Least deserving in the measures of the material world, which his disciples would often echo as they were in the process of undoing their own programing of that world. They represented those awakening from the spell/illusion of the material and would often echo its values over God's.

How often did they try to shoo away those in their estimate didn't deserve the attention Jesus, only for Jesus to admonish them for their narrow-sightedness?

Blessed are the poor in spirit, for theirs is the Kingdom of Heaven.

If in your experience people use the expression in it's positive aspects then I think that is great. In the world presented to us by it's current rulers that is not how I have seen it used.