Paul's stated policy of adaptability in 1 Corinthians 9:19-23, that he seeks to "gain" those hupo nomos ("under law") as well as the anomos ("lawless," often translated "without law") by "becoming like" each different target audience when among them, has been interpreted to refer to adaptation of his conduct to that of his audiences, and thus along the same line signified in the popular cliché, "When in Rome, do as the Romans do." In this long-standing interpretive tradition, "becoming like… all people in order to gain all people" thus ostensibly signifies for Paul "conducting himself in the same way as each kind of people do when among each kind of people in order to gain every kind of people." In the case of Rome itself, would it signify, for example, eating like a Roman eats in order to evangelize among Romans? If so, would he be willing to eat pork, a favorite delicacy of Roman tables, when among Roman non-Jews? If so, this would indicate that he was not Torah-observant as a matter of covenant faithfulness, but only when evangelistically expedient, in keeping with the traditional portrait of Paul as Torah-free after his turn to faith in Christ. This paper will challenge the prevailing views of what Paul meant by the language of "becoming like" various audiences in order to "gain" them in 1 Cor 9:19-23, and specifically, that it had to do with "behaving like" them, as is usually signified in the epithet, "when in Rome, do as the Romans do."