Before Jesus chooses anyone, he prays. 12"All night he continued in prayer to God," and only after that night does he call his disciples and choose twelve to be named apostles. Fishermen, a former tax collector, a Zealot committed to resistance against Rome alongside the man who profited from Rome, and last, with no softening, 16"Judas Iscariot, who became a traitor." Jesus prayed all night and still chose him. A whole night of prayer produced twelve ordinary men, chosen anyway.
Coming down from the mountain he meets a crowd gathered from everywhere, 17"all Judea and Jerusalem and the seacoast of Tyre and Sidon." Tyre and Sidon were old Phoenician coastal cities outside Jewish territory. The crowd needing him has outgrown any nation's borders, and 19"power came out from him, and healed them all." The same power moves later when a bleeding woman touches his garment (Luke 8:46). It goes outward because people press close enough to receive it.
Then, before that crowd, Jesus turns to his disciples and says what upends nearly every ordinary measure of a good life. 20"Blessed are you who are poor." 21"Blessed are you who are hungry now." "Blessed are you who weep now." 22"Blessed are you when people hate you." Four blessings, each naming a condition any reasonable person calls misfortune. And Luke alone pairs each with its opposite: 24"Woe to you who are rich." "Woe to you who are full now." "Woe to you who laugh now." 26"Woe to you, when all people speak well of you." "Woe" is old prophetic vocabulary, the funeral cry Isaiah pronounced over the greedy (Isaiah 5:8-23) and Habakkuk over an empire built on plunder. Jesus takes the oldest prophetic form there is, grief spoken in advance over a fall not yet visible, and aims it at the comfortable and well regarded.
Matthew's version of this sermon softens the blessings toward the spiritual: poor in spirit, hungering for righteousness. Luke does not. His poor are poor, and his hungry are hungry. Mary has already sung of a God who fills the hungry and sends the rich away empty, and here Jesus states the same reversal as plain doctrine.
The logic under each pairing is that the present condition of both groups is about to be reversed by the kingdom he is bringing, completely. The poor inherit a kingdom no wealth could buy. The hungry are satisfied beyond one meal's relief. Those who weep now will laugh. And those who have already received all the world had to give, comfort, fullness, laughter, approval, 24"have received your consolation" already, in full, with nothing further coming. The warning is that these things can become a full payment cashed out in this life. Nothing here says wealth or laughter or popularity is itself sin.
The last woe is the strangest and most searching. Being spoken well of by all should make a person suspicious, because the false prophets of every generation were nearly always the popular ones. Being loved by everyone was never the safe position Jesus' crowd assumed it to be.
Ask what comfort or approval you have mistaken for the whole of your reward.
Prayer
Father, thank you for a kingdom whose measures run so completely against the world's. Teach us to trust that the poverty, hunger, grief, and rejection many of your people carry now are not the last word you intend to speak over them. And keep us, whatever comfort or approval we hold, from mistaking it for the whole of our reward, when so much more is waiting to be given. In Jesus' name, amen.