Cyril of Jerusalem

Concerning the robbers who were crucified with him it is written, "And he was numbered with the transgressors." Both of them were before this transgressors, but one was so no longer. For the one was a transgressor to the end, stubborn against salvation; who, though his hands were fastened, struck with blasphemy by his tongue. When the Jews passing by wagged their head, mocking the crucified and fulfilling what was written, "When they looked on me, they shook their head," he also reviled with them. …

Catechetical Lecture 13:30 ↗

Augustine of Hippo

Three men were crucified in the same place, the Lord in the middle, because "he was reckoned among the wicked." They placed the two robbers on either side, but they were not crucified for the same reason. They were flanking Christ as he hung there, but they were far removed from him in reality. They were crucified by their crimes, he by ours.

Sermon 285:2 ↗

Jerome

Therefore I will divide him among the many, and he will share the spoils of the strong, because he poured out his soul to death and was numbered with the transgressors. Yet he himself bore the sin of many and interceded for the transgressors. LXX: Therefore he shall receive many as his portion, and he shall divide the spoils with the mighty, because his soul was poured out to death and he was numbered with the wicked. He himself bore the sins of many and was delivered up for their iniquities. …

Commentary on Isaiah ↗

Thomas Aquinas

Therefore will I distribute. Here he sets out his victory over his enemies. And first, he sets out the subjection of the enemies: therefore will I distribute to him, as if to say: I will give him his part, very many, who will believe in him; and the spoils of the strong, that is, those held captive by demons, he shall divide, among his disciples, setting different disciples over different nations: he shall carry off the treasure of every desirable vessel (Hos 13:15); the king of powers is of the beloved, of the beloved; and the …

Commentary on Isaiah ↗