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Ann Naffziger Answers:
In first century Palestine where Jesus was living, tax collectors were individuals who worked for Roman administrators. They were responsible for collecting taxes to support the Roman Empire, which governed Jesus’ homeland. (Think of the IRS in our day.) Some of the taxes levied on the Jewish people might have been oppressive in themselves, but sometimes it was the tax collectors who made the situation unduly difficult by collecting more than was due and pocketing the difference. We know this because at one point when John the Baptist called for repentance, he warned the tax collectors to stop collecting more than what is due (Luke 3:12-13). Other citations in scripture equate tax collectors with prostitutes and other sinners (Matthew 9:10; 11:19; 21:31) so clearly they were not well regarded.
However, tax collectors were not beyond redemption. Luke tells the story of Zacchaeus, the “vertically challenged” tax collector who had to climb a tree to get a glimpse of Jesus above the crowd. He knew he was regarded as a sinner, but he promised that if he had overcharged anyone he would repay it four times over. For this Jesus promised that salvation had come to his house (Luke 19:7-8).