Cyrill of Alexandria
However, they did not even entertain these thoughts; how could they? They approached Him, trying to provoke Him, and concealed their treacherous intentions while speaking to Him with kind words, much like ravenous beasts disguised in sheep’s clothing. The prophet David likewise condemned such individuals, saying, ‘Their words are smoother than oil, and yet they are the points of spears.’ Additionally, he stated, ‘Their tongue pierces like the point of a spear; the words of their mouth are deceitful: he speaks peaceably to his neighbor, but in his heart is enmity.’
What are they inquiring? Rabbi! We recognize that You speak and teach truthfully, imparting the way of God without favoritism. Is it permissible for us to pay taxes to Caesar or not? (Luke 20:21). How detestable is their deceit! Even though the Almighty longs for Israel to be liberated from human oppression, they fell under the authority of their rulers because they violated God’s law, completely ignoring the commandment given to them and pursuing their own desires. Consequently, they were subjected to the authority of those in power, who enforced tributes, taxes, and the burden of unfamiliar servitude. The prophet Jeremiah, who mourned for Jerusalem, voiced this plight by saying, How lonely sits the populous city, the ruler of nations has become a tribute (Lamentations 1:1, LXX). Thus, the Evangelist indicates that they attempted to trap Him in the hands of the governing authorities (Luke 20:20), anticipating that He would unambiguously declare that it was unlawful to pay taxes to Caesar (Luke 20:22).