Matthew 11

2 John the Baptist was put in prison earlier (Mat 4:12, Mark 6:17-18).
3 John had proclaimed Jesus as the Messiah when he baptized Him. Perhaps after his lengthy stay in prison, he began to harbor doubts, although God had revealed Jesus' identity to him earlier. John had predicted that Jesus would bring judgement on the world and bring about dramatic political and social reform (Mat 3:7-12). John was focusing on his immediate circumstances and did not understand that Jesus' method of reformation was much different than he anticipated, and judgement would occur much later in time.
4 Jesus does not chastise John, nor does He set out to set John free. Instead, Jesus gives John's disciples a word to encourage his faith.
5 Jesus often relies on the miracles He performed to serve as evidence of His divine origin and authority as the Messiah. Miracles, however, are not enough to convince people. In addition, people must hear, understand, and accept the Good News that God loved them and would forgive their sins through the sacrifice of the Messiah, Jesus.
6 Despite the miracles and preaching, most people would never see Jesus as more than a man. They might see the lives of some people radically change, but the world will continue to be dominated by sin until Judgement Day. Since the salvation work of God is usually invisible, subtle, and "slow," people can make the mistake of thinking that He is not working at all (or even worse, they may think He does not exist at all). To these people, the message of Jesus is offensive. They might consider Him a failure or a fraud. Those who do know Jesus have the evidence of the past and the hope for the future that is a great blessing in this lifetime and the next.
7 Jesus' intent was to remind the people that John was not a man carried about by external whims, nor was he an undecided man. He had a definite mission from God and he had followed it through wholeheartedly. People had gone to see him because he was a prophet without compromise.
8 Here Jesus appears to contrast John with political activists. Those who want to have political influence tend to stay close to those in command and dress appropriately. Instead, John was on a mission from God. His purpose was to lay the foundation for the spiritual revolution that would occur when Jesus began His ministry. Instead of dressing to impress people, he dressed in clothing reminiscent of the prophet Elijah. Instead of words of political savvy, he spoke the powerful words of God.
9 There was no doubt that John was a prophet, but he was a special prophet because he had the role of forerunner to the Messiah.
10 Isa 40:1-5 speaks of the watchman that announces the immediate approach of God.
11 John was the last of the Old Testament prophets and was, in fact, the greatest among them because of his special assignment. He announced the coming of the Messiah, but for unknown reasons did not participate in Jesus' ministry. Does this mean that John will be excluded from heaven? Probably not, but John apparently missed the most important aspect of heaven -- a relationship with Jesus. Our entrance into heaven will not depend on our lineage or works, but rather on our relationship with Jesus (Mat 7:21-23). John announced Jesus as the Messiah, but choose to remain aloof from Him and continued his own ministry and had his own disciples. If he had chosen to give up his own ministry and follow Jesus; he would have had the joy of tasting the new covenant as well as the old. As it is, those who had a faith relationship with Jesus for even a short period will have a greater reward in heaven than John the Baptist will.
12 The world's reaction to the word of God is often hostile. They generally like the idea of God's love, but will not tolerate the pronouncement of God's judgements. Confronting people with sin can make them feel uncomfortable and threatened. These feelings are compounded when people are "forced" to behave in a godly manner when they do not recognize His authority over them. They attack the messenger of God because they can not attack God Himself, or they may not believe that God exists. "Taking the kingdom by force," probably refers to the idea of seizing control of believers to contain or kill them.
13 The prophecies referred to here are the prophecies of the Messiah's first appearance. There would no longer be any prophecies like this because they were fulfilled in Jesus. There are prophesies about His second coming, but God has made them intentionally vague so that we will not find out when exactly that will be (Mat 24-25:13, Rev).
14 Mal 4:5 indicates that Elijah would appear before the Messiah came. John denied being Elijah (John 1:21), but Jesus indicates that he fulfilled the role, even if he did not understand it.
15 The idea is that if one thinks about these things, they will make sense.
17 The children of the parable were never satisfied with the games they were playing. In one group did not want to play the same game as the other group they did nothing except complain.
18 John lived an aesthetic life. The people who did not like his message used his self-depriving lifestyle as an excuse not to listen to him.
19 On the other hand, Jesus did not deprive Himself of food or drink. He ministered to outcasts, which means He became a friend with those who "religious" people shunned. Those who did not like the message of Jesus used both His normal and loving characteristics against Him as an excuse not to listen to Him. Thus, like the children in the parable there was nothing that would satisfy them.

The dissatisfied people could not see that John was living a lifestyle of a prophet. His concern was for the word of God, so he was not so concerned about his food and clothing. Jesus was the Messiah, and His ministry was to save people from their sins. Often, it is easier to see fruit from a message of repentance to those who already know they are sinners. Relationships are important in ministry, and a good relationship with God is the key to salvation.