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Alexander the Great was a historical figure in Earth history. It was later revealed, in 2269, that the immortal Flint was, in fact, the former Alexander. (TOS: "Requiem for Methuselah")

A 23rd century analogy made by James T. Kirk regarding the creation of the Human Augments, whose superior ability breed superior ambition, was compared to creating a group of Alexanders and Napoléons. (TOS: "Space Seed")

In 2268, Spock listed Alexander with Ramses, Napoléon, Caesar, Hitler and Lee Kuan as examples of Earthmen whose desire for absolute power corrupted them absolutely. (TOS: "Patterns of Force")

Later that year, Fleet Captain Garth of Izar listed Alexander with Napoléon, Caesar, Hitler, Lee Kuan, and Krotus as leaders who had failed at making the ultimate conquest. (TOS: "Whom Gods Destroy")

Flint's claim to have lived as Alexander the Great is the most problematic of his aliases, given that Alexander's childhood is well documented in Greek history, especially his tutelage by Aristotle as well as the relationship he had with his father Philip of Macedonia. Flint was either therefore exaggerating about living as Alexander or had replaced (and possibly murdered) the original Alexander at some point in his adult life, possibly during Alexander’s exile to Egypt prior to his assuming the Greek throne from his father.

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