After the Transfiguration, Jesus returns to the crowd and is met by a man with a demon possessed son (17:14-16). The father of a possessed son comes to Jesus and kneels before him, requesting that Jesus do what his disciples failed to do, heal his son. Matthew 17:17 responds by addressing a “faithless and twisted generation.”
Despite Jesus giving the disciples his authority over demons (Matthew 10:1), the remaining disciples could not cast out the demon (v. 16). Nolland suggests the disciples “failed to fulfill their Mt. 10 mandate” and they are repeating the pattern of the wilderness generation (Matthew, 710). In fact, Jesus seems to rebuke the disciples and the crowd: “O faithless and twisted generation, how long am I to be with you? How long am I to bear with you?” (17:17)
Jesus seems exasperated! He calls the crowd a “faithless and twisted generation” (Mark has only “faithless generation”) and wonders out loud how long he will have to put up with them! The “faithless generation” alludes to the wilderness generation. After the ten plagues and the miraculous rescue from Egypt through the Red Sea, the theophany at Mount Sinai, the Israelites still complained and doubted God’s power to give them the Promised Land.
Isaiah 63:8-10 (ESV) For he said, “Surely they are my people, children who will not deal falsely.” And he became their Savior. 9 In all their affliction he was afflicted, and the angel of his presence saved them; in his love and in his pity he redeemed them; he lifted them up and carried them all the days of old. 10 But they rebelled and grieved his Holy Spirit; therefore he turned to be their enemy, and himself fought against them.
The verb translated “twisted” in the ESV (διαστρέφω) refers to distorting something, departing from accepted standards, as in “perverted” (BDAG), as in “pervert justice” (LXX Exod 23:6). Paul calls this present age a “crooked and twisted generation (Phil 2:15), alluding to LXX Deuteronomy 32:5 (γενεὰ σκολιἀ καὶ διεστραμμένη), Matthew 17:17 Jesus calls them “faithless” and twisted.
If Jesus does allude to Deuteronomy 32:5, then Jesus is comparing his disciples to the wilderness generation. The wilderness generation saw God’s great miracles as he redeemed his people out of Egypt and preserve them in the wilderness, yet they constantly rebelled against God and his servant Moses.
To push this parallel a bit further, when Moses went up the mountain to see the glory of God and receive the Law, the people (the perverted generation) asked Aaron to make an idol for them to worship. When Jesus went up the mountain and is revealed as the glory of God, those who remained behind were faithless and unable to fulfill their commission and exercise authority over demons.
The present generation as witnessed God working great miracles through Jesus, and the twelve have seen Jesus reveal his glory when he walked on the water (Matthew 14:22-33). The Old Testament describes God as walking on the Sea when retelling the Exodus story. Isaiah 43:2-3 and 43:16-17 use the imagery to describe the return of Judah from Exile in a new Exodus. Psalm 77:19 describes God making a path through the sea to lead Moses, Aaron, and the people like a flock. Only God can walk on the seas. In Job 9:8, God is described as the one “who alone stretched out the heavens and trampled the waves of the sea.” The Septuagint is closer to Matthew; Job 9:8 reads “walks about upon the sea as upon the ground.”
Jesus is therefore telling his disciples they are missing out on God’s revelation in the present time in the same way the wilderness generation did after the Exodus. Like Isaiah 6:8-10, the generation who saw Jesus were “hearing, but not understanding.”