The all-time greats
of the Ancient
Olympic Games

A magical collection of characters light up the accounts of almost 12 centuries of action at the Ancient Games. Huge, heroic men caught the attention with the stars of the combat sports particularly adored. Their physique, love of a challenge and extraordinary appetites chimed with a public brought up on the immortal heroes of Greek mythology. Here, we pick out the best of the best.



Theagenes of Thasos

At Olympia: One of the most adulated athletes in antiquity, Theagenes won the pankration at the 76th Olympiad in 476BC, having won the boxing title at the previous Games.

Back story: Born on the island of Thasos to a priest of the temple of Herakles, the locals came to believe Theagenes was in fact the progeny of the God himself.

Favourite fact: This giant of a man spent his life touring the Mediterranean, competing in ancient Games at which he was reported to have won more than 1,400 victory wreaths.

Magical myth: The people of Thasos erected a statue in honour of their great hero but one of his biggest rivals was unimpressed. Having been beaten continuously into second place by Theagenes, the man came to the statue each day and whipped it vigorously until one day it inexplicably fell off its base and killed the vengeful man. Even in death, Theagenes could not help but win.

And a special mention goes to… Arrichion of Phigaleia who, with his final breath, forced his opponent to concede defeat. He was posthumously awarded an Olympic wreath.



Milon of Croton

At Olympia: Six-time Olympic champion.

Historian’s view: “Almost everyone’s favourite is Milon of Croton. He was famously huge, this enormous guy. As part of the big sacrifice (to Zeus held during each Games) he carried a cow into the sanctuary on his back, killed it and then ate the whole cow himself in a single day. He is a huge, gluttonous figure,” said Paul Christesen, Professor of Ancient Greek History at Dartmouth College, USA.

Favourite facts: Reported to have once downed nine litres of red wine in one go, Milon led Croton into battle wearing a lion skin on his back, a crown on his head and carrying a club.

Final Games: Estimated to have been 38-40 years old, Milon reached the final in his seventh Olympic Games. After a long, drawn out battle he surrendered wearily to 28-year-old Timasitheos. At this point the crowd swarmed forward and hoisted Milon on to their shoulders, with Timasitheos leading the cheering.

Fitting end: Tangled in a tree in the wild, having tried to split open its withered stump with his bare hands, Milon was eaten by wolves.


And a special mention goes to… Hipposthenes of Sparta and his son Etoimokles. Between them the pair won 11 Olympic wreaths, yet they struggle for recognition due to the all-consuming figure of Milon.




Diagoras of Rhodes

At Olympia: Victor in the 79th Olympiad in 464BC.

Back story: Recorded by Grecian scholar Pindar to be 2.20m tall, stories spread alleging that his mother had lain with a god.

Favourite fact: Nick-named euthymaches, meaning ‘fair fighter’, Diagoras would stand face-on to his opponent, never ducking, weaving or swaying out of the way of any punches.

Olympic dynasty: His three sons won five Olympic titles between them.

Fitting end: Diagoras watched one son win the boxing and then another claim the pankration crown soon after. Both gave their wreaths to their father and the delighted crowd lifted the old champion on to their shoulders. At this point one of the crowd is said to have shouted out something along the lines of, “surely it doesn’t get better than this? You may as well die now”. At which point Diagoras did exactly that.

And a special mention goes to… the long-haired Pythagoras of Samos who turned up to compete in the boy’s section in 588BC but was barred due to his effeminate appearance. He took part in the men’s competition instead and won.




Leonidas of Rhodes

At Olympia: One of the greatest Olympians of all-time, ancient or modern, Leonidas won both prestigious sprints, the stadion and the diaulos, and the race in armour at four successive Games, 164BC-152BC.

Favourite fact: Leonidas was 36 years old by the time he won his 12th Olympic wreath.

Reaction in Rhodes: Said by his countrymen to “have the speed of a God”, he was deified in his own lifetime.

Incomparable: While plenty of runners came close, no one ever matched his achievements.

And a special mention goes to… Astylos of Croton who, after winning the stadion and diaulos in 488BC, changed his allegiance and ran for Syracuse in the following two Olympic Games, at which he won both races again. The people of Croton did not take kindly to this switch and turned his family house into a prison. 




Phayllos of Croton

At Olympia: Very little is known about individual stars of the pentathlon or about those events within it which were not contested separately; the long jump, discus and javelin. Phayllos is a rare exception to this rule. But while he is known to have won three victories at the Pythian Games, it is not clear what he won at Olympia.

Back story: He competed in the late sixth and early fifth century BC and became a firm favourite of the Greeks, principally thanks to his heroism in battle.

Favourite fact: Phayllos is reported to have soared over the entire 15.2m-sandpit at one long jump competition, registering an incredible 16.3m. It is one of the very few times an exact distance has been recorded in Antiquity. Given that it is physically impossible to jump that far (the current men’s long jump world record stands at 8.95m, held by Mike Powell, USA), this distance prompted a discussion that perhaps ancient athletes competed in what we refer to as the triple jump. However, most scholars have now discarded that theory, putting the impossible distance down to embellishment.

Military hero: The man from Croton was hailed by all Greece after the victorious naval battle of Salamis in 480BC. The only Greek from southern Italy to take part, Phayllos commanded his own ship, paid for out of his own pocket. In return a statue of the man was erected on the Acropolis of Athens, the inscription of which survives today. 150 years after the battle, Alexander the Great also sent part of the treasure he seized in Persia to Croton in recognition of Phayllos’ dedication.




Kyniska of Sparta

At Olympia: Won the four-horse chariot race in 396BC and 392BC.

Back story: Daughter of the King of Sparta, Kyniska had her sights set on Olympic glory from an early age. Permitted by custom to win an Olympic wreath as the owner of a chariot, she evaded the rules banning women from competing.

Trend setter: Kyniska’s victories set the way for female owners, with a total of 12 claiming victory by the end of the Games.

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