Sunday’s Gospel readings shows two opposing parties (Herodians and Pharisees) working together, to set Jesus up. The Herodians supported Roman rule and the Herod family (the local kings backed by Rome). The Pharisees were scholars of the law, and popular with the people as nationalists opposed to Roman occupation.
Here’s the "lose-lose" that the trick question tries to set up. If Jesus answers against paying the tax, the Herodians will charge him with treason. If Jesus answers for paying the tax, the Pharisees will denounce him to the people as a Roman collaborator.
Sometimes in political campaigns, candidates get so wrapped up in telling people what they want to hear that they make conflicting claims and promises to different groups. If their opponent is paying attention, they will get called out for waffling or pandering.
Make no mistake, Jesus isn't waffling and his response is anything but pandering. But if it isn't waffling or pandering, what is it? More on this tomorrow.