This is the fourth discourse of Jesus that Matthew has presented. This one takes the lesson of the Sermon on the Mount and applies it to those who will establish the church during the age of delay. In summary, it requires that the church preach the gospel for salvation and sanctification. That is, everything comes from the hand of the King, particularly imputed righteousness, and to teach otherwise (works) is to cause believers to stumble and incur the discipline of God Himself.

The question asked is who is the greatest in the kingdom. Jesus answer is that there are two categories, the greatest and the least. The greatest are all those who enter the kingdom, while the least are those who do not.

Jesus illustrates who will be in the kingdom through the use of a little child. One must be turned, or be humble to enter the kingdom. While humility by itself does not explain the ability to enter, Jesus will define that in the next verses to be that of belief in Him. Thus one believes in Him for their righteousness and is turned from their own righteousness which requires humilty.

It is important to notice that the 'greatest' is a resident of the kingdom, not necessarily indicating that this one is greater than someone else in the kingdom. He is greater with respect to the one who is outside the kingdom ('the least') in Matt. 5. The 'humble' are those who see their own depravity (lack of status with God) and ask. The 'repentance' here is a change from their understanding of their present self-'righteousness' to that of God's righteousness in Christ.