In this series of exhortations focused on God’s blessings, it would have been more awkward not to reference the beginning of the Sermon on the Mount. When Jesus sat down to teach He began with what we call the “Beatitudes,” so named due to the Latin word beatus which means “blessed.” Nine verses in a row start with the Greek word makarioi, translated by the plural form beati in the Latin Vulgate, and “blessed” in English. In the orchard of God’s blessings, these nine trees are planted closely together.
Skipping over the first in the list at the moment, here is Matthew 5:4. “Blessed are those who mourn, for they shall be comforted.” Paul uses the same word for mourning (pentheo) in 1 Corinthians 5:2 in reference to how the church should respond to flagrant sin in her midst. Jesus uses it about those who are constantly mourning.
Matthew doesn’t record the reason for mourning, so perhaps it refers to any kind of sadness. But there is good reason in the sermon context to understand it as a grief for sin. That’s certainly true in the Corinth context. A man feels sorrow for the loss of holiness, which he was made to have. He grieves that he has caused insult to God.
Of all the blessings, this one seems the most difficult to connect. Happy are the ones who are sad? But that’s what Jesus says, and it’s not just because of the promise. Yes, those who mourn “will be comforted,” but if comfort was the only piece of blessing, wouldn’t the beatitude need to say, “Those who mourn will be blessed with comfort”? The comfort is blessing, but so is the mourning itself.
Mourning is part of the blessing because it means we see something as God does, and because we’re sharing His reaction to it. Those who are deluded or who are distracting themselves are not blessed, neither are those denying the truth. The blessing is as deep, or shallow, as the mourning.