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;
All Commentaries on 1 Corinthians 9:20 Go To 1 Corinthians 9
Ambrosiaster
AD 400
Did Paul merely pretend to be all things to all men, in the way that flatterers do? No. He was a man of God and a doctor of the spirit who could diagnose every pain, and with great diligence he tended them and sympathized with them all. We all have something or other in common with everyone. This empathy is what Paul embodied in dealing with each particular person. Commentary on Paul’s Epistles.