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"When I was with the Jews, I lived like a Jew to bring the Jews to Christ. When I was with those who follow the Jewish law, I too lived under that law. Even though I am not subject to the law, I did this so I could bring to Christ those who are under the law. When I am with the Gentiles who do not follow the Jewish law, I too live apart from that law so I can bring them to Christ. But I do not ignore the law of God; I obey the law of Christ. When I am with those who are weak, I share their weakness, for I want to bring the weak to Christ. Yes, I try to find common ground with everyone, doing everything I can to save some. I do everything to spread the Good News" (1 Cor. 9:20-23).
Paul was a free Roman Citizen, but he was willing to become a slave to all so that he might win them to Jesus. He was under grace not law, but when he was amongst the Jews he followed Jewish customs, obeyed the law and conformed to Jewish practices. He didn't want to needlessly antagonize his own people.
When he was living alongside non-Jews, he fitted into their way of life. He kept the moral law and obeyed the teachings of Jesus, but didn't worry about Jewish religious rituals and practices. He left his own culture behind and embraced that of those he was trying to reach. He honoured their culture as much as possible without compromising his commitment to Jesus.
Paul didn't ignore the weak, the vulnerable and marginalized, but rather he empathized with them, found common ground, shared their weakness and sought to point them to Jesus. It is not clear precisely to whom Paul was referring, but the Greek word translated "weak" means "those who are literally not strong; they might be physically, morally or spiritually weak; infirm or sick; or simply without strength". I had thought that Paul was referring to those weak in faith, but in this context that cannot be the case. He had just talked about winning the Jew and winning the Gentiles and here he is talking about winning the weak. Let's not forget that Jesus is the friend of sinners. I am certain Paul was too.