Diogenes Laertius Life of Timon in Bk IX....and whenever he was disturbed by his maid-servants or by the dogs, he paid no attention to them, studying above all things to live in tranquillity.
However, things are not so dark concerning Stilpo's dates. In his Life Diogenes states that Stilpo was himself the pupil of either Euklides of Megara, or Thrasymachos of Korinth (an error for Chalcedon).Euklides dies c.380 which would make Stilpo born c400 which is far too early. Thrasymachos was a pupil of Euclides and it is probable that those stating Stipo studied under Euklides were decieved by a notice that he studied at the school of Euklides. Thrasymachos has been assigned to c430 on the basis of a fragment of Aristophanes dated to 427, however he is linked there with Alkibiades
and this Thrasymachos is linked to the 'law-men'; I doubt this is the same man.Father: Well, you'll get your come-uppance in time, my lad! Son: Ha! That 'get your come-uppance' is from the rhetoricians. Father: Where will all these fine phrases of yours land you in the end? Son: 'Land you in the end' - you got that from Alcibiades! Father: Why do you keep making insinuations (hypotekmairei) and slandering people who are just trying to practise decency? Son: Oho, ho! O Thrasymachus! Which of the law-men came up with that piece of Jargon?' Dillon, John; Gergel, Tania (2003). The Greek Sophists. Great Britain: Penguin Group. p. 205. ISBN 0-14-043689-8. Hypotekmairei is a hapax legomenon, and occurs nowhere else in surviving literature. Dillon and Gergel assume that the word had some technical definition, possibly given to it by Thrasymachus.
Clement of Alexandria, Stromateis VI 1 records that he was commissioned to write a speech for the Larissans against the territorial ambitions of Kind Archesilaos, who died in 399. Aristotle mentions him in the context of rhetorical development as coming after Teisias (On Sophistical Refutations 183b22-34); Teisias was famously the pupil of Korax himself involved in property disputes occaisioned by the seizure of power at Syracuse of Thrasyboulos which occured in 466, this seems to have been the beginning of his career,say at 25 taking a pupil at 40 would make Teisias c451 a thirty year career would bring the terminus post quem to 421, which we might consider the latest possibility for Thrasymachos' birth (having 'For Larissa' commisioned when 21. His career, then could reasonably extend to 360ish which would make Stilpo born c375 at the latest and thus c 68 in 307 when he encountered Demetrios.
We can further investigate this hypothesis by considering the named pupils of Stilpo.
Menedemos is an interesting case as he gets a life of his own. The most important remark comes at the end thereof, Herakleides says he lived to 74 and Diogenes quotes from a vote of thanks for Gonatas’ victory over the Gauls at Lysimacheia in 277. He cannot, therefore have been born before 351; this in turn means that the earlier statement, that he studied at the Academy under Plato, must be in error since Plato died in 347 and did not admit four year olds! He was also meant to be deserting from a body of Eretrian soldiers being sent to garrison Megara. Any context before 338 would make these Athenian allies and so deserting to Athens would be a nonsense.
After the Lamian War Antipater established garrisons in several Greek cities, it is not stated but Megara’s strategic importance must make it a good candidate for being garrisoned (and it is implied by Diodoros XVIII 46) and 320 would make Menedemos 21 a much more appropriate age for military service and where better to abscond, than the Strategos’ late enemy?
Later he moved next to Stilpon in Megara with Asclepiades of Phlius and they both became his disciples for an unspecified length of time before becoming a follower of Phaedo and proceeding to the Court of Nicocreon in Cyprus, a monarch not mentioned during the Salamis campaign and presumed to have died before 306.
Menedemos went on to found the ‘Eretrian School’ upon which Phaeros wrote under Philopatros.
Timon is another case; he was studying dance but abandoned his studies to study under Stilpon. He then returned to Phlius, married and moved to Elis to see Pyrrhon, who studied under Bryson the successor to Stilpon before leaving with Anaxarchos on Alexander’s Expedition. Timon raised a family and then went to Chalcedon to make his fortune as a Sophist and then moved to Athens where he stayed but for a short sojourn in Thebes (thus after 316 when Kassander rebuilt it). It is only a guess but Demetrios Phalerios went to Thebes after his ejection from Athens in 307 perhaps his fellow sophist went with him returning when Demetrios’ regime proved to be more beneficent than expected.
Timon lived to be ‘nearly ninety’ and had the acquaintance of Antigonos Gonatos and Ptolemy Philadelphos, given his Athenian residence a context around the Cremonidean War would seem right so if he died 260 he would have been born c 350.
So on this evidence it would seem that Stilpon flourished in the mid to late fourth century and that he would barely have made it into the third, meaning that if Kleitarchos did not join his School in 309 it was most likely earlier rather than later.
Hereendeth part one.