To understand the tax collectors of Jesus’ day and how they were viewed by their fellow Jews, we must first gain some insight into the tax system in Israel. At the time of Jesus, Israel was under Roman occupation, and Rome exercised its authority over Israel by placing governors over some of its provinces (e.g., the Harods in Galilee and Judea).
Rome also installed a comprehensive tax system throughout its empire to fund the local and national governments, infrastructure, public building projects, markets, stadiums, and so on. Throughout the empire, taxes were levied on property, exports and imports, the use of roads, income, crops (wine, fruit, and oil), entrances into towns, the transportation of goods, and even taxes on salt, purchases (sales tax), animals, vehicles, and the selling of slaves. (The Jews were also taxed annually for use of their temple.)
Rome eventually started to offer regional tax “franchises” to entrepreneurs who would bid for the opportunity to oversee a tax collection service in a given area. The entrepreneur would then hire local tax collectors to gather taxes from residents.
Apart from setting the required tax quota, Rome exercised little regulation over these franchises, so the Publican (a Latin term that referred to the owner of the franchise, not a local tax collector) was able to establish his own commission. By offering these franchises to the highest bidder and allowing the Publican to set his own rates, the system was vulnerable to fraud. These tax collectors were usually involved in collecting indirect taxes (tolls, customs, etc.) and were usually located at the entrance of major towns and ports of entry.
Jewish tax collectors in Israel were despised for at least two reasons. The first reason is due to their connection with a foreign power that was presently occupying Israel. For a Jew to collect money for Rome was to betray his own country and lend legitimacy to Roman occupation.
Second, tax collectors were known to be greedy, dishonest, and generally unethical in their work. The practice of overcharging and lining their pockets with the extra money was probably common, and fellow Jews viewed such a practice as double-betrayal: they were funding a foreign empire while stealing from their own countrymen. In Rabbinic literature, tax collectors were considered no better than thieves, so it was morally acceptable to defraud them in return for their unscrupulous practices.
When we come to the New Testament, therefore, we can understand why tax collectors were so detested, and why it was such a scandal for Jesus to eat with them (Luke 5:30) and go to into their homes (Luke 19:5-6). It is likely the case that Levi (Matthew) was a local tax collector who collected customs on trade routes in Capernaum (Matt 9:9; Mark 2:14; Luke 5:27). Zacchaeus, a chief tax collector, was probably a Publican who had purchased the right to tax a given area. He had apparently gained his wealth by taking advantage of the tax system and fleecing his fellow Jews (Luke 19:8).
While the religious leaders and the crowds openly despised the tax collectors and kept their distance from such rabble, Jesus ate with them and joined them in their homes (Luke 5:30; Luke 19:5-6). But Jesus didn’t condone their sin; he met with tax collectors in order to call them to repentance. Jesus did not dine with tax collectors and other flagrant sinners in order to coddle them in their rebellion against God. He spent time with them in order to turn them from their rebellion against God.
John the Baptist, Jesus’ forerunner, told repentant tax collectors that they should no longer collect more than what they are authorized to collect (Luke 3:13). Jesus even used the tax collector as an example of selfish, self-centered love (see Matt 5:46).
In other words, Christ didn’t overlook the tax collectors’ sin; it was something from which they needed to genuinely repent. Nevertheless, it is regularly the case that those who are irreligious and blatantly immoral are able to more easily recognize their need for Christ, which is why Jesus responded to the Pharisees’ self-righteous grumbling by saying, “Those who are well have no need of a physician, but those who are sick. I have not come to call the righteous, but sinners to repentance” (Luke 5:32). Jesus didn’t eat with tax collectors merely to “hang out” with them, but to call them to repentance and salvation (Luke 19:10).
Jesus’ model of evangelism, then, shows us that we must be willing to engage—with the gospel—those whom the world despises. But it also shows us that we are not called to merely spend time with flagrant sinners; nor should we engage with them in a way that condones their sinful lives or participates in their sin. Rather, we are to use these opportunities to lovingly call them to repentance.