“Blessed are those who mourn, for they shall be comforted” (Matthew 5:4).
Compare Moses and the Ten Commandments with Jesus and the Sermon on the Mount. Moses spent forty days and forty nights alone on Mount Sinai, before he presented the Ten Commandments to Israel (Exodus 34:1-35:3). Jesus spent forty days and forty nights alone in the wilderness, before He presented the Sermon on the Mount (Matthew 4:1-7 cf. Matthew 5-7). The Ten Commandments were received on a mountain (Exodus 20:1-21 cf. Deuteronomy 5:1-22; Exodus 34:28). The Sermon on the Mount was delivered on a mountain (Matthew 5:1-ff). The Ten Commandments set the tone and tenor of the rest of the Old Testament (Exodus 34:27). It is a list of rules. The Sermon on the Mount sets the tone and tenor of the rest of the New Testament. It starts with attitude and will. It starts with the inner man.
The word “blessed” (makarios) is defined to mean, “blessed, happy” (Thayer); “blessed, fortunate, happy usually in a sense of divine favor” (BAG). Roland Leavell writes, “Worldly people seek happiness from without – by getting things, going places, accumulating wealth, gaining fame, enjoying popularity, having thrills… These Beatitudes give the secret to inner, spiritual happiness that is superior to circumstances” (Leavell, Studies In Matthew: The King and the Kingdom, p. 36). Eternal blessedness is found in a right relationship with God. Every other type of happiness will not last.
Blessed are those who mourn. The word “mourn” (pentheo) is defined to mean “be sad, grieve, mourn” (BAG). It is used in the New Testament for unspecified mourning or mourning in general (e.g. Matthew 9:15), mourning over the death of a loved one (e.g. Mark 16:9-10), and mourning over sin (e.g. 1 Corinthians 5:2; 2 Corinthians 12:21; James 4:9). It is neither general mourning nor mourning over the physical death of a loved one which is in view here (Though, comfort for such is available in this life cf. 1 Thessalonians 4:13-18; 5:14. Moreover, there is comfort to come for the faithful cf. 2 Thessalonians 1:3-8; Revelation 21:4). It is those who mourn over sin who are in view. Consider the context: (1) It is not those who are poor for physical or material things who are in view; but, those who are poor in spirit (Matthew 5:3). (2) It is not those who hunger and thirst for physical or material things who are in view; but, those who hunger and thirst for righteousness (Matthew 5:6). Therefore, we infer that it is not mourning over physical or material things; but mourning over spiritual matters that is in view.
Some people approve of those who practice sin. They even laugh and joke about sin. Consider: “The wicked boasts of his heart’s desire; he blesses the greedy and renounces the LORD” (Psalm 10:3). “When you saw a thief, you consented with him, and have been a partaker with adulterers” (Psalm 50:18). They “rejoice in doing evil, and delight in the perversity of the wicked” (Proverbs 2:14). They not only sin, but also “approve of those” who practice sin (Romans 1:32). They “rejoice in iniquity” (1 Corinthians 13:6). They are “puffed up” in their toleration of such ( 1 Corinthians 5:1-2). They do not blush at sin (Jeremiah 6:16; 8:12). “To do evil is like a sport” to some (Proverbs 10:23). They coarsely jest about such (Ephesians 5:4).
Those who will be blessed genuinely sorrow over sin. First, they sorrow over their own sins. It pains their hearts when they realize their wrong and guilt (cf. Acts 2:37). This sorrow caused those on Pentecost to cry out, “What shall we do?” (Acts 2:37). This sorrow causes one to produce repentance leading to salvation (2 Corinthians 7:10). Second, they also sorrow over the sin of others. The Psalmist said, “Rivers of water run down my eyes, because men do not keep Your law” (Psalm 119:136). Jeremiah said, “Hear and give ear: Do not be proud, for the LORD has spoken… But if you will not hear it, my soul will weep in secret for your pride; my eyes will weep bitterly and run down with tears because the LORD’s flock has been taken captive” (Jeremiah 13:17). Jesus wept over Jerusalem (Luke 19:41). Paul wrote, “For many walk, of whom I have told you often, and now tell you even weeping, that they are the enemies of the cross of Christ” (Philippians 3:18). Sin is no laughing matter. The blessed are tender-hearted enough to sorrow and weep over sin.
They shall be comforted. Dave Miller comments, “For those who will mourn over their sins, they will be comforted by the forgiveness that is available through Christ” (Editors Garland Elkins and Thomas Warren, The Book of Matthew, p.196, Spiritual Sword Lectureship). The forgiven can rejoice in their forgiveness (cf. Acts 8:36-39; 16:32-34).
Consider the words of the following song: “Not a shadow can rise, Not a cloud in the skies, But His smile quickly drives it away/ Not a doubt nor a fear, Not a sigh, nor a tear, Can abide while we trust and obey / Trust and obey, for there is no other way to be happy in Jesus, but to trust and obey” (Trust and Obey by J.H. Sammis).