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In the spring of 399 BCE, surrounded by students and friends, the Athenian philosopher Socrates was condemned to die by drinking a hemlock cup. Almost five hundred years later, in 65 AD, the Roman philosopher Seneca allegedly chose to recreate his forced suicide in the same manner as Plato’s teacher. Both men were older, both were shunned by the authorities, and both shared a passion for wisdom – but other than that, few similarities remain. Socrates was poor, known for walking barefoot around the streets of Athens, while Seneca was the second wealthiest man in the Roman Empire. Though Socrates never wrote a single line of text, Seneca was an extremely prolific writer; and while Socrates preferred to stay out of politics, Seneca was (for better or worse) part of Nero’s inner circle. The contradictions abound, yet somehow Seneca felt a connection to Socrates that was strong enough to emulate his demise. By focusing on Plato’s Phaedo and Seneca’s Consolatio ad Marciam and Letter 65, this paper seeks to explore the common elements between them, both in their ideas about death and in the philosophers’ manners of dying.