In his robust and polarizing style, Paul makes claims that have provoked readers in numerous ways, at times spurring admirers to follow daring paths with radical implications for theology, but sometimes irritating his critics, who have raised numerous objections on theological, philosophical, and moral grounds. Paul divides opinion as much today as he did in his own lifetime. This essay discusses five topics where Paul proves to be challenging. In each case, we will trace how Paul subverts some aspects of an ancient value-system, not by a straightforward inversion of values but by his reconfiguration of what is good and necessary around the event of Christ crucified and risen. In many cases we will find that there is a partial match between Paul’s Christological configuration of values and the liberal values espoused by the majority of intellectuals in the modern West, with respect to justice, equality, freedom, and human rights. If Paul is to remain in any sense a constructive challenge, we will need to deploy a creative theological hermeneutic, which attempts to recontextualize Paul’s core insights in our own very different historical, intellectual, and social setting.