The world’s definition of poor is to be without Gods favor, but God’s favor is clearly opposite See notes below).

www.bible.com/100/mat.5.3.nasb1995

Taken from the John MacArthur Study Bible

Blessed. The word lit. means “happy, fortunate, blissful.” Here it speaks of more than a surface emotion. Jesus was describing the divinely-bestowed well-being that belongs only to the faithful. The Beatitudes demonstrate that the way to heavenly blessedness is antithetical to the worldly path normally followed in pursuit of happiness. The worldly idea is that happiness is found in riches, merriment, abundance, leisure, and such things. The real truth is the very opposite. The Beatitudes give Jesus’ description of the character of true faith. poor in spirit. The opposite of self-sufficiency. This speaks of the deep humility of recognizing one’s utter spiritual bankruptcy apart from God. It describes those who are acutely conscious of their own lostness and hopelessness apart from divine grace (cf. 9:12 ; Lk 18:13 ). See note on 19:17 . theirs is the kingdom of heaven. See note on 3:2 . Notice that the truth of salvation by grace is clearly presupposed in this opening verse of the Sermon on the Mount. Jesus was teaching that the kingdom is a gracious gift to those who sense their own poverty of spirit.