The objective of this article is to analyse the life, concepts and writings of Lucius Annaeus Seneca, famous Roman writer and politician and on the other hand, those of the renowned Christian bishop Aurelius Augustus, also known as the historical Saint Augustine. Though parted by a period of 400 years and many generations, we can find similarities in their suffering, their ideals, the victories and failures experienced during their lifetime. The same can be determined considering the unexpected differences that arise from two admirable men gifted with wonderful rhetorical skills and the magnificent ability to write and express their concepts and reflections in their writings. Much can be said about these two historical figures and even more remains to be told, much can be discovered and even more stays hidden from sight; this is the eternal mystery of history.