Poor vs. Poor in Spirit

I was doing a Bible study last month in which we went through the Beatitudes together. One of the questions that came up was the fact that Luke says “Blessed are the poor” whereas Matthew says “Blessed are the poor in spirit.” So which is it? Are all the poor blessed or just those who are spiritually impoverished or what?
So I started poking around and found a wonderful resource answering this question from Hans Kvalbein: http://s3.amazonaws.com/tgc-documents/journal-issues/12.3_Kvalbein.pdf

He does such a good job explaining that I’m not going to even attempt a summary but will just share key highlights: 

“The beatitudes of Luke are not in the third person [they], but in the second person plural [you all]. His beatitudes are directed to ‘you poor,’ to a specific group Jesus has in front of him. The context leaves no doubt as to whom Jesus is speaking: ‘Looking at his disciples, he said…’ (v. 20). The message of Jesus according to Luke is not that everybody who is poor is blessed, but that the disciples, in spite of their bad condition now, are blessed because they are receivers of the kingdom of God.”
The beatitudes seem to be drawing from a particular passage in Isaiah 61, which is “a promise to the ‘poor,’ the ‘brokenhearted,’ the ‘captives,’ the ‘prisoners’; it is a word of comfort to ‘all who mourn’ and ‘those who grieve in Zion.’ …When we look at the content and the wider context of Isaiah 61 it is evident that the promise refers to Israel as a whole. It does not refer to a limited group of the economically poor within the people, nor does it refer to all the poor and destitute in the world.” (Note well, here, that Christians consider ourselves to be in the lineage of Israel, that is that the Israelites were the “people of God” under the Old covenant and Christians have been “grafted into” this family tree (cf. Romans 11).  This would mean that the promises to the poor/afflicted of Israel apply to the poor/afflicted in the church.)
“The meaning of the word ‘poor’ here is not the economically poor, destitute, or needy… ‘Poor’ here means ‘helpless’, dependent on others, unable to pay back. The recipients are in this word indeed described as beggars. But the word does not refer to their economic or social status. The tax collectors, the fishermen, and the farmers in the fellowship around Jesus were certainly no beggars and could hardly be called ‘poor’ in a material or social sense of the word. They were able to sustain themselves by their own work. But they were beggars before God. They were dependent on his grace as it was proclaimed and demonstrated in the preaching and person of Jesus. The word is used in a transferred sense and describes the fundamental position of man before God.
One of Martin Luther’s last words was this: ‘We are beggars, that is true.’ As far as I know, Luther had never been a beggar in the literal sense of the word. But he had learnt both from Scripture and life that we are dependent on God, we are beggars before him. The gospel is the message that God gives his gift, his kingdom, to beggars, into empty hands. We have nothing with which to pay him back.”
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