I feel like there's some balance between "Jesus hung out with sinners" and "Jesus ONLY hung out with sinners so He could tell them to repent", but I'm not sure what it is
In the beginning of the gospels Jesus is depicted as being tempted by the devil for 40 days and 40 nights while he was living in the wilderness among the wild beasts.
This means that Jesus was living outside of the jurisdiction of Jewish law, the wilderness, (roman towns and villages), among the "wild beasts" meaning the romans, presumably doing what romans do.
According to scripture Jesus partied and hung out with sinners, prostitutes, tax gatherers, and kept all sorts of bad company, the equivalent of first century mobsters, the wild beasts.
When the Pharisees asked Jesus why he upbraided them who always tried to be righteous he told them that only the sick need a doctor, meaning that they, the Pharisees, were the sick ones, not the people that he chose as friends to hangout with. They were demonized, marginalized, criminalized and hated consequent to the perpetuation of perverse interpretations of Mosaic law, the same exact perverse interpretations of Mosaic Law perpetuated by all Christian churches.
If you have ears to hear then hear.
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