Jesus says “Blessed” nine times in the first few sentences of chapter 5. We look at this list, which is often called “The Beatitudes,” and we try to figure out what Jesus meant. Actually, I think, we try to figure out how we can be part of the list.

We want to know because we like clear rules for success. Once we know the rules, then we can get whatever is in the formula.

But I think that when Jesus gave this list of blessings, he wasn’t creating a formula or a list. I think he was describing hope for people who are wrecked rather than creating formulas for people who think they’re fine. The hard part of this teaching is that most of us don’t want a new routine until we believe at our core that the old one and all its variations will still leave us poor in spirit.

For example, Jesus says that the poor in spirit will be blessed, that they will have the kingdom of heaven. So, wanting to have the kingdom of heaven, we ask what poor in spirit means. Does it relate to bank accounts, in which case it turns our usual expectations upside down (It sounds like an infomercial: “Don’t have money in the bank? Don’t worry your little soul. You have heaven!”)? Does it mean being spiritually needy, in which case it applies to all of us even if we don’t see it?

Here’s what I think was happening on that hillside:

Jesus was walking with his followers near his hometown. He sat down on a stone on a hillside. His closest friends came and sat down with him. He looked around the circle. Others stood around the circle. He took time looking at their faces. He looked around at their hearts. And he knew what was in each.

The sky was clear, the Sea of Galilee was visible in the distance. He looked at one of the disciples, one that everyone knew was struggling. He had no interest in the view. His heart was aching. This man was despaired of ever measuring up spiritually in this group.

Jesus looked at the disciple and said, “Blessed are the poor in spirit.” The disciple looked up, face drawn, eyes quizzical. “Theirs is the kingdom of heaven.”

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From Matthew 5:1-2