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Polycrates was the tyrant of the island city-state of Samos during the mid to late 6th century BCE. "Tyrant" here being the ancient Greek term which was more of a neutral title than how the word is used in English today. By most accounts, the reign of Polycrates was actually an extremely prosperous time for Samos. He first came to power sometime after 540 BCE, when he and his brothers, Patagnotos and Syloson, usurped the throne from Aeaces, who was likely their father, during a festival dedicated to Hera. While initially power was split evenly between the three brothers, Polycrates gave a big middle finger to that situation. He had Patagnotos put to death, and Syloson fled, not wanting to stick his own neck out. Thus, Polycrates became the absolute ruler of the island, and he got to work turning his little corner of the Aegean into an incredibly wealthy superpower. He stocked up a fleet of triremes that gave Samos a naval dominance which would only be overshadowed by Athens later in history. This reinforced Samos's excellent position along important trade routes, thus earning them those big bucks. Hence why Samos was able to tout such famous names among their natives like Pythagoras and the Halicarnassus-born Herodotus.

Polycrates was also a shrewd politician when it came to foreign policy. Most famously, he kept an alliance with the Pharaoh Amasis II… at least until Egypt was invaded by the Achaemenid king Cambyses II in 526 BCE, at which point Polycrates looked at the situation and went "welp. Sucks to suck, Amasis". He switched sides, and even lent mercenaries to Cambyses to secure his holdings in an Egypt that was utterly decimated by the invasion. Herodotus records a slightly different story where Amasis, wary of Polycrates's success, had urged him to throw away something of immense value to basically balance his karma. Polycrates heeded the warning and chucked an extremely expensive ring into the sea. Later at dinner, they cut open a fish they caught to eat, and miraculously it was the very fish that ate the ring. Amasis called bullshit, and broke off the alliance himself, believing Polycrates was so damn lucky that when it inevitably turned, it would come crashing down. Whether or not this is a true story is anyone's guess, but either way, Polycrates's luck did eventually take a 180. In 522 BCE, around the time that Darius the Great was in the midst of usurping the throne, the Persian satrap of Sardis, Oroetus, invited Polycrates to his territory under the guise of diplomacy and security as unrest in the Empire skyrocketed. Unfortunately for Polycrates, Oroetus had a grudge against the ever elusive and overly powerful Samos, and not only did he assassinate Polycrates when the Greek tyrant arrived in Magnesia, he also had his body crucified for all to see. After Darius came to power, he punished Oroetus for acting out of line and murdering such an esteemed king, and then promptly dug Syloson out of the gutter to take Polycrates's place on the throne. Sucks to suck indeed.

Design notes, I took reference from a few 19th century depictions of Polycrates. Three of them were engravings from an 1832 book called… oh god… "Vorzeit und Gegenwart: Eine historische Lese-Gabe zur Unterhaltung und Belehrung für alle Stände", which I'm not even going to pretend to understand. Those provided the basic outlines I used for his outfit, while for the colors I referenced a 1890 illustration which sadly I couldn't trace the origins of any further than that, but it's the first picture you see on Polycrates's Wikipedia page so… there's that. Admittedly, even I think the pink looks a little dumb, but hey those dyes would've been real expensive back in the day and that's what really would've mattered to a guy like Polycrates. He appeared as one of the main villains in Chapter 2 of my D&D game set in 526 BCE. The main villain promised him riches and power beyond his wildest dreams, so he banded together with a loose coalition of warriors from across the Greek world to stop the party's advance. Each region of the map was thus blocked by a naval blockade themed around different city-states that the party had to overcome in order to progress. It was honestly quite a fun side quest for them and me as the DM. The battles really gave my party the opportunity to flex their skills against a large squadron, it could be quite a show.

Description
Polycrates was the tyrant of the island city-state of Samos during the mid to late 6th century BCE. "Tyrant" here being the ancient Greek term which was more of a neutral title than how the word is used in English today. By most accounts, the reign of Polycrates was actually an extremely prosperous time for Samos. He first came to power sometime after 540 BCE, when he and his brothers, Patagnotos and Syloson, usurped the throne from Aeaces, who was likely their father, during a festival dedicated to Hera. While initially power was split evenly between the three brothers, Polycrates gave a big middle finger to that situation. He had Patagnotos put to death, and Syloson fled, not wanting to stick his own neck out. Thus, Polycrates became the absolute ruler of the island, and he got to work turning his little corner of the Aegean into an incredibly wealthy superpower. He stocked up a fleet of triremes that gave Samos a naval dominance which would only be overshadowed by Athens later in history. This reinforced Samos's excellent position along important trade routes, thus earning them those big bucks. Hence why Samos was able to tout such famous names among their natives like Pythagoras and the Halicarnassus-born Herodotus.

Polycrates was also a shrewd politician when it came to foreign policy. Most famously, he kept an alliance with the Pharaoh Amasis II… at least until Egypt was invaded by the Achaemenid king Cambyses II in 526 BCE, at which point Polycrates looked at the situation and went "welp. Sucks to suck, Amasis". He switched sides, and even lent mercenaries to Cambyses to secure his holdings in an Egypt that was utterly decimated by the invasion. Herodotus records a slightly different story where Amasis, wary of Polycrates's success, had urged him to throw away something of immense value to basically balance his karma. Polycrates heeded the warning and chucked an extremely expensive ring into the sea. Later at dinner, they cut open a fish they caught to eat, and miraculously it was the very fish that ate the ring. Amasis called bullshit, and broke off the alliance himself, believing Polycrates was so damn lucky that when it inevitably turned, it would come crashing down. Whether or not this is a true story is anyone's guess, but either way, Polycrates's luck did eventually take a 180. In 522 BCE, around the time that Darius the Great was in the midst of usurping the throne, the Persian satrap of Sardis, Oroetus, invited Polycrates to his territory under the guise of diplomacy and security as unrest in the Empire skyrocketed. Unfortunately for Polycrates, Oroetus had a grudge against the ever elusive and overly powerful Samos, and not only did he assassinate Polycrates when the Greek tyrant arrived in Magnesia, he also had his body crucified for all to see. After Darius came to power, he punished Oroetus for acting out of line and murdering such an esteemed king, and then promptly dug Syloson out of the gutter to take Polycrates's place on the throne. Sucks to suck indeed.

Design notes, I took reference from a few 19th century depictions of Polycrates. Three of them were engravings from an 1832 book called… oh god… "Vorzeit und Gegenwart: Eine historische Lese-Gabe zur Unterhaltung und Belehrung für alle Stände", which I'm not even going to pretend to understand. Those provided the basic outlines I used for his outfit, while for the colors I referenced a 1890 illustration which sadly I couldn't trace the origins of any further than that, but it's the first picture you see on Polycrates's Wikipedia page so… there's that. Admittedly, even I think the pink looks a little dumb, but hey those dyes would've been real expensive back in the day and that's what really would've mattered to a guy like Polycrates. He appeared as one of the main villains in Chapter 2 of my D&D game set in 526 BCE. The main villain promised him riches and power beyond his wildest dreams, so he banded together with a loose coalition of warriors from across the Greek world to stop the party's advance. Each region of the map was thus blocked by a naval blockade themed around different city-states that the party had to overcome in order to progress. It was honestly quite a fun side quest for them and me as the DM. The battles really gave my party the opportunity to flex their skills against a large squadron, it could be quite a show.