Pastor Ken Wilson from the Ann Arbor, Michigan, Vineyard gets it …
How did we, the friends of the friend of sinners get to this place? Jesus was known as the friend of sinners. He took a lot of guff for being the friend of sinners. These “sinners” were a social class, not simply a theological category. They were people on the outside of Israel’s accepted circle for a host of reasons. They were not mobsters or murderers or notorious offenders. (You notice that “tax collectors” and “prostitutes” were often given a distinct designation alongside “sinners” in the gospels.) Jesus so identified with “sinners” as to bring upon himself the judgment of the religiously self-righteous. He expects us to be the friend of sinners, which means our righteousness has to exceed that of the Pharisees; it has to be a righteousness of pure sermon-on-the-mount love, not a righteousness that depends on harsh condemnations and judgment of others–the “business as usual” approach to sinners. We need to get our gentle back.