Immediately after Jesus raised up the dead son of the widow of Nain, the people began spreading the news throughout all the regions of Galilee and into Judea that a great Prophet had arisen among them. The sense of this remark is that they referred to the Prophet whom Moses predicted would come (Deuteronomy 18:15). This Prophet would be similar to Moses in that he would show the Jews how they must behave. He would be a Second Moses; the Targum Jonathan calls him the Second Deliverer at Deuteronomy 18:15. His coming implied Moses (i.e. the Law) was not enough. Either changes had to be made or a deeper meaning had to be revealed. Moreover, if anyone didn’t listen and obey this Deliverer, God, himself, would call that person into account (Deuteronomy 18:18-19). What is interesting at this point is who began to doubt Jesus.
A problem arose when stories of unexpected things Jesus was doing were brought back (Luke 7:18). Jesus didn’t preach and act as John and others had anticipated the Messiah doing. John was willing to die in prison, but he didn’t expect to die there. He saw Jesus as a great warrior-deliverer who would gather Israel together and defeat Israel’s enemies. He expected Jesus to take over the reins of government and rule as David’s long awaited Son. Instead, Jesus was teaching folks to love your enemies and bless them who curse you (Luke 6:27-28). On the surface it seemed Jesus was making John’s ministry into a sham. John had told his disciples that Jesus was the expected Messiah (John 1:30), and he would bring judgment upon evil doers (cf. Luke 3:16-17)? The simple truth is John was speechless. He was embarrassed with Jesus behavior. It was so unlike what he expected and even preached would occur.
Imagine, the predicted Messiah healed the Roman centurion’s servant, who also happened to be the son of a person of rank in Herod’s household—the very one who had imprisoned John (Luke 7:2-10; John 4:45-54). It looked more like the Messiah was siding with the enemy, than fulfilling the hopes of Israel! Add to this the fact that Jesus and his disciples didn’t seem to fast (Luke 5:33), and cleanliness issues didn’t seem to matter to Jesus (Luke 5:30; 7:14). Had he come to destroy the Law (Matthew 5:17)? What was John to think?
So, John sent two of his disciple to Jesus to ask, if he truly was the expected Messiah (Luke 7:19-20). Jesus replied to John’s query with gentleness but also with firmness. He told John’s disciples to return to John and report what they saw and heard. Moreover, Jesus explained to them what to say, because up to this point they reported to John only what they saw and heard as that pertained to what was expected of Jesus by all Jews who looked for the coming of the Messiah. Jesus pointed out “…the blind see, the lame walk, the lepers are cleansed, the deaf hear, the dead are raised, and the gospel is preached to the poor” (Luke 7:21-22). These are all Messianic works the expected Messiah was predicted to do when he came (cf. Isaiah 29:18-19; 32:3-4; 35:5-6). This was Jesus’ gentle reply.
God refuses to allow men to compartmentalize his behavior, which they try to do so they could predict precisely what to expect of God. This sort of thing presuppose men already know God, and it doesn’t leave one’s heart open to learn from him. Learning becomes a problem when people think they already know, and this usually occurs when a particular truth is overemphasized. John was in prison and depended on accurate reports about Jesus from his disciples. The problem is they reported slanted information (cf. John 3:26), and John had to base his perception of Jesus on such reports. Therefore, he sent two of his disciples to acquire specific information according to the question he asked of Jesus.
Jesus’ firm reply to John came as a blessing with an implied warning. He said, “blessed is he who is not offended in me.” (Luke 7:23). The Greek word is skandalizo (G4642), meaning to offend or take offense. The word scandalize comes from this word. John at the very least took offense with Jesus’ ministry (as he understood it from the slanted reports he received from his disciples), and could have even been scandalized by it. After all, John predicted Jesus would judge wrong behavior with fire, meaning swift and final judgment. While Jesus does judge wrong behavior, it is not in the manner in which John (nor other Jews) expected.
John’s comfort came by Jesus telling him that he didn’t err by pointing to Jesus as the coming Messiah, and he was able to understand that the Messianic works Jesus was doing could only be fulfilled in the ministry of the Messiah (cf. John 3:27). The fact that Jesus had to specifically tell the two disciples John sent what exactly to report back to John, implies John wasn’t receiving this kind of information when his disciples described Jesus’ ministry. In other words, Jesus was telling John that he may not fully understand at present why Jesus behaved as he did, but afterwards he would understand (cf. John 13:7).