Whosoever therefore shall break one of these least commandments, and shall teach men so, he shall be called the least in the kingdom of heaven: but whosoever shall do and teach them, the same shall be called great in the kingdom of heaven.
All Commentaries on Matthew 5:19 Go To Matthew 5
John Chrysostom
AD 407
For what reason then does he call some of these commandments “least,” though they are so magnificent and lofty? Jesus spoke this way because he was about to introduce his own teaching as a new law. As he humbles himself and speaks of himself with great modesty, so he refers to his own teaching in the same manner. In this way Jesus teaches us to practice humility in everything. And besides, since some suspected his teaching to be a new departure, he temporarily taught it in a more reserved way. But when you hear “least in the kingdom of heaven,” you are to think of nothing but hell and punishment. For it was his practice to speak not only of the joy the kingdom brings but also of the time of the resurrection and the fearful event of the second coming. Think of one who calls a brother a fool. That one transgresses only one commandment, maybe even the slightest one, and falls into hell. Compare that one with another who breaks all the commandments and instigates others to break them. Do both have the same relation to the kingdom? This is not the argument Jesus is making. Rather, he means that one who transgresses only one of the commands will on the final day be the least—that is, cast out—and last, and will fall into hell. The Gospel of Matthew, Homily