeing it up for Jesus and Jesus hits it out of the park. By responding, "the blind see, the deaf hear, lepers are cleansed, the dead raised, and the poor have good new proclaimed to them," Jesus is quoting 2 Kings 5, Zechariah 2, and Isaiah 26, 35, and 61. Most Jews in the first century knew their scripture and would know that Jesus' references were about the coming of the LORD (Yahweh), not the Messiah. Jesus' response meant that he was both God and Messiah. The Jews were not expecting that: they were expecting a Kingly Messiah, and a Priestly Messiah, and a Suffering Messiah (in fact, the Essenes were preparing for all three); but nobody expected that one person would be all three, let alone the LORD himself.
Jesus goes on to pay the highest compliments to John, calling him the greatest of all the Old Testament prophets, because he got the job of being the forerunner heralding the coming of God.
Jesus adds a strange statement in verse 6: "And blessed is he who takes no offense at me." What is he referring to?
By proclaiming that he was also God would raise the stakes in Israel manifold. Claiming one is God is a violation of the 1st commandment and blasphemy, subject to the death sentence.
In fact, the religious authorities indeed took great offense at this and was ultimately the reason Jesus was sentenced to death.
In the end, however, Jesus comes to Jerusalem willingly to lay down his life.
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