Mat 5:3 Blessed [are] the poor in spirit: for theirs is the kingdom of heaven.
Alternative: Fortunate those who beg for breath for the kingdom of heaven is theirs.
The most obvious meaning of this line is that those who ask for spirit will win heaven. This is consistent both with the idea of "those who ask shall receive" and, in a larger sense, with the idea that the purpose of our temporary lives is to transform our bodies, mind, and emotions into spiritual growth (discussed here).
The word "blessed" in Greek is makarios which is from the base makar, meaning "happy" or "fortunate" but with the sense of favored by God. It can also mean "wealthy" with andros makaros (fortunate men) meaning specifically "the wealthy" (men with a fortune). This sets up an interesting play on words that only works in Greek, saying "wealthy are the poor."
However, the line doesn't quite say "the poor." It says "the poor of spirit," which comes from the Greek, ptochos pneuma (see definitions below). Ptochos means "poor" but in the sense of a beggar. When combined with another word like pneuma the term can also means "lacking." Pneuma in Greek means literally "breeze" or "breath" and in other Greek literature didn't primarily mean "spirit" until the Gospels but it was the word used in the Septuagint (the Greek version of the OT from Christ's times). Another Greek term used much more commonly for spirit, thumos, also means breath, and life force, but it has a sense of maleness and aggressiveness.
In the Bible, pneuma is equated with the Hebrew ruah (ruwach) which also means "breeze" or "breath" and is used to mean the breath of God, the movement of the invisible divine spirit. "...the breadth of God moved upon the face of the waters." (Gen 1:2). Christ quotes Isa 61:1 saying "the breath of the Lord God is on me" when he announces his priesthood.
Ruah is the term used to indicate difference between physical and spiritual. The Old Testament says God is ruah, that is, spirit, not a physical being. In the Septuagint, pneuma is used in place of ruah. In the Gospels, it is the specific term used for the Holy Spirit, but it is also used to mean the human spirit. It is also the term used in the Gospels to described the evil spirits that Christ casts out.
This phrase ptochos pneuma could mean anything from those lacking the spirit of God to those lacking evil spirits or even those short of breath. In other words, this is a very difficult line. How do we decide what it means? As the first line of his first sermon, I am not comfortable with my inability to pinpoint Christ's exact meaning. However, I think this uncertainty is exactly what makes Christ's teaching so interesting compared to the teaching in most holy books.
If ptochos pneuma indicates those people who feel that they are lacking God's spirit, in other words, those who lack certainty about God, (which is the feeling I have about this phrase itself) this idea relates to the second test of Christ where we are told that we cannot test for proof of God. If ptochos pneuma indicates those who feel that they lack their own animating spirit, it could mean those who rely on the spirit of God rather than their own egos. If ptochos pneuma means those who are not controlled by evil spirits, it means people whose mind is not troubled. More simply, if ptochos pneuma means those who lack breath in the physical sense, the statement describes those whose time is short here on this earth.
Personally, I think that Christ means all of these things, including other ideas that are not as obvious. All of these people are moving toward that great mystery of the kingdom of heaven, the rule of the universal, the realm of God. The fact that the phrase itself has a lot of different dimensions is what separates Christs words from everything else ever taught.
"Blessed" is from makarios (makarios) which means "blessed," "happy," and "fortunate."
"Poor" is from ptôchos (ptochos), which means "beggar," "beggar-woman," and "beggarly."
"Spirit" from pneuma (pneuma), which means "blast," "wind," "breath," "the breath of life," and "divine inspiration."
"For" is from hoti (hoti), which means "for what," and "wherefore."
"Theirs" is from autos (autos), which means "the same," and the reflexive pronouns, "myself," "yourself," "himself," "herself," "itself," or the oblique case of the pronouns, "him," "her," and "it." It also means "one's true self," that is, "the soul" as opposed to the body and "of ones own accord."
"Is" is from eimi (esti), which means "to be," "to exist," "to be the case," and "is possible." (3rd person, singular present form-esti).
"Kingdom" is from basileia (basileia), which means "kingdom," "dominion," "hereditary monarchy," "kingly office," (passive) "being ruled by a king," and "reign."
"Heaven" is from the Greek ouranos (ouranos), which means "heaven as in the vault of the sky," "heaven as the seat of the gods," "the sky," "the universe," and "the climate."