John Chrysostom

Observe the exceeding iniquity of Judas, that he both sets out by himself, and that he does this for gain. It follows, And he went his way, and communed with the chief priests and captains.

Catena Aurea by Aquinas ↗

Theophylact of Ohrid

By "captains" he here means the overseers of the temple buildings, or the supervisors of good order. For the Romans had appointed certain overseers over the people, so that they would not revolt, for they were rebellious. These are the ones he calls captains (in Church Slavonic — "voevody," i.e., military commanders). Or perhaps the military commanders were those who, belonging to the priestly order, held military positions. For, suffering from a love of preeminence, they involved themselves in such offices as well. …

Commentary on Luke ↗

Bonaventure

Fourth, as regards the greed of Judas the traitor, it is added: And he went and spoke with the chief priests and magistrates. He spoke with them because he knew that they thirsted for the blood of Christ. — He spoke words of betrayal, and therefore it adds: How he might betray him to them: in which conversation indeed he asked the price of blood, according to that passage in Matthew twenty-six: "What will you give me, and I will deliver him to you?" Whence the thirst of greed moved Judas, and the thirst of cruelty moved the chief …

Commentary on Luke, Chapter 22 ↗