In the four Olympics in which he represented his city he went undefeated in the sport of wrestling. He proudly displayed his four wreaths as he walked the streets. His fellow town people must have thrown confetti at him since he was their hero. (They did not use medals then, just thorny olive branches. They also participated in all sports in the buff. Well not really, they soaked their bodies in olive oil to make their muscles shine in the sunlight.)
There is no grounds for questioning that he was a historical person. He is mentioned by many classical authors, among them Cicero and Suidas. It is not surprising that a number of legendary stories developed around his name.
Legend has it that he would train in the off years by finding a newborn calf and he would walk around with it on his back every day until the Olympics took place. So by the time the events were to take place, he was carrying a four year old cow on his back to the games, naked. That must have been a sight.
The interesting thing about Milon is that he thought he was Heracles. So one day when he approached a woodsman unable to finish his daily work of cutting down a huge tree, Milon offered to finish it for him. The woodsman said thank you and went off to take care of some other chores and said he would be back later in the evening with some food for his help. Unfortunately he did not keep his word. He was undoubtedly grateful, but probably was scared at the sight of a 300 pound muscular naked man cutting down a tree with a cow on his back
So Milon sized up his task made a fist and started to hammer the wedges in the base of the tree with his fist. The tree collapsed on his hand and he was unable to get it out. When the woodsman came back the next day he saw Milon half eaten by wolves and his hand stuck in the tree.
A sculpture by the French artist Pierre Puget (1620-1694) can be seen here: http://www.tigtail.org/TVM/X1/f.Baroque/c.french/puget/puget
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