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1 Corinthians 9:20
ESV To the Jews I became as a Jew, in order to win Jews. To those under the law I became as one under the law (though not being myself under the law) that I might win those under the law.
NIV To the Jews I became like a Jew, to win the Jews. To those under the law I became like one under the law (though I myself am not under the law), so as to win those under the law.
NASB To the Jews I became as a Jew, so that I might gain Jews; to those who are under the Law, I became as one under the Law, though not being under the Law myself, so that I might gain those who are under the Law;
CSB To the Jews I became like a Jew, to win Jews; to those under the law, like one under the law--though I myself am not under the law--to win those under the law.
NLT 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.
KJV And unto the Jews I became as a Jew, that I might gain the Jews; to them that are under the law, as under the law, that I might gain them that are under the law;

What does 1 Corinthians 9:20 mean?

Paul had written in the previous verse that he had made himself a slave to all people in the hopes of winning more of them. By "winning," he meant winning them to faith in Christ. Now he begins to describe in what sense he voluntarily puts himself under the authority of others.

As a preacher of Christ, Paul would become as a Jew to the Jews, and as one under the law of Moses to those under Jewish religious law. Paul was Jewish and had lived much of his life as a "Hebrew of Hebrews" under the law (Philippians 3:5). After being converted to faith in Christ, he had been freed from obligation to the law (Romans 10:4) and had preached that the same was true for all who received God's gift of grace in Christ. In doing so, he had become the target of persecution and attempted murder by the Jewish religious leaders.

That leads one to wonder what Paul meant that he became as a Jew and one under the law in order to win others to Christ. It does not mean Paul pretended it was necessary to follow the law to be saved. Nor does it mean he "acted more Jewish" when with Jewish people.

Rather, Paul continued to participate in the worship of God in Jewish synagogues while preaching Christ there (Acts 17:2–3). He continued to voluntarily submit to some Jewish customs and traditions, including the fulfillment of a Nazarite vow (Acts 21:23–26), and even receiving punishment from the Jewish leaders for preaching Christ (2 Corinthians 11:24). He did this without ever altering the gospel message that faith in Christ is the only way to be right with God.

Paul could have opted out of any participation with the Jewish religious system. He was free from all of it. Instead, he chose to remain involved, without ever compromising the message of Jesus, in hopes of winning some Jewish law followers to faith in Christ. In order to put as few barriers as possible between others and Christ, Paul was willing to sacrifice his own "rights" and freedoms.
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