Jesus purposefully sequenced the Beatitudes in this order because this is the way we grow in sanctification. First, we see our bankrupt condition (Matthew 5:3) then it breaks our heart (Matthew 5:4).
This word “mourn” speaks of the strongest kind of lamentation, not just a sentimental tear. What we need today are men and women who are broken over their sin.
Proverbs 14:9 says, “Fools make a mock at sin: but among the righteous there is favor.” Jesus speaks of this favor when He says that we will be comforted. The Holy Spirit is our Comforter who will strengthen us when we are broken over our sin.
Do you know where we ought to be? On our face before God in bitter tears over the barrenness of our lives, the coldness of our hearts, and the wickedness of our attitudes. And what will be the outcome? We will be comforted.