Jesus has just warned them of the ravenous religious leaders, hungry for power and status, and now onto the scene comes a ravenous woman, famished from poverty-stricken hunger. The religious leaders devour womens houses (Lk. 20.47), and hers could have been one of the ones they stole (or at least she typifies their typical victims). In the midst of all the showy religiosity sneaks a woman with a humble heart (Cf. Lk. 6.20-21: Blessed are you who are poor, for yours is the kingdom of God. Blessed are you who hunger now, for you will be satisfied. Blessed are you who weep now, for you will laugh.)
(Just as an aside, I notice in the book of Luke, Luke speaks favorably and redemptively of women throughout his whole gospel: Elizabeth, Mary, Anna, Simon’s mother-in-law, the widow of Nain, the bleeding woman, Jairus’s daughter, Mary and Marth, etc etc etc. The women were fearless devoted after the crucifixion, and were the first witnesses of the resurrection. People who accuse the Bible of misogyny haven’t read it and don’t understand it.)
The outbreak of contrasts continues: the men of respect and the woman of indignity, the excessively rich and the immensely poor, the generous gifts and the pathetic coins. But Jesus notices it all, and he praises her. This is an outrageous example of the last shall be first and the first last, and those who humble themselves will be exalted, and those who exalt themselves will be abased. In an honor and shame culture, she, who has likely known only shame her entire life, receives honor from the lips of the Son of God himself, compassionate in his mercy and prolific with his praise. While all in their culture were taught to disregard a person of such low estate, Jesus not only notices her, but honors her. Its the great reversal of the kingdom of God and the upending of all things earthly.
Jesus is relentless in his teaching of a “hazardous liberality,” as Piper calls it. He seems so tickled by any behavior that mirrors his torrent of grace and his teeming love. Most of us would call her stupid, or if we were more “politically correct” in our sensitivities, irresponsible. A poor steward. Short-sighted. Piper says, “The point here is not that everyone should give everything away. The point is: Jesus loves faith-filled risk for the glory of God.”