John the baptist, having baptized Christ already in Matthew 3:14 and having heard the voice from heaven that Christ was the son of God (Matthew 3:17), why did he send his disciples to Jesus to inquire of his Messiahship (Matthew 11:3)?
ESV - 3 And said to him, "Are you the one who is to come, or shall we look for another?
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Although John was chosen by God to announce the Kingdom and the coming Messiah, he probably had the same expectations as everyone else thinking Christ would presently set up his earthly kingdom, delivering Israel from Roman oppression. Although a tremendous man of faith and mightily used of God, just imagine spending most of your adult life eating grasshoppers, enduring the hardship of wilderness living, experiencing the persecution as a vessel set aside for God's glory then end up in jail. When questioned one time concerning his position to Christ, he stated in John 3:30 "He must increase, but I must decrease." However, John probably wasn't expecting it to turn out quite like this. I do not see any recorded evidence where Jesus ever visited John in prison. I would imagine his faith was really put to the test. The Lord himself gave John quite an endorsement in Matthew 11:10-11 " For this is he, of whom it is written, Behold, I send my messenger before thy face, which shall prepare thy way before thee. Verily I say unto you, Among them that are born of women there hath not risen a greater than John the Baptist: notwithstanding he that is least in the kingdom of heaven is greater than he." Even the greatest men of God have moments and periods of doubt. 2 Timothy 2:13 " If we believe not, yet he abideth faithful: he cannot deny himself."
John the Baptist, when he was conceived in his mother’s womb, was filled with the Holy Spirit (Luke 1:15). He was stirred in the spirit when he heard the salutation of Mary the mother of Jesus (Luke 1:41). Time in the wilderness and knowing the word of God prepared John for the Lord's coming for the people to repent and to be baptized for he said, "I am the voice of one crying in the wilderness" (Mat 3:3, John 1:23). When the time came for the Lord to be baptized he discerned in the spirit and recognized Jesus as the chosen one of God, and he witnessed the Spirit of the Lord descending upon him as a dove. Also, he heard a voice from heaven speaking, "This is my beloved son in whom I am well pleased." After preaching to the crowd, "This is the man that you have been waiting for and he has arrived," John now “was expecting for every mountain and hill to be made low and the crooked to be made straight and the rough to be made smooth” (Isaiah 40:4). Later he was imprisoned for his bold preaching of repentance to the high and low. In my opinion he was expecting the Lord to rescue him from the evil ones, and when it didn't happen he was probably in doubt about Jesus and then sent his disciples to inquire about his Messiaship. Many a times when our faith is not strong our unbelief brings doubts like in the book of Acts (see Acts 12:5). People who prayed without ceasing were in disbelief, for Peter was standing at the door. Elijah, who stopped the rain from falling, brought fire down from heaven, heard the voice of God, but later he was afraid when a messenger of Jezebel, Ahab's wife, confronted him (1 Kings 19:1). He ran into the wilderness and rested under a juniper tree and requested with the Lord that he might die (1 Kings 91:4) where the Lord spoke to him. John was born for a purpose to be fulfilled and then for Christ to come and proclaim the Kingdom of God.
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