ESV - 15 And as he reclined at table in his house, many tax collectors and sinners were reclining with Jesus and his disciples, for there were many who followed him.
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For this question, Jesus himself answered it in Matthew 9:1-13: When the Pharisees saw this, they asked his disciples, “Why does your teacher eat with tax collectors and sinners?” On hearing this, Jesus said, “It is not the healthy who need a doctor, but the sick. But go and learn what this means: ‘I desire mercy, not sacrifice.’ For I have not come to call the righteous, but sinners.” You can clearly extract the answer for this. Jesus stayed and ate with sinners because he came to the world for the lost. He wants to teach and preach to them, and lead them in the righteous ways. And as he clearly stated, the sick are the ones who need doctors, not the healthy ones. I hope that you have got your desired answers and that you have satisfaction.
As Jesus Himself said in Luke 5:32, "Those who are well have no need of a physician, but those who are sick. I came to call not the righteous, but sinners, to repentance." All humans are spiritually "sick" with the mortal disease of sin. The "disreputable" people with whom Jesus associated, and to whom He ministered, realized their spiritual "illness", and their need for the forgiveness and salvation that could be gained only through faith in Him. By contrast, those who condemned Jesus for the company he kept considered themselves completely righteous, and were blind to the fact of their own sinfulness and need for that same forgiveness.
In addition to the other good answers here, I would just like to add that Jesus did NOT associate with 'active sinners,' nor did He engage with them in their sins, encourage them in those evil practices or even 'tolerate' them as some choose to believe. After each time Jesus healed someone, with only a few exceptions, He said something similar to this: “Behold, you have become well; do not sin anymore, so that nothing worse happens to you.” (John 5:14). Jesus was not being accused of sinning or encouraging sin directly, He was being accused of 'guilt by association.' In the Lord's day and culture, the religious leaders stigmatized entire families and lineages for the actions of individual members. So even if your grandfather was ever caught 'publicly drunk,' (even once), your entire family became known as 'the drunks.' Nothing you did or didn't do after that mattered. Anyone associating with you was warned three times and then included as 'drunks' too! Jesus intentionally associated with these 'outcasts' because He believed that it was wrong to treat them this way. While people who are ostracized by their society may well 'succumb' to this public identity with similar behavior out of frustration or anger, Jesus would not have reinforced this decision by associating with them while they were actively sinning. However, if they took any steps at all to address the sin and simply wanted to learn from Him, He would gladly forgive the past transgressions and encourage the new behavior as well as the seeking of the kingdom of GOD and its righteousness. By doing this, Jesus drew the clear lines of GOD's ethics and morality while also providing society itself with clear examples of people actually escaping from their various social stigmas with His direct help and compassion, thereby encouraging many others to follow suit who otherwise would have no hope of 'escape' themselves.
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