Milo kept on competing, even well after what would have been considered a normal Olympic athlete's prime; by the 67th Olympiad, he would have been over 40 years of age.
Diodorus Siculus wrote in his history that Milo was a follower of Pythagoras and also that he commanded the Crotonian army which defeated the Sybarites in 511 BC, while wearing his Olympic wreaths and dressed like Heracles in a lion's skin and carrying a club.
The Crotonians had but an hundred thousand, which were commanded by Milo the wrestler, who at the first onset put to flight that wing of the army which was opposite to him: for he was of invincible strength, and had courage answerable to his strength, and had been six times victor at the olympic games; when he began his fight, he was crowned with olympic wreaths, wearing (like Hercules) a lion's skin and a club; at last he gained an absolute victory, and thereupon was much admired by his countrymen.Milo's death became a popular subject in art in late Italian Renaissance sculpture, continuing to around 1900, allowing the sculptor to show his skill in a dramatic anatomical pose.
His final test of strength came when he was traveling the countryside and met a villager trying to split a stump with hammer and wedges.
Milo immediately tried to pull the stump apart by inserting his fingers in the crack where the villager had driven the wedges.
Legend then says that Milo met his end when wolves, or a lion, took advantage of his predicament and descended upon him.
He came to Olympia to wrestle for the seventh time, but did not succeed in mastering Timasitheus, a fellow-citizen who was also a young man, and who refused, moreover, to come to close quarters with him.