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Jesus expected his disciples to have sufficient faith to repeat his miracles by this point (vv. 16-17, 20). Unbelieving . . . generation (v. 17) applied generally to Jesus' contemporaries (11:16; 12:39-45; 13:39, 45; 16:4; 23:36; 24:34), but in this case specifically to his disciples, who proved unable to stand in for him in his absence (17:16). Disciples were by definition apprentices in training to assume the role of their teachers. Jesus had already sent his disciples out, and they had healed the sick and driven out demons (10:8). Had they not seen enough to believe (compare 8:26)?
Matthew expected his audience to learn from these recorded signs of Jesus, just as the first disciples did when they witnessed them. We who read these accounts in the Bible should be growing in our faith relationship with Jesus, as the disciples did who first walked with him. How often do needs around us go unmet because we neglect radical trust in God, especially on behalf of others' needs?