Paul circumcised Timothy to remove a cultural stumbling block for evangelizing Jews, but he refused to circumcise Titus because false teachers were demanding it as necessary for salvation. The key difference was the motive and context. One act was done to aid ministry, the other was rejected to defend the gospel.
“Then he came to Derbe and Lystra. And behold, a certain disciple was there, named Timothy… Paul wanted to have him go on with him. And he took him and circumcised him because of the Jews who were in that region…”
(Acts 16:1–3)
Timothy’s mother was Jewish and his father was Greek. According to Jewish law, he was considered Jewish, but uncircumcised. Paul, desiring to preach in synagogues, circumcised Timothy, not as a requirement for salvation, but to avoid offense and open doors for the gospel among Jews.
Contrast that with Titus:
“Yet not even Titus who was with me, being a Greek, was compelled to be circumcised.”
(Galatians 2:3)
Titus was a Gentile. The issue in Galatia was not cultural sensitivity but false teaching. Judaizers claimed Gentiles must be circumcised to be saved. Paul would not allow circumcision in this case because it would compromise the truth of the gospel:
“To whom we did not yield submission even for an hour, that the truth of the gospel might continue with you.”
(Galatians 2:5)
Paul was not inconsistent. He adapted where it helped evangelism (1 Corinthians 9:20), but he resisted any distortion of salvation by grace. With Timothy, it was a matter of strategic ministry. With Titus, it was a matter of doctrinal integrity.
These two cases teach that Christian liberty must be governed by love and truth, never surrendering to legalism, but also never using liberty to hinder the gospel.