What Did Matthew Mean By "Blessed" in Matthew 5?

     “Makarios”, Translated "blessed" here in Matthew 5:1–10, in Greek means “fortunate” or “happy” and is derived from the root "mak", which means “lengthy.” Perhaps the Greeks saw blessedness as related to the idea of “length of life”—a long life was a blessed one.
Makarios was frequently used in Greek literature, the Septuagint (a Greek translation of the Old Testament), and the New Testament to describe the kind of happiness that comes from receiving divine favor. Consequently, the word can also be rendered “favored.” In the New Testament it is usually a divine passive; this means that people are blessed by God. The Lord God is the One who is blessing or favoring the person.
     The most well-known “blessings” are described in the Beatitudes, wherein we see the various kinds of blessings God gives to those who are worthy of these graces. The Beatitudes are written in two different forms: one in Matthew 5:3–12 and the other in Luke 6:20–23. The pronouncement of the blessings in Luke is done immediately after the selection of the twelve disciples (Luke 6:12–16). Yet, the sermon is addressed to the crowd generally and speaks of the advent of God’s kingdom. Luke balances four blessings with four woes—changing from the present tense to the future tense—to heighten the contrast of the impending reversal of social conditions.
     In Matthew’s account, the kingdom has already begun, indicated by the use of the present tense. These Beatitudes are addressed to the disciples particularly and are not a general proclamation. They are more concerned with the interior life of the disciple—to activate here and now the kind of life Jesus communicates in those who follow Him. The eight Beatitudes reflect on the traits of those who belong to that kingdom and who therefore reflect Christ’s own life. Read, for example, this passage in Matthew 5:1-10...
     The people and situations described may seem bad by our human standards. Yet, because of God’s presence in our lives, we are actually blessed by God through these trying situations.

From the Holman Treasury of Key Bible Words