In a series of denunciations, each beginning with the formulaic “woe to you,” Jesus is the Messiah whose life, death, and resurrection are God's saving act for humanity chastises the leaders who fail to follow the teaching of the Messiah-that greatness means to be a servant and that it is those who humble themselves who will be exalted.
In this lengthy series we hear Jesus’ criticism of leaders who in their actions fail to live up to what they teach. As such, the “woes” pronounced are negative mirror images of the “blessings” of the Sermon on the Mount and the actions described are a failure to exhibit the congruency of “hearing” and “doing” for which it calls.
The harsh criticisms of the hypocrisy of the scribes and Pharisees have often led readers to unfortunate stereotyping of these Jewish leaders. But Jesus clearly switches in 23:8-12 to address Matthew’s contemporary hearers about what it means to follow the The Messiah was the one who, it was believed, would come to free the people of Israel from bondage and exile. In Jewish thought the Messiah is the anticipated one who will come, as prophesied by Isaiah. In Christian thought Jesus of Nazareth is identified.... The double reversals of greatness and being a servant, of exaltation and humility, recall important themes of the call to discipleship in the kingdom. How will this community address its challenges in the face of the risk that religious tradition becomes an end in itself? Matthew’s community has “one Father…in heaven” and “one Teacher” who is the Messiah. This teacher models humility and compassion, in light of which they, too, are called to the compassion of brothers and sisters (23:8; the NRSV translation “students” is clearly mistaken; the original Greek here reads “brothers and sisters”). The conclusion of the chapter with Jesus’ lament over Jerusalem, his expression of compassion for God’s children, and his longing for those who will see his coming as a sign of God’s Blessing is the asking for or the giving of God's favor. Isaac was tricked into blessing Jacob instead of his firstborn Esau. At the Last Supper Jesus offered a blessing over bread and wine. To be blessed is to be favored by God. certainly recall John’s earlier question and the issue of response to Jesus as one of blessing or offense: “Are you the one who is to come, or are we to wait for another?” (11:2-6).