Charles Ellicott Commentary Matthew 11:2

"Now when John heard in the prison the works of the Christ, he sent by his disciples" — Matthew 11:2 (ASV)

When John had heard in the prison — John's situation in prison was, to a large extent, that of a prisoner treated with respect. Herod himself paid attention to him and gladly listened to him. Herodias had not yet found an opportunity for revenge. His disciples came and went freely. We have already seen some of these disciples present when our Lord was teaching (Matthew 9:14), and they would certainly have heard of such wonders as those narrated in Matthew 8:9.

He himself, in the prison of Machaerus, was languishing with the sickness of hope deferred for the Messianic kingdom he had proclaimed. His disciples reported back what they had seen and heard (Luke 7:18), yet everything continued as before. There was no deliverance for him or for Israel. Under the influence of this disappointment, he sent two of his disciples with the question recorded in the next verse.