Albert Barnes on Matthew 22:15

Then went the Pharisees. Mt 3:7.

How they might entangle him. To entangle means to ensnare, as birds are taken by a net. This is done secretly, by leading them within the compass of the net, and then suddenly springing it over them. So to entangle is artfully to lay a plan for enticing, to beguile by proposing a question, and by leading, if possible, to am incautious answer. This was the kind proposed here to Jesus.

In his talk. The word his is supplied here by the translators, perhaps improperly. It means in conversation, or by talking with him; not alluding to anything he had before said.

(y) "Then went" Mk 12:13, Lk 20:20