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It is one thing to be spiritually poor and acknowledge it, as the first beatitude says; it is another thing to grieve and mourn over it. In more theological language, confession is one thing, contrition is another. One might almost translate the second beatitude "Happy and the unhappy" in order to draw attention to the startling paradox it contains.
"Blessed are those who morune for they will be comforted." (Matthew 5:4)
It is plain from the context that those Jesus promised comfort are not primarily those who mourn the loss of a loved one, but those who mourn the loss of their innocence, their righteousness, their self-respect. It is not the sorrow of bereavement to which Christ refers, but the sorrow of repentance.