This expression alludes to the fable of the Tortoise and the Hare which is one of more than 700 "Aesop fables." According to Greek historian Herodotus, Aesop was a slave in Greece who lived from about 620 to 560 B.C.E. and won his freedom through telling moral stories.
However, Herodotus was not born until about 80 years after the time period when Aesop is said to have lived and so many scholars question whether Aesop actually existed or whether a certain type of moral fable in the oral tradition simply got attributed to him.
At this far remove, whether Aesop is an historical figure or not is unlikely to ever be proved one way or another, but what is clear is that only some of the tales attributed to him can be traced back to the 5th century B.C.E., with a good number having their roots in more modern times.
It is likely that the stories were part of the oral tradition for hundreds of years before they were first written down in Greek; and later translated into Latin. The first English edition of Aesop's Fables dates to 1494 but did not include the story of the Tortoise and the Hare, because European editions of that time were translations of a Latin collection that did not include the story, even though it was in an earlier Greek collection. The first known inclusion of the story of the Tortoise and the Hare in a European collection was in French in 1547; its first inclusion in English was in 1667.
Where the story gets intriguing is that way back in 490 B.C.E., Greek philosopher Zeno created the Achilles and the Tortoise paradox in which he argues that, if a tortoise and the legendary warrior Achilles were to race each other with the tortoise being given a head start, mathematically speaking, Achilles would never catch up if the tortoise keeps moving. The logic of this is beyond our ability to understand, let alone explain, but Wikipedia has an expansive article on the topic if you wish to know more. But it does make us wonder whether the fable we know today of the Tortoise and the Hare perhaps has its roots in Zeno's paradox?
As to whether a tortoise could win a race against a hare, this was put to the test a few years ago with a rabbit substituting for the hare -- and the tortoise won!
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