They resorted to all means necessary to achieve their ends, even allying with their rivals, the Herodians, supporters of Herod Antipas, the ruler of Galilee. The Herodians, closely aligned with the Sadducees, formed a faction that was keen to maintain friendly ties with the Roman government, even at the expense of cherished popular beliefs. Since the Sadducees were not particularly committed to these beliefs either, the Herodians considered them as allies in their endeavors, earning the Pharisees’ scorn.
The Pharisees, the staunch defenders of the law and national identity, detested the changes permitted by the Sadducees and their followers. Yet, they resolved to partner with those they loathed to leverage their influence against the Lord. They sent their disciples to approach the Divine Master alongside the Herodians, feigning pious simplicity and sincerity to pose a question that had yet to be resolved adequately by anyone. This inquiry was timely and carried significant potential for danger. The Jews, stripped of their autonomy, were compelled to pay taxes to the Romans, a situation they found unacceptable. The populace, led by the Pharisees, believed that taxes owed to foreign powers were contrary to the spirit of the Mosaic law, asserting that only those necessary for worship were obligatory for a true Israelite. Meanwhile, Herod's followers and some Sadducees, driven by necessity, deemed it lawful to pay tributes to an occupying government.
Using a guise of respect, the cunning schemers approached the Savior and said, “Teacher, we know that thou art true, that thou speakest rightly, and teachest truly the way of God, and caredst not for any man, for thou seest not the face of man. Surely you will not say anything to please Pilate or Herod, nor will you be afraid of Caesar himself,” - but tell us: what do you think? - Shall we pay tribute to Caesar, or not? What deceit lies in their inquiry!
St. John Chrysostom notes that they do not ask for what is good or useful, or in accordance with the law, but merely what He thinks. Their intent was solely to entrap Him and frame Him as opposed to the highest authority. The flattery in their approach suggests they anticipated a negative response, believing that the Messiah would not wish to discourage the hopeful aspirations of a people yearning for liberation from foreign oppression. Despite the teachings about a heavenly and spiritual kingdom, the people expected tangible earthly benefits from the Messiah, particularly the restoration of independence. A negative response in the presence of the Herodians would provide the Pharisees with a critical opportunity to accuse the Savior before the Roman governor: they would not hesitate to paint Him as a dangerous opponent of Roman authority, a disruptor of public peace, making it harder for the people to adjust to their foreign rule. They would rush to inform Pilate, Herod, and even reach out to Rome, declaring, "This Man says that there is no need to pay taxes to you. You protect us from robbers, construct bridges, roads, palaces, and what does He say?" They would waste no time in bringing Him to judgment.
However, even if the Lord had answered affirmatively, the Pharisees would not have felt defeated. They could argue that He harbored no affection for the Jewish people, desiring them to remain in bondage and work tirelessly to give a large portion of their earnings to their conquerors. The people, hearing the revered Teacher openly acknowledge Roman authority and endorse a legal tax to foreigners, would be justifiably outraged, potentially leading them to rebellion—an outcome desired by the enemies of Christ. Ultimately, had the Savior chosen to remain silent in the face of their malicious query, the Pharisees could have exploited His silence to diminish His prophetic stature in the eyes of the people.