Are we to understand that somehow John was disappointed in Jesus? Was John offended at the way Jesus was conducting His ministry? Were these words of “takes no offense” directed at John? While all of that is possible, because we don’t really have a basis upon which to determine John’s mindset as he sat in prison, the likely answer is no. Considering the context of the words that He spoke, and the fact that His experience in Nazareth (at least according to a comparative chronology) would have come before this question from John, along with the record of Jesus going on to offer high praise and honor to John in the following verse, it is far more reasonable to presume that it is the Nazareth incident that Jesus would have in mind when He provided His answer to John and said “Blessed is anyone who takes no offense at Me.”
Though Matthew’s story makes no reference to the attempted murder of Jesus in Nazareth as reported by Luke, because Jesus’ response to John’s disciples in Matthew contains words quite similar to those that provoked the harsh response in Luke, because the people of Nazareth certainly took offense to Jesus’ words, and even though we treat the Gospel stories differently because they have different purposes (the separate stories of John’s disciples and Jesus’ Nazareth experience are isolated to Matthew and Luke) and don’t necessarily rely on one to make sense of the other, making the connection that Jesus may have been thinking of Nazareth as He spoke the words of “take no offense” seems to be a reasonable step.
Not only did Jesus insist that a state of blessing arises from not being offended at Him (Matthew 11:6), He makes it equally clear, through the pronouncement of the terms of His ministry, that apart from dashing certain messianic expectations, there was truly no reason to take offense. Unless, that is, somebody wants to take offense to the way that Jesus went about the business of His work of causing the blind to see, the lame to walk, lepers to be cleansed, the deaf to hear, the dead to be raised, and the poor to have the good news of the breaking in of God’s kingdom preached to them. Jesus was not thundering down from on high, condemning people according to His checklist of “sins of the flesh,” or setting Himself up as the ruler and arbiter of the people in an attempt to exercise an overt control over their lives and actions. He flatly rejected any and all attempts of the people to force Him into this position. Of course, there were those that did take offense (especially the Temple authorities), but we can be reasonably certain that John the Baptist was not one of them, as “Jesus began to speak to the crowd about John” (Matthew 11:7), doing so in a very positive manner.
After John disciples had gone away, presumably to return to John with Jesus’ response in confirmation of his inquiry, Jesus says, “What did you go out to see? A prophet?” (11:9a). Here, Jesus honors John the Baptist by classing him with the prophets of old, those who did so much to call the leaders of the people to account, adding “Yes, I tell you, and more than a prophet” (11:9b). More than a prophet? Yes, “This is the one about whom it is written: ‘Look, I am sending My messenger ahead of You, who will prepare Your way before You’.” (11:10) With these words, Jesus has continued the subtle reinforcement of His statements about Himself that can be taken to confirm His status as Messiah. Here, He quotes from Malachi.
Looking to the prophectic work, we find those words followed with, “Indeed, the Lord you are seeking will suddenly come to His temple, and the messenger of the covenant, whom you long for, is certainly coming” (3:1b). These words from Malachi, in Jesus’ time (and certainly at the time of the composition of Matthew), were taken to be a clear reference to one who would precede the messiah, as well as to God’s messiah Himself. So Jesus, in assigning this accepted role of “messenger” to John (with this concept of the one to come and the one preceding him reinforced elsewhere in the Gospels---the “who do you say that I am” question and its attendant responses), has continued to indirectly declare His own Messiah-ship. He further reinforces this claim about John (and therefore also about Himself) by adding “And if you are willing to accept it, he is Elijah, who is to come” (11:14). Clearly, Jesus takes no issue with John at all, and gives no negative thoughts to his inquiry, as He will also say, “among those born of women, no one has arisen greater than John the Baptist” (11:11a).