Variety: Luke 6v20

Blessed are you who are poor,
   for yours is the kingdom of God. (Luke 6:20)

Blessed are the poor in spirit,
   for theirs is the kingdom of heaven. (Matthew 5:3)

The kingdom of God on earth is Jesus’ specific proposal to humanity. While the Sermon on the Mount is not a complete statement of the proposal (it takes all four Gospels for that), it does contain many of the major points. So it is quite natural at the very beginning for Jesus to deal with the question of how to enter the kingdom, or how to become a citizen of it.  
The first seven Beatitudes [Matthew 5:3–9] do just that. They are steps into the kingdom, the stairway to spiritual life…. These are not blessings pronounced upon different kinds of people—the meek, the merciful, the pure in heart, and so on. Rather, they are stages in the experience of only one class of people—those who are entering the kingdom and who at each stage are blessed. The kingdom, of course, is the blessing, and each step into it partakes of its blessedness. This blessedness comes with the taking of the step, and is not postponed as a future reward. Jesus said, “Blessed are…”.  
The first step in becoming a son or daughter, or being begotten from above, or in entering the kingdom, or being saved, or finding eternal life—whatever term you wish to use—is stated by Jesus as:  
“The poor in spirit are partakers of the divine blessing, for theirs is the kingdom of heaven” [Jordan’s translation]. 
What does Jesus mean by “poor in spirit”? In Luke’s account it is simply “you poor.” What kind of poverty is he talking about? If you have a lot of money, you’ll probably say spiritual poverty. If you have little or no money, you’ll probably say physical poverty. The rich will thank God for Matthew; the poor will thank God for Luke. Both will say, “He blessed me!” Well, then, who really did get the blessing? 
Chances are, neither one. For it is exactly this attitude of self-praise and self-justification and self-satisfaction that robs people of a sense of great need for the kingdom and its blessings. When one says, “I don’t need to be poor in things; I’m poor in spirit,” and another says, “I don’t need to be poor in spirit, I’m poor in things,” both are justifying themselves as they are, and are saying in unison, “I don’t need.” With that cry on their lips, no one can repent…. 
It is neither wealth nor poverty that keeps people out of the kingdom—it is pride.  
So the poor in spirit are not the proud in spirit. They know that in themselves—in all people—there are few, if any, spiritual resources. They must have help from above. They desperately need the kingdom of heaven. And feeling their great need for the kingdom, they get it.  

Clarence Jordan