The Roman tax system was divided into districts. Each district was required to collect the assigned tax imposed by Rome. This tax booth was located in a region ruled by Herod Antipas, Tetrarch of Galilee. This means that Levi or Matthew was an employee of Herod Antipas. The Roman system allowed individuals to bid for the right to collect taxes. The highest bidder won the right to collect taxes. Luke 19:2 tells us that Zaccheus was a chief tax collector. That is, he must have been a high bidder for his area. In turn, he could then employ others to help him collect his promised taxes.

Two types of taxes were collected: fixed and duties or tolls. The fixed taxes were ten percent for food products such as oil, grain, and wine, as well as a one percent income tax. The duties and tolls included taxes for use of the roads, docking boats at the harbor, import and export taxes, and sales taxes. There was also a cart tax. The cart tax depended upon the number of wheels and the type of wheels used on the cart. There was no limit to the amount of money the chief tax collector or his employees could actually collect. Rome did not care how much the tax collector actually collected as long as he fulfilled his promise. If they collected more than the required bid, then they could keep the excess.

The Jewish Talmud describes tax collectors as “robbers” (Sanhedrin 25b). The Jewish Mishnah Tohorot 7:6 said that if a tax collector entered a Jewish home, it would become unclean. Gabinus, the proconsul of Syria, accused Cicero of graft in the collection of taxes. In short, tax collectors were dishonest and hated. Jewish tax collectors were despised by the Jews. They were considered to be traitors. Reportedly, they were sometimes aligned with the mob and sometimes employed “enforcers.” The gospels record that the Jews sometimes grouped them together with “swindlers, unjust, adulterers” (Luke 18:11), prostitutes (Matt. 21:32), and Gentiles (Matt. 18:17). Tax collectors were not allowed to serve as witnesses in a court because they were considered to be dishonest. They were not permitted inside the synagogues. Because of their occupation and dishonesty, they were among the richest men in society.