Augustine of Hippo

As we see Christians called to the heavenly feast, where is the bread of righteousness, the drink of wisdom; so we see the Jews in reprobation. The children of the kingdom shall be cast into outer darkness, that is, the Jews, who have received the Law, who observe the types of all things that were to be, yet did not acknowledge the realities when present.

Catena Aurea by Aquinas ↗

Jerome

But the sons of the kingdom shall be cast out into outer darkness. The sons of the kingdom signify the Jews, over whom God reigned before. They shall be cast out into outer darkness. Darkness is always within, not without. But because he who is expelled from the Lord leaves behind the light, therefore outer darkness is so named. There will be weeping and gnashing of teeth. …

Commentary on Matthew ↗

Gregory the Dialogist

Now it happened that both died. The rich man, who was clothed in purple and fine linen, was buried in hell; but Lazarus was led by angels into Abraham's bosom. What does Abraham's bosom signify but the secret rest of the fathers? Of which the Truth says: "Many will come from the East and the West, and will recline with Abraham and Isaac and Jacob in the kingdom of heaven; but the children of the kingdom will be cast out into outer darkness." For he who is said to have been clothed in purple and fine linen is rightly called a child of …

Forty Gospel Homilies, Homily 40 ↗