Matthew 11 begins with a difficult realization: Jesus was right in what He said in the Mission Discourse about persecution. By reporting that John is in prison, Matthew certainly wants the reader to understand that Jesus was correct, obedience in the mission of spreading the good news of the Kingdom will result in discomfort and persecution.
As if to address the question of whether Jesus is worth all this, Matthew shows an interaction between the messenger of John the Baptist and Jesus. Although we're not giving the internal thoughts and motivations of John, it seems clear enough from the text that the "deeds of the Christ" of raised some questions for John. At least it has raised the question of Jesus's identity.
“Are you the one who is to come, or shall we look for another?”
Thus the question of Jesus's identity is raised from the outset of the chapter. Who is this man and is He worth going to jail for? Is He worth dying for?
But Jesus answers the question in a surprising way. To John He simply says that John shouldn't diminish the significance of His deeds.
"The blind receive their sight and the lame walk, lepers are cleansed and the deaf hear, and the dead are raised up, and the poor have good news preached to them."
Jesus's deeds should be enough to identify him, even if He isn't exhibiting the traits of the Messiah that John was expecting (the "winnowing fork" and all that, see Matt. 3:12).
As John's messengers turn away to return to him, Jesus turns to the crowds and answer a very different question, "who is John?"
Who is this John? At this point the wisdom of Christ is on brilliant display, for in explaining to the crowd who John is, Jesus also answers the question of who HE is.
Here, Jesus shows Himself to be as shrewd as a serpent and as harmless as a dove. He can look straight-faced at the crowds around Himself and identify Himself as the divine Messiah. But only those with ears to hear can understand Him.
He identifies John as the messenger who would come in the spirit of Elijah to prepare the way of the Lord (Micah 3:1) before the great and awesome day of the Lord (Micah 4:5). John is Elijah, sent to prepare the way of the Lord. Jesus is in effect saying that John is Elijah and He Jesus is the Lord.
In a remarkable way, this portion of Matthew (11:2-19) reveals the wisdom of Christ. He can reveal His divine nature, but do it in a way that won't get Him killed before He is ready to lay down His life.
Just think about that for a moment. The creator of the universe has to be careful so as to not be rejected and killed by His creation.
Think about the monstrous effects of sin in the world and in our hearts. People would sooner reject their creator, turn on Him, and ultimately kill Him than they would accept what He says and follow Him. Creation would sooner put the Creator up on the cross than worship Him.
Think also of how this text makes much of Christ. Long after Christ's earthly ministry we have Matthew's own testimony, a testimony that elevates and lifts up Christ.
We also see how John elevates Christ. The words of Jesus that at fist seem to be about John turn out to reveal the divinity of Christ. Once again we see John doing his Job of elevating Jesus.
He loves to point to Jesus and make much of Him.
Remember John saying, “behold the lamb of God who takes away the sins of the world”?
In our own hearts, in our lives, in our families, and in our public testimonies, we need to make much of Christ.