At some time every older sibling has pulled this on a little brother or sister who had a nickel they wanted.
"Okay," older child offers, "let's flip for it. Heads I win, tails you lose."
The little kids agrees: "Sure!" Then when heads appears the older proclaims "Heads, I win!" Of course if tails comes up the declaration is "Tails, you lose."
At this point it suddenly dawns on the younger child that this is truly a no-win situation. Whatever way the coin lands it's going to land in their sibling's pocket.
In this week's gospel text the Pharisees think they've concocted the perfect no-win question to present before Jesus: "Is it lawful to pay taxes to the emperor, or not?" If Jesus says yes, he'll alienate all those who continued to struggle against Roman rule and who ardently believed Israel must only be obedient to God and God's Torah. If, however, Jesus answers no, then he's immediately at odds with the entire Roman Empire and has identified himself as a dangerous, seditious opponent. Rome would deal swiftly with such a threat.