Matthew 5:19

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The kingdom of heaven is synonymous with "the kingdom of God," which is to say it names or describes the reign or the dominion of God. It is more than a peculiar geography or population; it is an administration of personal, sovereign authority. The kingdom of God once had an Old Covenant manifestation that originated at Mt. Sinai. God, the King, established his covenant (administration) over his people Israel. He was their one, only, eternal King. His presence moved from the top of Sinai to the Holy of Holies in his royal pavilion, and he went with and before and behind his people, shepherding them to a homeland.

By the time Christ was due to appear for the manifestation of the divine kingdom more nearly than ever before, Israel as the visible kingdom had gone through many stages. There was even a sense in which the kingdom of God was seen as having been "removed" from its situation amid the covenant nation, as the disciples inquire in Act.1:6, “Lord, will You at this time restore the kingdom to Israel?” By this question, they showed that even in the aftermath of the resurrection of Christ those who were "great" in the Lord's kingdom still showed a kind of naive perception of Jesus' New Covenant administration of the kingdom of heaven.

Well prior to that moment, Jesus aimed to correct such errors as in e.g. Mt.18:1-5. He continued to correct in this vein as in Mt.19:13-15, and Mt.20:20-28. "Greatness" in his kingdom--in the realm of his administration--is not measured in ways analogous to earthly metrics. As he said in another place, Lk.22:27 "For who is greater, he who sits at the table, or he who serves? Is it not he who sits at the table? Yet I am among you as the One who serves." Clearly, King Jesus is greater than any other in his own kingdom; but he does not establish his authority by displays of wealth, by making friends and loyalists through distribution of gifts, or by awesome and dread-inducing miracles; but by selfless ministry, by seeking the good of his people regardless of personal cost.

His counsel to his disciples is to follow his example, Jn.13:15. There is "status" in the kingdom of heaven, just as there is "office" that men hold in trust from the king. But having such office is clearly no reason whatever to demand from other men one's "rank." That is what kings and great men outside the kingdom expect but not what those inside it should, note the comparison Mk.10:42-45. Those who are "lesser" in the kingdom would, in general, be those who act contrary to the character of their king. In earthly terms, if one belongs to the kingdom of heaven in fact, but speaks and acts like he belongs to the kingdom of the world--this one clearly is immature and unworthy.

In Mt.5:19, Jesus there employs the teaching rhetoric of hyperbole. He trades on his audience being familiar with regular trappings of life in the world, of life in the visible administration of Old Covenant Israel (such as remained to it, while it was under foreign worldly dominion). Men of status in Judea and among the Jews distributed near and far in the world--party leaders, ranking priests, men of wealth, and the like--they wanted and loved recognition and deference, cf. Mt.6:5; Act.23:1-5. We should doubt if Jesus meant to imply that false-professors and false-teachers were welcome at all where his program was instituted. Likewise, we should doubt if Jesus meant to imply that possible, perfect Old Covenant lawkeepers (better than Pharisees! v20) were bound to possess the highest status in the New Covenant.

At the same time, it should be clear that Jesus commends as his sincerest disciples those who take his word of command most seriously. Who gets this king's attention is not the man with the "most" to offer the king, in the way of dedicated wealth or influence. Rather, it is he whose heart belongs to the king, and who understands the requirement of immaculate obedience. The Pharisees, for all their efforts, had no heart for God (Is.29:13); and their teaching per the Law of Moses was an exercise in hypocrite-making, Mt.23:15. Truth be told: it was Jesus alone who did and taught perfectly according to what had been delivered to Moses by the mouth and finger of God. He only deserves that title, "Great," in true covenant-of-grace terms.

Those who love God, who love Jesus, they will seek despite their inadequacy to conform to the will of God. God will aid them. They will say to God, "You have also given me the shield of Your salvation; Your right hand has held me up, Your gentleness has made me great," Ps.18:35. It is a Spirit-empowered diligence, the power of Christ, that perfects the imperfect commitment of his people, that makes their righteousness exceed the most intense but earthly power of obedience what fails its test. The Pharisees were "least" in the real kingdom, the kingdom that was replacing the one where they had been "great." Rather than accept the status of a novice and nobody in the new order, most (it seems) preferred to abandon any place in it.
 
We should doubt if Jesus meant to imply that false-professors and false-teachers were welcome at all where his program was instituted
So, can I conclude that those who are "least" are outside the kingdom?

If it's so, how can we understand it in the light of this verse:

Verily I say unto you, Among them that are born of women there hath not risen a greater than John the Baptist: notwithstanding he that is least in the kingdom of heaven is greater than he. (Matthew 11:11)
 
So, can I conclude that those who are "least" are outside the kingdom?

If it's so, how can we understand it in the light of this verse:

Verily I say unto you, Among them that are born of women there hath not risen a greater than John the Baptist: notwithstanding he that is least in the kingdom of heaven is greater than he. (Matthew 11:11)
Firstly, context dictates how we regard the use of terms. The word least, or term least jn the kingdom, does not have to mean the exact same sense in two different places.

Second, in the first instance we might hope there would be repentance and ceasing from error tending to loss of place in the kingdom. That case of least is tending to utter loss.

Whereas in the second case, least refers to station relative to another very specific man and his station; only two different covenant administrations are also brought into view for comparison.
 
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