Least in the Kingdom of Heaven?

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Q. Are Mt 5:19 & 11:11 talking about different kinds of people? Who is the least in the Kingdom? What are these least commandments?

A. The kingdom of God or heaven is not a physical kingdom, but the rule of God on earth:
Lk 17:21 the kingdom of God is in your midst.
Those in the kingdom are the kingdom’s subjects.

Both Mt 5:19 & 11:11 refer to the least in the kingdom i.e. the lowest rank within the kingdom, and are talking about the same kind of people:
Mt 5:19 Whoever then annuls one of the least of these commandments, and teaches others to do the same, shall be called least in the kingdom of heaven; but whoever keeps and teaches them, he shall be called great in the kingdom of heaven.
• Mt 11:11 Truly I say to you, among those born of women there has not arisen anyone greater than John the Baptist! Yet the one who is least in the kingdom of heaven is greater than he. (Also Lk 7:28)

The least in the kingdom of heaven are those who:
• annuls one of the least of the commandments, &
• teaches others to do the same.
“Annuls” translates the Greek verb “lyo” and literally means “loosens” or “relaxes”. It does not mean “breaks”, in which case the perpetrator would be transgressing the law and become a “sinner”, which would disqualify him from the kingdom. It means he complies with the commandment, but not fully, barely meeting the minimum requirements.

Which are the least commandments? The Bible did not say, but note:
Mt 23:23 Woe to you, scribes and Pharisees, hypocrites! For you tithe mint and dill and cummin, and have neglected the weightier provisions of the law: justice and mercy and faithfulness; but these are the things you should have done without neglecting the others.
The weightier provisions of the law, or the more important commandments, are justice, mercy, and faithfulness. In comparison, tithing, ceremonial cleansing (Mt 23:25-26), outward appearance (Mt 23:27-28) are lesser matters of the law. Whether they are the least, the Bible did not specify.

Lastly, we can also get some clues from the converse:
Mt 18:1 At that time the disciples came to Jesus and said, “Who then is greatest in the kingdom of heaven?”
• Mt 18:4 Whoever then humbles himself as this child, he is the greatest in the kingdom of heaven.

The opposite of “the least” is “the greatest” in the kingdom. Who are the greatest? They are the ones who humble themselves like a child:
Mt 23:12 Whoever exalts himself shall be humbled; and whoever humbles himself shall be exalted.
• Lk 14:11 For everyone who exalts himself will be humbled, and he who humbles himself will be exalted. (Also Lk 18:14)
• Jas 4:10 Humble yourselves in the presence of the Lord, and He will exalt you.

They are greatest because God exalts them. The value system in God’s kingdom is upside-down from the world’s!