Here’s the thing, the Pharisees often accused Jesus of hanging around with tax collectors and sinners (Matthew 9:10-11, Matthew 11:19, Mark 2:15, Luke 5:30, Luke 7:34). However, when Jesus himself talks about Tax collectors and sinners, he actually uses the words tax collectors and prostitutes (Matthew 12:32-33). This suggests that the Pharisees were using the word sinners as a euphemism for prostitutes. A bit like the terms lady of the night or fallen woman. If so, then Jesus was indeed hanging around with some of the most despised men and women of Israel. The strength of this assumption is confirmed by the massive reaction of the Pharisees when Jesus’ feet were anointed by a woman of the city, who was a sinner while having dinner at a Pharisees home (Luke 7:36-50).

There’d always been prostitutes in ancient Israel, but not nearly on the scale of the pagan cultures surrounding them where slave women were often thrown into prostitution as a form of profit for their owners, and many of their temples were also full of cult prostitutes. However, at this particular time in Jewish history prostitutes were thick on the ground in Israel, but why?

Jewish women came to this degrading “profession” for several traditional reasons and one very new reason:

First, a poor woman who lost her husband would sometimes have no choice but to start selling her body. The only ancient welfare system for women and children was the family, and if that was gone due to war or famine, then a woman was on her own. I know a man who lived Kazakhstan just after the fall of Communism and he said prostitution was endemic as people had lost their welfare system, were poor and desperate for any form of income.

Second, if a Jewish marriage was childless then the woman was always blamed and would sometimes be rejected by her husband and his family, driving her to desperate measures. This still often happens in developing countries where children are considered a prime reason for marriage and needed for the farm or small business. The woman at the well in John 4 was probably in this situation. She had had five husbands and a boyfriend, with no children mentioned. She must have been terribly rejected by her village because of her so-called curse, hence her appearance at the well during the middle of the day.

Third is the elephant in the room, the Roman invasion in 63BC. With it came thousands of young testosterone-fueled men who were banned from raping local women and from marrying them as well. This created a huge new demand for paid prostitutes. Jewish society was quickly corrupted on a scale not seen before. Polite Jewish society was shocked at this rapid downhill decline in social standards. No religious rabbi would therefore be seen dead with this new underclass. They were rejecting Gods laws and standards so deserved to be rejected.

tax collectors and prostitutes were always lumped together in scripture because as Jewish tax collectors were hanging around the Romans a lot for business purposes, they became somewhat Romanised. The Roman banquets they attended usually included prostitutes for the after-dinner “entertainment” and the tax collectors must have taken on this culture as the term tax collector and sinner/prostitute became inseparable. The woman who broke her alabaster perfume bottle over Jesus’ feet had met him was most likely one of these women (Matthew 26:6-7).

Now the big question is why did Jesus, God in human form, Immanuel, the lamb of God who took away the sins of the world, the pure and righteous son of the creator of the universe, hang around with tax collectors and prostitutes? Surely he could target better people to launch a global spiritual transformation! However, Jesus was an astute sociologist as well as a spiritual doctor. In Matthew 9:12-13 he said, it is not the healthy who need a doctor but the sick…For I have not come to call the righteous, but sinners.

Jesus also knew the rank hypocrisy of the upper-class religious leaders toward tax collectors and prostitutes. The story of the prodigal son (Luke 15:11-32), the parables of the lost coin, and lost sheep (Luke 15:3-10), the story of the two debtors (Luke 7:41-50), and the story of two men going up to the temple (Matthew 21:28-33) were all told in response to accusations of Jesus hanging around with the wrong crowd and being one with them. Jesus needed to constantly expose their hypocrisy. The woman caught in adultery also emphasized the hypocrisy of condemnation of the elite toward those whose sin is open as compared to their own hidden sin. She was not condemned but also told not to continue in her ways.

At the start of his ministry Jesus said he came to proclaim freedom for the prisoners and to set the oppressed free (Luke 4:18-19). His mission was redemption, not religion or rules. He came to set the human heart free to commune with our loving heavenly father and you can’t do that from a distance, you can’t do it by hanging around with the nice people. He didn’t condone prostitution but knew most of those involved in it were full of shame, self-loathing and guilt, that they hated what they were doing and were being abused relentlessly. They needed grace not judgement. The heart of compassion wants to help set people like this free. If a broken prostitute could be brought back into relationship with the Father of Lights, then any human could be. This was a radical shift in human understanding of the divine.

This is why the woman with the bottle of perfume was full of tears. She knew she was finally free from sin because of no one else but Jesus (Luke 7:36-49). A friend of mine once ran a shelter for prostitutes in India. One lady they rescued had been sold by her uncle into this most abusive of lifestyles. After she had been finally rescued and heard that she was loved by God despite what she had been through she cried out of relief for three days and nights straight! Now can you appreciate the power of those tears at the feet of Jesus!

To learn a whole lot more about the sheer horror of prostitution and the massive toll it takes on the lives of those unfortunate enough to be caught up in its satanic claws please read this story from the BBC about Brenda Myers who was trapped in prostitution for 25 years from the age of 14. She was shot five times, stabbed thirteen times and beaten senseless too many times to remember…until the day she called out to God for help.