When John the Baptist was imprisoned for preaching [Matt 14:3] he sent two of his disciples to ask Jesus a question and Jesus used this opportunity to tell his disciples about John. In this passage we see John the Baptist’s:

1. Doubt 11:2-6

   After getting thrown into prison, John began to doubt whether Jesus was the Messiah. After all, the Messiah was the King and surely servants of the king shouldn’t be thrown into jail. John had known to look for "that’ prophet about whom Moses prophesied [Deut 18:15-18; Jn 6:14] and that Jesus was that prophet and, therefore, the Messiah [Jn 1:32-34]. Nonetheless, a little time in jail caused him to doubt.

   To dispel his doubt, Jesus sent word back concerning all of his miracles. These would remind John of the miracles that were prophesied in Is 35:5-6, in the context of the coming Messiah [Is 35:3-4]. These would definitely bring comfort to a Jew. He also exhorted the disciples of John to encourage him not to be offended in Jesus [like Matt 13:57]. After all, it would have been very easy for John to be offended. He’d have to be thinking, "If you can heal the blind, why can’t you free the captives [Is 61:1]?"

2. Greatness 11:7-12

   Except for Jesus, John the Baptist was the greatest in the Kingdom of Heaven. People went out into the wilderness to see him because that’s where he was preaching [Matt 3:1]. They didn’t see a reed shaken with the wind, which would have indicated that John was just a fly by night preacher following a whim [like Eph 4:14]. No, John was so powerful that Herod feared him [Mk 6:18-20]. And he didn’t wear soft clothing like a Pharisee [Mk 1:6].

   He was a prophet and the people counted him as a prophet [Matt 14:5]. As a matter of fact he was the Lord’s messenger [Mal 3:1]. And there was none greater among them that are born of women because he was filled with the Holy Ghost from his mother’s womb [Lk 1:15].

   Yet he that is least in the kingdom of heaven will be greater than John because he will be living during the time when Is 9:6-7; Is 11; Heb 8, and Rom 11:25-26 are all fulfilled. He will be greater because he will have absolute assurance that his King is King of Kings. All in the kingdom of heaven will know him from the least to the greatest and have the law written in their hearts and minds while their king is ruling before their eyes. John didn’t get to see his king rule and had to die in prison, [the kingdom of heaven suffereth violence - Herod killed babies trying to kill Jesus, John got beheaded, and Jesus was arrested and crucified]. But when Jesus rules, violence in the kingdom is gone.

3. Importance 11:13-15
   
   If the Jews had accepted John’s preaching of the kingdom of heaven, he would have fulfilled the prophecy concerning the necessity of Elijah to come before the Lord sets up his throne in the earth [Mal 4:5]. The law and the prophets had prophesied until John [Lk 16:16], but now grace and truth had come by Jesus [Jn 1:17]. So, John ministered in the capacity of Elijah as the transitional figure to take the Jews from the Old Testament to their Messiah [Matt 17:10-13; Lk 1:17, although he was not actually Elijah, Jn 1:21]. However, since the Jews rejected their Messiah, Elijah will still have to come before the Second Advent [Matt 17:1-5; Rev 11 — he’s one of the two witnesses].