1. Theagenes of Thasos
One of the towering figures of ancient sports, Theagenes was a Greek pugilist who supposedly won 1,300 bouts over the course of a 22-year career. His most significant achievements came at the Olympics in 480 and 476 B.C., when he became the first athlete to win the wreath in both boxing and pankration, an ancient form of mixed martial arts. He would win another 21 championships at the Pythian, Nemean and Isthmian games, and even won a crown as a long distance runner during a competition in the city of Argos.
Theagenes remained undefeated as a boxer for over two decades, and he continued to be a formidable presence even after his death. According to legend, when a vandal later attempted to deface a statue honoring Theagenes, the giant bronze carving fell on the man and crushed him to death.
2. Leonidas of Rhodes
Little is known about Leonidas of Rhodes, a runner who won the wreath in three categories at the 164, 160, 156 and 152 Olympic Games. Leonidas is notable not only for his long career—he won his final championships at the age of 36—but also for his versatility. He won sprint races like the stadion and diaulos, but was also victorious in the hoplitodromos, a strength-based race in which contestants ran in a helmet and armor while carrying a shield.
In total, Leonidas of Rhodes achieved a staggering 12 Olympic victories, a feat that has never been equaled in either the ancient or modern competitions. Even modern swimming star Michael Phelps has only earned 11 individual Olympic wins.
3. Gaius Appuleius Diocles
It’s easy to marvel at the astronomical salaries eared by modern athletes, but these riches are a mere pittance compared to the winnings of Gaius Appuleius Diocles, a Roman chariot racer in the second century A.D. During a 24-year career, Gaius competed in over 4,200 races, winning 1,462 and finishing second 861 times.
While there were other chariot jockeys with better records, Gaius had a knack for winning big money events, and his earnings saw him become one of the richest men in ancient Rome. According to University of Pennsylvania professor Peter Struck, Gaius Appuleius Diocles’ career winnings of 36 million Roman sesterces was enough to pay the salary of the entire Roman army for over two months—a sum that calculates to over $15 billion in modern-day cash.
4. Diagoras of Rhodes
Diagoras of Rhodes was a champion boxer and the patriarch of one of the most famous sporting families of ancient Greece. He claimed the crown at the Olympics in 464 B.C., an achievement that was later immortalized in verse by the lyric poet Pindar. He went on to win boxing titles at the Pythian games at Delphi, the Nemean games and the Isthmian games. These victories saw Diagoras become a periodonikes—an honor bestowed upon sportsmen who won at all four major festivals.
Diagoras is perhaps most famous for the achievements of his three sons, all of whom won championships in boxing or pankration. When his sons Damagetus and Acusilaus won both events at the 448 B.C. Olympics, they are said to have celebrated by carrying Diagoras through the arena on their shoulders.
5. Chionis of Sparta
A versatile track and field athlete, Chionis of Sparta swept two events during three separate Olympics in 664, 660 and 656 B.C. He specialized in the stadion and diaulos races, a pair of sprints that were among the festival’s oldest events, and his record of three consecutive victories was not replicated for nearly 200 years.
Chionis was also an accomplished jumper, and is remembered for having executed a 52-foot leap. Most historians discredit this accomplishment as an embellishment, but others have suggested that the measurement refers to the triple jump, which has its origin in the ancient Olympics. If it was indeed a triple jump, then Chionis of Sparta’s 52-foot hop was not equaled in the modern Olympics until as recently as 1936.
6. Arrichion of Phigalia
One of the ancient Olympics’ most legendary tales concerns Arrichion of Phigalia, a champion fighter whose career was tragically cut short during a title bout. According to the ancient writer Philostratus, Arrichion had claimed the wreath in pankration at the 572 and 568 B.C. Olympic games, and in 564 B.C. he reached the final for a third time in a row.
During the bout, Arrichion’s opponent placed him in a painful chokehold using his forearm. As the life was being squeezed out of him, Arrichion succeeded in dislocating his rival’s ankle—though some accounts say it was his toe—forcing the other man to tap out of the fight. While he’d won the title, it was quickly discovered that Arrichion had perished from the chokehold only moments before the fight was called. Some accounts say he died of asphyxiation, while others claim it was a broken neck or cardiac arrest. Arrichion was posthumously declared pankration champion for a third straight time, and was hailed as a hero in his hometown of Phigalia.
7. Milo of Croton
One of the true athletic superstars of antiquity, Milo of Croton was a wrestler known for his larger-than-life feats of strength and prodigious appetite. Milo won the Olympic title an astonishing six times in a row between 536 and 520 B.C., and claimed another 27 championships at the Nemean, Pythian and Isthmian games.
Milo is equally famous for his activities outside of the ring. He was a notorious glutton and reportedly could eat over 40 pounds of meat and bread and drink eight quarts of wine in one sitting He is also said to have led the Crotoniates to a military victory over the Sybarites in 510 B.C., and once saved the philosopher Pythagoras’ life by holding a collapsing roof in place until Pythagoras could escape to safety. According to legend, it was this superhuman strength that ultimately cost Milo his life. A famous tale states that as an old man he attempted to split a tree with his bare hands, but he became stuck and was eaten by wolves.