When politicians are imprisoned for the right cause their popularity grows with them. They come in as a prisoner but come out as a hero. They longer they stay in jail the bigger support they receive on the day of their release. This principle does not apply for prisoners imprisoned in the name of the Lord. Being arrested and imprisonment their popularity is dwindles and eventually dies. Their followers live in fear and run away and hide. The date of their being released was unknown and in most cases their fate had already been decided. The judgment was only the formality and the execution was only a matter of when.
John, now in prison was able to know the movements of the expected coming of the Messiah through the information of his disciples. John would like personally to introduce Jesus to his disciples the one whom John had been preparing the way for his coming but John could not. He sent a delegation to meet Jesus for clarification of his query. What John was concerned most about was the news of the Messiah whether he was the right one or someone else? The news was particularly important for John because when the Messiah is coming John knows that his mission has come to its completion. John's delegation came to see Jesus with one single question.
Are you the one who is to come or have we got to wait for someone else?
Jesus confirmed not of his identity but told John's disciples about his works. Prophet Isaiah had prophesised that the Messiah will open the eyes and the ears of the deaf. The lame shall walk free and the tongues loosened (Is 35,4-6). Jesus has done all what the prophet had foretold and he has done much more than what has been expected.
John's disciples returned confirming to John of what he had heard about Jesus. In the mean time Jesus praised John for his excellent works. Any person that Jesus praised would receive great reward and as we knew that John had received the great reward which was to enter God's kingdom, not long after Jesus praised him.
The road to glory for a politician is the day when they are released from prison while the road to glory for being faithful to God is the day when they are crowned with God's glory and the greatest glory happened after one has shed his own life and blood.
Another reason that John would like to confirm that Jesus is the Messiah is that John would like to introduce his own disciples for Jesus who would open their minds and hearts to Jesus' preaching and hopefully some of them would become the disciples of Jesus. If that was the case then John would prepare not only the way for the Lord but he also prepared the pool of his own disciples for the Lord to choose from