The paradox of the second beatitude is obvious. What could be more self-contradictory than the idea that the sad are happy, that the path to happiness is sadness, that the way to rejoicing is in mourning?
Remember, this is not a subjective statement identifying how a person feels. Instead, it is an objective statement identifying how God sees a person.
Nine different Greek words are used in the New Testament to describe sorrow. Of the nine terms, this is the strongest and most severe (pentheo).
It represents the deepest, most heartfelt grief and was generally reserved for grieving over the death of a loved one. It was used in the Septuagint (Greek translation of the Old Testament) to describe Jacob’s grief when he thought his son Joseph was killed by a wild animal. “so Jacob tore his clothes and put sackcloth on his loins and mourned for his son many days” (Gen. 37:34).
This is speaking of the sorrow of repentance. It is one thing to be poor in spirit and acknowledge it; it is another to grieve and mourn over it. Or to put it another way, it is one thing to confess sin, it is quite another to be broken over that sin This refers to a deep inner agony.
Those who are blessed—that is approved by God—will:
The result of godly mourning is comfort. “Comforted” comes from the greek, parakaleo, the same word that, as a noun, is rendered Comforter, which is one of the descriptors of the Holy Spirit. The emphatic pronoun (they) indicated that only those who mourn over sin will be comforted. The blessing of God’s comfort is reserved exclusively for the contrite of heart. The fact that a present participle is used in this verse indicates continuous action. In other words, those who are continually mourning are continually comforted.
Notice the comfort is actually immediate. For those who truly mourn, their comfort is not delayed. Also, the basis of comfort is forgiveness, the Holy Spirit, and salvation. When a person is broken over her sin and turns to Jesus in faith, forgiveness rushes in, the Holy Spirit indwells her, and salvation is found. This is true comfort; this is true joy. The way to a jubilant heart is mourning. Don’t be deceived by the world that will tell you, “let us eat, drink, and be merry for tomorrow we die.”
When David stopped hiding his sin and began mourning over it and confessing it (Psalm 32:3-5), he could declare, “How blessed is he whose transgression is forgiven, whose sin is covered! How blessed is the man to whom the Lord does not impute iniquity, and in whose spirit there is no deceit!” (Psalm 32:1-2).