I get asked this question a lot and thought others would find my answer helpful. Not that I claim to have discovered this myself but reading and gleaning has brought me to this conclusion.

In Luke 7:19-28, John the Baptist was in prison and sent two of his disciples to Galilee to ask Jesus a question.

And John, calling to him two of his disciples, sent them to the Lord, saying, Are you he who is to come, or shall we look for another?” And when the men had come to him, they said, “John the Baptist has sent us to you, saying, ‘Are you he who is to come, or shall we look for another?’ 

Some say John was doubting. Was Jesus really the one sent from God, the Messiah, or not?

Had John lost his faith? Of course, we cannot deny that this is a possibility. Of course John was in prison and things had not gone the way he may have hoped. If Jesus was the “sent one” why was he, John, languishing in the Machaerus Fortress?

Human weakness could possibly be an explanation though John the Baptist does not strike me as one who is going to doubt Jesus as the Messiah considering all that he had witnessed and known.

I think a better explanation might be that John the Baptist had to decrease and Jesus had to increase (John 3:30). What is the best way to get your disciples to leave you and follow the Messiah than to send them to Jesus to ask him if he is the Messiah?

In other words I don’t think it was doubt that caused John to send his disciples to ask Jesus that question. It was that he wanted to wean them off of himself so that they would realize who Jesus really was and begin to follow him.

Luke continues,

In that hour [Jesus] cured many of diseases and plagues and evil spirits, and on many that were blind he bestowed sight. And he answered them, “Go and tell John what you have seen and heard: the blind receive their sight, the lame walk, lepers are cleansed, and the deaf hear, the dead are raised up, the poor have good news preached to them.  And blessed is he who takes no offense at me.” (Luke 7:18-28)

Seeing Jesus’ miracles and their correspondence side-by-side with the prophecies of Isaiah certainly gave the proof to an honest heart and mind.

John, knowing his disciples had been prepared for the coming Messiah through his own preaching, knew they would recognize and follow him after their journey. He must decrease, Jesus must increase.

This seems to me an adequate and substantial explanation of John the Baptist’s question. I think St. Francis de Sales explained it this way and if anyone knows where the citation is, please let me know.

“The glorious St. John the Baptist did not send his disciples to Jesus our Lord to find out whether or not He was the Messiah. He had three reasons: first, to make Him known to the whole world. Second, he wanted to draw disciples only to his Teacher, to whose school he now sends them to be instructed personally by Him. Third, to detach them from himself and let them see Jesus so that they might come to Him in a manner worthy of Him. Therefore, John sent them to this Divine Majesty.”

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