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3Blessed are the poor in spirit, for theirs is the kingdom of heaven. (Isaiah57:15)

Christ begins His sermon with beatitudes, for He came into the world to save and bless us. He came not just to provide some of His blessings for us, but to pour out all His blessings on us (Ephesians 1:3). He does it “as one having authority,” as one that can command the blessing and grant eternal life. He offers His blessing again and again, as He had promised to the repentant. He calls them “blessed and happy” and makes them so, for those whom He blesses, are blessed indeed.
The Old Testament ended with “a curse” (Malachi 4:6 [3:24]), the law of the New Testament begins with beatitude and “a blessing.” We are called to inherit His blessing.
Christ assures us, first, that nobody can enter the kingdom of heaven except through the Holy Spirit. Jesus gives us His Holy Spirit who unveils our sins and our wrong intentions. He breaks our pride that we might bow down and admit that we, the poor and miserable, are guilty and perishing before God’s holiness and appear unclean with respect to His cleanness and kindness of His majesty. We recognize our selfishness in the light of His love and our lying before the light of His truth. Blessed are you if the Spirit of God has uncovered your sins, led you into faithful repentance and cured you of your spiritual blindness. Then the gate of heaven is wide open to you for only a repentant sinner can come to God. The repentant sinner who comes to the Lord does not only enter the kingdom of heaven, but also possesses it as his inheritance eternally as it is his forever.
It is remarkable that Jesus chose his disciples only from the followers of John the Baptist. They had confessed their sins and were baptized in the river of Jordan. Only broken, repentant ones can enter the kingdom of God. The first beatitude is the unavoidable step to the riches of all the other beatitudes.

Why does “the poor by the spirit” enter into the kingdom of heaven?