Paul wrote multiple times that in his view circumcision was of no value. But he gets Timothy circumcised before they go on a missionary journey. The reason is “because of the Jews”. We know that Paul would generally start preaching in the synagogue and then, when kicked out, preach to the Gentlies.
So why circumcize Timothy now?
Acts 15:36-16:5
15:36 After some days Paul said to Barnabas, “Come, let us return and visit the believers in every city where we proclaimed the word of the Lord and see how they are doing.” 37 Barnabas wanted to take with them John called Mark. 38 But Paul decided not to take with them one who had deserted them in Pamphylia and had not accompanied them in the work. 39 The disagreement became so sharp that they parted company; Barnabas took Mark with him and sailed away to Cyprus. 40 But Paul chose Silas and set out, the believers commending him to the grace of the Lord. 41He went through Syria and Cilicia, strengthening the churches.
16:1 Paul went on also to Derbe and to Lystra, where there was a disciple named Timothy, the son of a Jewish woman who was a believer; but his father was a Greek. 2 He was well spoken of by the believers in Lystra and Iconium. 3 Paul wanted Timothy to accompany him; and he took him and had him circumcised because of the Jews who were in those places, for they all knew that his father was a Greek. 4 As they went from town to town, they delivered to them for observance the decisions that had been reached by the apostles and elders who were in Jerusalem. 5 So the churches were strengthened in the faith and increased in numbers daily.
In Jewish law one is a member of the Tribe of Isreal if your mother is a Jew. Although your earthly inheritance comes from your father, your spirtual inheritence is from the mother: you are born a Jew and it is then the duty of your father to raise you as a Jew. Timothy was a known half-breed. If he was going to go into the synagogue he would be called out as he was uncircumcised and therefore apostate from the Jewish faith of his ancestors.
So Paul was being a pragmatist. While preaching circumcision was unncessary, he told Timothy to do the politic thing.
Which brings me to the application of today. Paul was not God. None of the apostles were. God worked in them despite their flaws and errors. We cannot ignore the message of Christ because it comes from those who are imperfect, for we all are imperfect.
It does not matter if Paul was pragmatic. If he was being hypocritical here. What mattered is that he could proclaim the gospel.