John wanted a clear answer about who Jesus is. "He that should come" means the promised One; Barnes explains the question as "Art thou the Messiah, or the Christ?" Commentators differ on whose doubt it was. Barnes admits, "It is not certainly known why John sent to Jesus": perhaps to satisfy his disciples, perhaps to confirm for himself. Gill holds that John did not doubt, and sent the question for his disciples' sake, "to remove all doubt and hesitation from them about Christ." Matthew Henry says, "The faith of John Baptist himself, or at least of his disciples, wanted to be confirmed." Either way, the question was honest, and it went straight to Jesus.

Jesus answered with works and a message. "In that same hour he cured many of their infirmities and plagues, and of evil spirits; and unto many that were blind he gave sight" (Luke 7:21). Then He said, "Go your way, and tell John what things ye have seen and heard; how that the blind see, the lame walk, the lepers are cleansed, the deaf hear, the dead are raised, to the poor the gospel is preached" (Luke 7:22). He added, "blessed is he, whosoever shall not be offended in me" (Luke 7:23). Barnes says of these miracles, "They were proof that he was the Messiah."

John was in prison because Herod the tetrarch had been "reproved by him for Herodias his brother Philip's wife" (Luke 3:19-20). Gill names the place as the castle of Machaerus. Earlier, the people had wondered whether John himself was the Christ, and he told them, "one mightier than I cometh" (Luke 3:15-16).

In the Greek, "he that should come" is ho erchomenos, literally "the coming one," a present participle. "Look we for" is prosdokaō, to look for or expect, in the present tense: are we still to keep waiting?

Jesus did not scold John for asking. He let the evidence speak and sent the messengers back with what they had seen. The list He gave echoes the words He read from "the prophet Esaias" at Nazareth: "to preach the gospel to the poor ... recovering of sight to the blind" (Luke 4:17-18). What John had heard about, Jesus was now doing.

Right after the messengers left, Jesus praised John publicly as "much more than a prophet" (Luke 7:24-28). An honest question did not lower John in Jesus' eyes. Jesus answered John's honest question in His own way.