Homiletics professor and Matthew commentator Tom Long rephrases the Caesar and Tax question to Jesus like this. "In effect," he writes, the opponents of Jesus ask, "Are you a foolish, uncompromising revolutionary whose allegiance to the kingdom of heaven is actually a political revolution in disguise, or are you a smooth-talking street preacher who stirs up people with glib talk of God's majesty but who underneath advocates a get-along-go-along policy with the Roman, Gentile pigs?"
Westminster John Knox Press, Matthew, Westminster Bible Companion, by Tom Long