Do you hate paying taxes? Maybe you think you pay too much. That others don’t pay enough. Maybe you don’t like what its being used for. Maybe the system is just too complicated and a hassle.
In Jesus’ day, people also hated paying taxes. As noted in a prior post, Jesus lived and ministered during the “Pax Romana”, or “Roman Peace”, which was announced by Roman Caesars in “gospel” messages telling the people they benefited from unprecedented peace and prosperity due to the godlike powers of the Caesars and their Roman government. Of course, these benefits could be expensive and had to be financed.
Worse than Turbo Tax
Enter the tax collector, or as some historians say: the tax “farmer”. Instead of collecting taxes themselves, the Roman state sometimes sold the right to collect taxes to individuals at contracted rates. Tax farmers collected required taxes, including “ground-, income-, and poll-tax. The ground-tax amounted to one-tenth of all grain and one-fifth of the wine and fruit grown; partly paid in kind, and partly commuted into money. The income-tax amounted to 1 per cent.; while the head-money, or poll-tax, was levied on all persons.”
On top of this, the tax farmer invented other taxes for his own benefit, “such as on axles, wheels, pack-animals, pedestrians, roads, highways; on admission to markets; on carriers, bridges, ships, and quays; on crossing rivers, on dams, on licenses”. These taxes the farmer would keep for themselves, usually making them incredibly wealthy.
Adding insult to injury, they sometimes would use Roman soldiers to enforce payment, or if they were especially well-off, they had their own private enforcement squads, subjecting citizens to the “vexation of being constantly stopped on the journey, having to unload all one’s pack-animals, when every bale and package was opened, and the contents tumbled about [and] private letters opened.”
Not Religious Freedom
Now enter Pontius Pilate, the Roman governor of Judea and Samaria, who later presided over the crucifixion of Jesus Christ. Pilate was the man in charge of maintaining the hypocrisy of the “Pax Romana” while the soldiers under him harassed citizens for taxes. He had a history of provoking the Jews and reminding them of their powerlessness, including seizing money from the Jewish Temple treasury to build an aqueduct, and by prominently posting Caesar propaganda within Jerusalem. Both instigations are recorded by first-century historian Josephus.
Therefore, to many Jews of Jesus’ day, tax payments were seen as not only supporting the corruption of the tax collector, but also as financing an oppressive government and its pagan gods. Often, the tax collector was Jewish himself, putting themselves forward for the job, then being appointed by their province. In them, Jewish leaders saw not only a symbol of their contempt for “Pax Romana”, but also traitors and cheaters, representatives of an enemy power. “They were a criminal race, to which Lev 20:5 applied,” which says “then I will set my face against that man and against his clan and will cut them off from among their people, him and all who follow him in whoring after Molech.” All tax collectors as a group fell under the Rabbinic ban, or their version of excommunication. Under the ban, a person or group of persons became “like one dead”, not allowed to socialize with other Jews, who could not even give them directions. “It was forbidden to eat or drink with such a one.”
Zacchaeus Has No Friends
In Luke 19, we meet one of these chief tax collectors, Zacchaeus, who appeared to be having a mid-life crisis. He was a very rich, successful man because of the abuses described above, but was trying to reform. Luke 19:8 records Zacchaeus’ words when he met Jesus: “And Zacchaeus stood and said to the Lord, ‘Behold, Lord, the half of my goods I give to the poor. And if I have defrauded anyone of anything, I restore it fourfold.’” Comically, he had to climb a sycamore tree to see Jesus at all, who was surrounded by crowds.
Excommunicated from the Jewish faith, and probably less popular with his Roman bosses due to collecting less tax, Zacchaeus was looking for anyone to accept him. We don’t know for sure what led Zacchaeus to search for Jesus, but maybe he knew about John the Baptist calling tax collectors to “Collect no more than you are authorized to do”, as recorded in Luke 3:10-13. Later, maybe Zacchaeus heard Jesus’ teaching about taxes and tax collectors as did Matthew, another tax collector and eventually author of the first book of the New Testament. In Luke 18:9-14, Jesus contrasted the obnoxious self-righteousness of a Pharisee to a humble tax collector begging for forgiveness.
When Jesus saw Zacchaeus in the tree, he called out “Zacchaeus, hurry and come down, for I must stay at your house today.” Then came the complaints of the Pharisees, a group of religious leaders, who “grumbled, ‘He has gone in to be the guest of a man who is a sinner.’” See, the Pharisees were right that Zacchaeus is a sinner. They were right that he was an oppressor. The Pharisees divided the world into “us” and “sinners”, and expected Jesus to do the same. After all, the Rabbinic ban applied to the entire class of tax collectors and if Jesus wanted to be a Rabbi, he had to enforce the ban. If they were Mandalorian, they would have said “This is the way!” 
In contrast, earlier in Luke 6:27-32, Jesus taught:
“But I say to you who hear, love your enemies, do good to those who hate you, bless those who curse you, pray for those who abuse you. To one who strikes you on the cheek, offer the other also, and from one who takes away your cloak do not withhold your tunic either. Give to everyone who begs from you, and from one who takes away your goods do not demand them back. And as you wish that others would do to you, do so to them. If you love those who love you, what benefit is that to you? For even sinners love those who love them.”
The first part of this seems to be describing precisely the actions of tax collectors and their thugs, and saying “Love them!”. The latter part sounds like a rebuke to the Pharisees. What the Pharisees did not understand is that from Jesus’ perspective, all are sinners and all are enemies of God. Fortunately, He does not leave it at that: “God shows his love for us in that while we were still sinners, Christ died for us” – Romans 5:8. If Jesus had not loved His enemies on the cross, we – including the Pharisees – would all be without hope, like Zacchaeus in the sycamore tree.
Jesus announced “Today salvation has come to this house, since he also is a son of Abraham. For the Son of Man came to seek and to save the lost” – Luke 19:9b-10. In saving Zacchaeus, Jesus was proclaiming a new paradigm, where there is no “Us versus Sinners”, but in His death and resurrection He created a church that is “Him for Them”, and then “Us for Them”. He elevated Love above “truth”, letting the Pharisees know that although their accusations against Zacchaeus and all tax collectors were “true”, that truth was not good enough. The truth of the Law condemns because we are all sinners. Jesus is the Truth we need, that brings peace and sets free. Zacchaeus was excluded from church and state, but Jesus offered a third, superior kingdom that would accept him. By disowning his sin (Luke 19:8 above), Zacchaeus didn’t become perfect, but he acknowledged Jesus as the Savior and King he needed and relied on His grace.
The Pharisees continued longing for a political messiah who would get rid of traitors like the tax collectors and overthrow Rome. Their worldview pointed back to the reign of King David, who oversaw a sovereign Jewish nation governed by the laws of the Pentateuch, with a “pure” system of Jewish law centered around worship and sacrifice at the Temple in Jerusalem.
Rather than being reformed by the Zacchaeus episode, Pharisees later tried to force Jesus to take sides between church (as the Pharisees saw it) and the occupying Roman state in Luke 20:19-25, asking “Is it lawful for us to give tribute to Caesar, or not?” Jesus deftly replied, “render to Caesar the things that are Caesar’s, and to God the things that are God’s.” Jesus did not condemn paying taxes even though he knew fraud and corruption was involved, but he earlier demanded that those responsible for corruption repent.
If you feel like a Pharisee in this story, break the stereotype of “Us vs. Them.” Find a Zacchaeus out there and bring the love and forgiveness of Jesus to them. I guarantee you know one. The nightly news or your social media feed are probably very good at identifying enemies. However, “Blessed are the peacemakers”, because they are like Jesus.
Zacchaeus probably continued to collect taxes, but as a reformed man. He would refuse to be a cog in a corrupt machine. As a chief collector, he may have influenced subordinates to be less corrupt, and therefore his conversion was good for the citizens while also making Pax Romana look more like its propaganda and less like what the Pharisees hated. A bit of the righteousness and justice of heaven was injected into Pax Romana because Jesus saw Zacchaeus as a person, and not as a category or type, beyond redemption under the ban.
If you feel like Zacchaeus in this story, cast out and rejected with unforgiving enemies on every side, turn to Jesus. Perhaps you feel like the religious establishment doesn’t like you or your kind. Jesus is not the religious or political solution the Pharisees and Romans wanted, but He is the solution – the Answer. For you.
The Right Side of History
When people say they are on “the right side of history” they’re implicitly claiming to know the future and also claiming the right to judge the present based on that knowledge. However, they often ignore the One who actually does know the future. When Jesus met Zacchaeus, saving him from slavery to the kingdom of sin was more important at that moment than overthrowing Rome and saving the Jews from state oppression. Jesus knew that Zacchaeus’ soul was eternal, but that Rome and all its institutions and culture were temporary. Only in hindsight do we know what Jesus already knew at the time: in AD 66, Rome would invade and level the city of Jerusalem, including desecrating the temple. In 410 AD, Germanic tribes would sack the city of Rome and eventually overthrow the empire of Pax Romana.
What was Zacchaeus’ fate in AD 66? We don’t know, but if we are Christians, we know we will meet him in heaven. He was rescued, spiritually, just days before Jesus went to the cross for him. Jesus overcame the temporary power of the world – the oppressing power of sin and darkness that enslaves us – by offering Himself and the radical power of forgiveness. Zacchaeus was a state oppressor of the Jews as an agent of Rome, and also religiously oppressed by the Jews who tried to keep him from God, but he will outlast both systems. He overcame, in Jesus, the Oppressor that cuts across all categories of people – sin. “There is neither Jew nor Greek, there is neither slave nor free, there is no male and female, for you are all one in Christ Jesus.” – Galatians 3:28
From the perspective of eternity, being on “the right side of history” is when the oppressor loves the oppressed and the oppressed loves the oppressor. Isaiah 11:6-9 describes the future from which Jesus will judge our present actions and whether we are on the right side:
“The wolf shall dwell with the lamb, and the leopard shall lie down with the young goat,
and the calf and the lion and the fattened calf together; and a little child shall lead them.
The cow and the bear shall graze; their young shall lie down together;
and the lion shall eat straw like the ox.
The nursing child shall play over the hole of the cobra,
and the weaned child shall put his hand on the adder’s den.
They shall not hurt or destroy in all my holy mountain;
for the earth shall be full of the knowledge of the LORD as the waters cover the sea.”
 Edersheim, Alfred. The Life and Times of Jesus the Messiah (1886). P. 357
 Josephus. The Jewish War (2.9.2) (AD 75) and Antiquities of the Jews (18.3.1) (AD 93). Cited in Wikipedia entry on Pontius Pilate.
 Edersheim, Alfred. The Life and Times of Jesus the Messiah. (1886). P. 357.
 Molech was a god of the Ammonites, whose followers sometimes sacrificed their children to him by fire. Ammonites were descendants of Abraham’s brother Lot, through his younger daughter who got him drunk and seduced him. (Gen 19:38)
 Edersheim, Alfred. The Life and Times of Jesus the Messiah. (1886). P. 602.
 Possibly referring to Exodus 22:1 – “If a man steals an ox or a sheep, and kills it or sells it, he shall repay five oxen for an ox, and four sheep for a sheep.”
 Luke 19:5
 In the Disney+ series, The Mandalorian, the title refers to a tribe of bounty hunters who use this phrase when referencing their shared code of conduct.
 The first 5 books of the Bible, or the “books of Moses”
 Matthew 5:9
 See my first post, “42 is Not the Answer” for more on how Jesus is the Answer.