Jesus says “”Blessed” nine times at the beginning of the teaching starting in chapter 5.
We look at this list, which is called the beatitudes, and try to figure out what Jesus meant. Actually, I think, we try and figure out how we can be part of the list.
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 want to know what poor in spirit means.
Does it relate to bank accounts, in which case it turns our usual expectations upside down (don’t have money in the back? You have heaven!). Does it mean spiritually needy, in which case it applies to everyone. Does it mean recognizing spiritual inadequacy?
Once we know the rules, then we can get what is in the formula.
I think that it isn’t that easy. I think that Jesus is being descriptive (for example, people who are poor in spirit are blessed, because they will not be spiritually poor), rather than prescriptive (If you want to get the kingdom of heaven, then be poor in spirit).
Here’s what I think was happening on that hillside.
Jesus sat down up on a hillside. His closest friends came and sat down with him. He looked around at their faces. He looked around at their hearts. And he knew what was in each.
And he started to talk. As he looked first at one of the disciples, one that everyone knew was struggling with a really bad sense of himself. He was constantly despairing of ever measuring up spiritually in this group.
Jesus looked into the disciple’s face and said, “blessed are the poor in spirit.” The disciple looked up, full of hollowness. “Theirs is the kingdom of heaven.”