Asoka, the third Emperor of the Indian Mauryan Dynasty, was once a violent, acquisitive ruler. After spearheading an exceptionally bloody battle, he experienced a tremendous transformation. Leaving his brutal past behind him, Asoka reverted to a life of compassion and peace. As he promoted Buddhist principles, his own transformation led to the transformation of his many followers. Asoka became a magnanimous historical leader who is recognized for Buddhism's transition from a sect to a world religion. Paul, the Apostle, too, is acknowledged for his effective evangelization of his beliefs. He is known by many as the second founder of Christianity, by others as the actual founder. Paul's Christianity was a result of a profound personal transformation that was experienced on the road to Damascus, Syria. At that time referred to as Saul, he was intent on destroying Christianity until he witnessed a vision that convinced him to convert. This conversion catalysed the transformation of followers throughout the Roman Empire and beyond, resulting in Christianity becoming a world religion. By examining the pair's actions before and after their personal transformations, as well as the subsequent results, applicability to contemporary leadership is gleaned.