16 They sent their disciples to Him along with the Herodians. “Teacher,” they said, “we know that You are honest and that You teach the way of God in accordance with the truth. You seek favor from no one, because You pay no attention to external appearance. 17 So tell us what You think: Is it lawful to pay taxes to Caesar or not?” (Matthew 22:16-17)
14 “Teacher,” they said, “we know that You are honest and seek favor from no one. Indeed, You are impartial and teach the way of God in accordance with the truth. Is it lawful to pay taxes to Caesar or not? Should we pay them or not?” (Mark 12:14)
21“Teacher,” they inquired, “we know that You speak and teach correctly. You show no partiality, but teach the way of God in accordance with the truth. 22 Is it lawful for us to pay taxes to Caesar or not?” (Luke 20:21-22)
I am of the belief that either a yes or no answer would have gotten him in trouble, If he would have said "No, you shall not pay taxes to Caesar" they would have informed the Romans that he teaches the people not to pay taxes but what if he would have said plainly "Yes, you shall pay Caesar taxes" most likely they would have found something in the Law against him, so rather then to exhort them to pay taxes he tell them to give back what belongs to Caesar.
Would it have been wrong to tell the Israelites to pay taxes to Caesar?
Are there any command against paying foreigners taxes?