The most unsettling aspect of his alternative wisdom, and perhaps the most consistent, is that the outcast is in the head-start position, precisely because he or she has been excluded from the false sacred system—the only game in town. Jesus thus begins with a most incredible statement: The poor are the blessed ones! (See Matthew 5:3.) Life has already freed them from the lie that the rest of us cannot see. They are potentially turned around and given a symbolic advantage in hearing the truth: “I tell you, tax collectors and prostitutes are making their way into the Reign of God before you” (Matthew 21:31). If the system is a mess, those outside of it are at a significant advantage.
—from the book Jesus’ Alternative Plan: The Sermon on the Mount
by Richard Rohr, OFM