Some scholars speculate that John had been imprisoned close to six months at this time. The reason for John's imprisonment is recorded in Mark 6:17-20. John was privileged enough as a prisoner to be able to communicate with his disciples.
John's question in Matthew 11:3 is puzzling to many, and there are several ideas regarding the reason why John made this inquiry. It is natural to wonder why John, who proclaimed Jesus as "the Lamb of God who takes away the sin of the world" (John 1:29), would have doubts concerning Jesus as "the Coming One". Some believe that John did not personally have doubts but merely wanted his disciples to ask Jesus this question in order to strengthen their faith. Others believe that John merely wanted to get Jesus to publicly declare Himself. However, in spite of these interesting explanations, it seems clear to me that John's faith did in fact waver. He was a prophet, but this did not mean that his inspiration would be to the level of omniscience or that it would remove all doubt from his mind. After all, Moses talked with God, and he had doubts (Exo. 3,4). Peter witnessed the transfiguration of Jesus and heard the voice of the Father (Matt. 17:1-9), yet he later denied the Lord with cursing (Matt. 26:69-75). Why is it that no one finds Peter's actions to be unbelievable, yet many have difficulty with the concept of John the baptizer doubting?
It is likely that John's faith was tested to the extent that Peter's was. John had faithfully executed his God-given role, but his expectations had not been fulfilled. The unfruitful trees had not been cut down, the grain had not been winnowed nor the chaff burned, and he could not see any progress toward these results (cf. Matt. 3:10-12). With nothing much to do except think, it is understandable how John's confinement in prison could lead to doubt, even though he had at one time plainly declared Christ to be the Son of God (cf. John 1:15,34).
The wording of John's question should also be noted - "Are you the Coming One, or do we look for another?" Certainly John, like all of the other Jews, had the idea that the Messiah would establish a physical, earthly kingdom and that He would reign as king on David's throne in Jerusalem. Since John couldn't see Jesus fulfilling this type of role, is it not possible that he wondered if Jesus was a forerunner like himself? Is it not possible that John, in his confusion, was beginning to think that Jesus would merely prepare the way for the ultimate Messiah? Let it be noted that regardless of why John asked this question regarding Jesus' identity, he should be credited with having enough confidence in Jesus to direct the question to Him.
When John the baptizer was asked if He was "the Christ", he plainly said, "No" (John 1:20,21). John probably hoped that Jesus would answer him just as plainly. However, Jesus chose to answer John's question indirectly as is seen in Matthew 11:4-6.
Jesus wanted John to be told of the things that He was saying and doing (cf. Luke 7:21). Informing John of these six things would remind him of Isaiah's prophecies regarding the Messiah (cf. Isa. 29:18; 35:5,6; 42:7; 61:1-3). John would understand Jesus to be saying, "My works speak for themselves. Since I'm doing the works characteristic of the Messiah, then certainly I am the Messiah!"
Probably the biggest reason, besides envy, as to why the Jewish religious leaders were offended by Jesus was because He didn't live up to their expectations concerning the Messiah. It appears that John the baptizer was in danger of falling into the same error. Thus, Jesus warned John - "Blessed is he who is not offended because of Me." Jesus was everything the Scriptures predicted the Messiah would be. However, He was not everything the people expected. Some lost faith in Him as a result.
We will continue studying Matthew 11 tomorrow.