In short, to be “poor in spirit” means to see ourselves as we really are before God. It is a recognition that we inherently have nothing that would commend us to Him, that we are spiritually bankrupt and destitute. We have no claim on His mercy. He owes us nothing. We deserve nothing but hell, and we can’t do anything about that reality on our own. And Jesus says we are “blessed” when we realize that fact.
For years, the Sermon on the Mount (Matthew 5-7) was one of the most difficult passages of Scripture for me to read. The reason had nothing to do with an inability to understand the message that Jesus is sharing. His words are quite clear. No, my issue had everything to do with being completely overwhelmed by His teachings and feeling condemned to failure before I even started.
In the Sermon on the Mount (Matthew 5-7), Jesus defines what it means to live a “radical” Christian life and to truly be great in His Kingdom. What He tells us in these chapters is not just the best way to be great and live radically — it is the only way.