That was the burning question last night at our first Lenten Bible Study on the Sermon on the Mount. We began and ended with the Beatitudes, exploring what they meant in the historical context, in the context of Matthew’s gospel, and in the context of our own lives. The behaviors and attitudes Jesus blesses (declares happy), are they things to which we should aspire?
We struggled most with “poor in spirit.” What does that mean? One powerful suggestion was that it refers to those who are beaten down by life, dejected, depressed, hopeless. Perhaps it refers to those who are spiritually empty, or empty themselves spiritually to receive God’s grace.
Frederick Buechner proposes that the poor in spirit “are the ones who spiritually speaking, have absolutely nothing to give and absolutely everything to receive …” That fits with another theme in Matthew’s gospel, the emphasis on the weakest, most vulnerable, “the little ones” (cf Mt 18:6).
In Christian communities, our tendency is to do just what we do in the rest of life, distinguish between the proficient and the struggling, the powerful and the weak, the successful and those who fail. God’s reign entails a reversal of values. We’re somewhat comfortable when the values that are reversed are material, there’s plenty of biblical precedent for that. What if God’s reign entails a reversal of spiritual values, too? What might that mean?
Preaching Grace on the Square 
While I like what Buechner proposes, I disagree somewhat. I think his description is more aptly applied to those who are empty of the spirit. To me poor does not always mean we have nothing left to give, poor means we are running on low and we have a little bit left (For me the evidence is hope – if we can still speak of hope we have a little bit of spirit left in us) and it’s time to fill up. The disciples were at their lowest when they were grieving the loss of a relationship with Jesus. The first time when he died and the second time just before his ascension and at that time in Acts we read that Jesus breathed on them and said ‘Receive the Spirit.’ It is indeed the spirit who fills the poor (and the empty) in spirit. This is why, I believe it is so important to begin any ministry of any kind with saying “Come Holy Spirit . . . ”
I liked the cathedral in Cuernavaca, Mexico, which translated it “blessed are they with the spirit of the poor.” (They have a relief carved into the transept). Granted, I definitely like this perspective on being spiritually unable to offer anything too.