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The third Beatitude is found in Luke 6:21, “Blessed are you who weep now, for you shall laugh.” Matthew words it differently in Matthew 5:4, “Blessed are those who mourn, for they shall be comforted.”
How can it be that those who mourn or weep are considered “blessed?” Our natural instincts avoid pain and any occasion for sorrow. But perhaps Solomon understood the meaning of this when he wrote in Ecclesiastes 7:2-4,
2 It is better to go to a house of mourning than to go to a house of feasting... 3 Sorrow is better than laughter, for when a face is sad a heart may be happy. 4 The mind of the wise is in the house of mourning, while the mind of fools is in the house of pleasure.
Those who never experience pain in life never truly mature in their character. Those who live for their own pleasure remain shallow and immature, unable to empathize with others who mourn, because they have never experienced it for themselves.
The truly blessed ones are overcomers. These are people who have had much to overcome, and by facing those problems, hardships, and sorrows of life, they have depth and maturity.
Abraham and Sarah had no children for decades, and no doubt this caused them pain. There is little doubt that Sarah wept before God, seeking the fulfillment of the promise. When she passed through menopause and could no longer bear children, she must have had to face the “reality” that either the promise of God had failed, or He would have to give her children in another way.
She tried to fulfil the divine promise through Hagar, but when Hagar became haughty, it only caused her more pain. Finally, when she was 90 years old, God fulfilled His promise to her, and she brought forth Isaac, the son of promise. She called him Isaac, “laughter,” because her mourning had been turned to laughter.
Matthew’s word for “mourn” is pentheo, “to lament or wail.” Because Luke uses the word “weep” (kleio, “to mourn, weep, lament”), we have two words to solidify Jesus’ meaning. The word pentheo is often used in connection to death and funerals, but also when men repent and lament for their sin.
The Apostle Paul says in 1 Corinthians 5:1, 2,
1 It is actually reported that there is immorality among you, and immorality of such a kind as does not exist even among the Gentiles, that someone has his father’s wife. 2 And you have become arrogant, and have not mourned [pentheo] instead, in order that the one who had done this deed might be removed from your midst.
It is the mourning of repentance. James 4:9 also applies pentheo in the same way.
So the Beatitude includes not only mourning and weeping on account of pain and suffering, but also repentance for sin or a sinful condition. Hence, the Day of Atonement was a day of fasting and repentance, and fasting was said to be time of “mourning.”
Joel 2:15-17 speaks of fasting on the Day of Atonement, saying,
15 Blow a trumpet in Zion, consecrate a fast, proclaim a solemn assembly… 17 Let the priests, the Lord’s ministers, weep between the porch and the altar, and let them say, “Spare Thy people, O Lord…”
Isaiah’s commentary on the Day of Atonement is found in Isaiah 58, where the prophet gives us the true meaning of this day of fasting and prayer. He shows that God is not so interested in men abstaining from food (Isaiah 58:5), but rather in setting men free, feeding the hungry, and helping the needy (Isaiah 58:6, 7). And then, because the Day of Atonement was also a Sabbath, Isaiah concludes his commentary by telling us the true meaning and purpose of a Sabbath. It is to cease from one’s own labor and do only the works of God (Isaiah 58:13). This is how we enter God’s rest (Hebrews 4:10).
All of these concepts are bound up in Luke’s third Beatitude. We labor to enter rest, we weep now to enjoy true joy and laughter in the end, we repent now so that the Holy Spirit may conform our lives to the example of Jesus Christ. The labor, weeping, and repentance are not ends in themselves, but are the means to an end.
In contrast, “the rich,” who have the means to avoid most pain and the luxury of pursuing pleasure, are not the blessed but the “woed.” Luke 6:25 says, “Woe to you who laugh now, for you shall mourn and weep.” Jesus was not chiding those who laugh or make jokes, as some have thought. He was speaking of the pursuit of pleasure and the avoidance of pain. These go through life with no empathy for the needy and feel no need to change one’s attitude or behavior.
Because most of the needy think of the rich as being blessed, Jesus turned it around. Being blessed was not connected to wealth but to one’s character and spiritual maturity. Hence, it is usually easier to develop spiritual maturity and to manifest the love of God while in need than in the midst of wealth.
Finally, the Holy Spirit (“Comforter” in the KJV, or “Helper” in the NASB) is connected to mourning (repentance) as well. John 16:8 says of the Spirit,
8 And He, when He comes, will convict the world concerning sin and righteousness, and judgment.
It is the job of the Holy Spirit to show us the right path. The Spirit also interprets the Word for us and shows us how to apply it correctly in our lives. To repent means to change one’s mind and behavior. The Holy Spirit’s revelation helps us to make changes in our perspective, our opinions, our understanding, which then translate into changes of action in our daily lives.
This is foreshadowed in Isaiah 61:2, where the Messiah’s calling, in the end, was “to comfort all who mourn.” The word “comfort” is from the Hebrew nakham. This is the word from which John derived the concept of the “Comforter” in relation to the Holy Spirit. When Isaiah 40:1 says, “Comfort, O comfort My people,” it prophesies of the coming of the Holy Spirit after the Mediator-Messiah had ratified the New Covenant.
Matthew’s version of the Beatitude says “they shall be comforted,” using the Greek verb parakleo. The noun form of this word is parakletos, “Comforter” or “Helper.” Mourning, then, brings the Holy Spirit to comfort us and help us, rewarding us with revelation.