A few questions....
In order for a minister (doctor so to speak) to reach the sinners, will he not have to associate with them but not partake in their sins? I believe so.
And, secondly, was not the message of Jesus (and John the Baptist) to repent of sin? I believe so and that that was his message while he was hanging out with them.
Thirdly, can it not be reasonably assumed that those so called "sinners" who continued to follow Jesus about do so because they either were experiencing the joy, peace, and freedom of repenting of their sins, or they were still trying to clear the sinful hurdle in their lives and were seeking the way?
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Granted, I have little doubt that many of the 'sinners' who were following Jesus sometimes slipped back into sin due to weakness of the flesh as many Christians of today and yesterday have done, and as many of the Jewish peoples of the Old Testament accounts have done. This said, yes Jesus was among sinners...
But, I ask this...... "Where on EARTH could Jesus have gone to be in the presence of non-sinners?" The temple? No. The market place? No. His hometown? No.
Jesus' actions were simple. Announce the kingdom of Heaven is near and REPENT. Why to prostitutes and drunkards? Because they were not blind in hypocracy like the Pharasees in the temple.... The prostitutes and drunkards understood the law and at least knew they were in sin -- Many leaders of the religion would not recognize or acknowledge their sins,,, nor repent. Jesus showed compassion by reaching to those who at least acknowledged the sin in their lives and he did not turn away from them like the uncompassionate, blind temple leaders who sat in Moses' seat. Although Jesus did preach to the temple leaders, they would not accept his message.... The 'sinners' did accept his message and, as such, Jesus stayed among them...
And besides, in another light, Jesus was merely doing the work that the temple leaders had failed to do! Reach out to the sinners and call them to repent...... The leaders of the temple, who sat in Moses' seat, do what many Christian leaders do today --- they waited for the 'sinners' to come to them at the temple and other 'holy' sites, rather than they going to the sinners.
In the end, in the eyes of God, we are all sinners!
And, in the eyes of God, we all need to acknowledge our sins and repent.