Albert Barnes Commentary Matthew 22:15

"Then went the Pharisees, and took counsel how they might ensnare him in [his] talk." — Matthew 22:15 (ASV)

Then went the Pharisees. See Barnes on Matthew 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 into the area of the net, and then suddenly springing it over them. So, to entangle is to artfully lay a plan for enticing, to beguile by proposing a question, and by leading, if possible, to an incautious answer. This was the kind of plan proposed to Jesus here.

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 previously said.