I will venture to say that their understanding of greatness didn't come from Jesus. Rather they understood greatness from their upbringing. Jews might have been great some time in the distant past. But they were not so proud of their greatness anymore at Jesus' time. Their nation were overthrown. They were subjects to the Romans. They had to pay taxes to a hated foreign government. The practice of Roman Emperor Worship at the time probably contributed to their earthly understanding of greatness too. Hence the question: who is the greatest in the kingdom of heaven? The way the question is phrased leads me to believe they were not so much asking: would we the people of God be great? But more likely: would I the individual be great? Could I be great? What must I do to be great, greater than my rivals or greatest among my peers?
In Jesus' answer, one might get the impression that He had singled out a way to achieve this "greatest in the Kingdom of Heaven" stature. One gets the title of the greatest by being the humblest of all. Reflecting on this, I can see myself many times contriving a humble appearance to win praises, or leaving the lesser crown on the table to run for a bigger one. Many a person do that. It is a learned skill perfected by age and practice. Singularly, children in general are not very good at this game. This kind of people is outwardly humble but inwardly ambitious. He is not driven by humbleness but pride. Truly, Jesus didn't have this kind of people in mind.
Matt 18:2 said he called to him a child ... Jesus didn't pick a particular child but one who happened to be nearby. By grabbing the first child he could, Jesus referred to children in general. He then said "unless you turn and become like children, you will never enter the kingdom of heaven." The emphasis is not so much about becoming the greatest but just gaining entrance. To enter the kingdom of heaven one must be humble like children. Before one considers his stature in the kingdom of heaven, he should worry first if he is in at all. How can one be humble like children when he is already an adult? Can we roll back time? Fact is, there is nothing one can do. God alone does all things. He elected. He justified. He sanctified. He glorified. Come to think of it, Jesus was answering his disciples the same way he answered Nicodemus: one must be born again to see the kingdom of God (John 3:4).
Jesus wasn't teaching that the disciples could make themselves greatest by "humbling" themselves. He was not a guru of complete make-over. Rather, disciples had but one path to go: place themselves in the hand of God like children place their trust upon their parents. To a child, he is his father's child because his father says so. He doesn't fret about DNA testing and birth certificate. In the same way, we are children of God by faith in Jesus Christ. He said those who believe in Him has eternal life.
Is that a wonderful comfort? Is that a burden off your shoulder?
The greatest in heaven is not the best Hebrew/Greek scholar or the ablest preacher or the missionary with the longest list of sufferings ... Jesus said in Matt 7:22-23, "On that day many will say to me, ‘Lord, Lord, did we not prophesy in your name, and cast out demons in your name, and do many mighty works in your name?’ And then will I declare to them, ‘I never knew you ..."
Jesus calls out to his chosen: "Follow me." O Lord, lead me unto the path everlasting.

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