Dear Peter,
Thanks for the question.
Jesus often uses hyperbole to make a point, so in a way he is exaggerating to a degree to make people think. Abraham, Moses, King David, Solomon, Caesar, no matter how glorious or great any of those figures were, they had nothing on John. He is literally reshaping how we think about greatness. John was poor and humble, dressed like a homeless person. He was not what anyone would consider great. That is simply how we view things in the natural order.
So, First, Jesus was not comparing John to Mary in any kind of direct or even indirect way; He was making a statement of the stature of someone who may be considered (inglorious|not glorious) in the natural order.
Secondly, the fullness of the point comes in the second part which follows, but the least born in the kingdom of God is greater than he. Clearly, in the order of grace, Mary ranks supreme. Of all mankind, Mary was singularly conceived within the order of grace; in essence, in the kingdom of God from conception, for the Holy Spirit brought to her that special grace merited by her Son.
If Jesus' point were completely literal, to the last man or woman, He Himself would be inferior to John, because He was born of a woman.
Peace,
Bob Kirby
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