He is also mentioned in passing by Plutarch[1] and Synesius;[2] a pupil of Socrates, Phaedo of Elis, is known to have written a dialogue called Simon.
[5] Indeed, Simon’s excellence in the art of shoemaking would have been a form of expertise that Socrates, of Plato's Apology,[6] held up as the only example of genuine knowledge.
I admit that I am a shoemaker and that I do work of that nature, and in like manner I would, if it were necessary, cut straps once more for the purpose of admonishing foolish men who think that they are living in great luxury.
[11] Stobaeus preserves one:[12] Zeno said that Crates was sitting in a shoemaker’s shop and reading aloud Aristotle’s Protrepticus, which he had written for Themison, the Cyprian king.
[10] Archaeological investigations have revealed the remains of a shop near the Tholos in the southwest corner of the Agora of Athens which has yielded quantities of hobnails and a pot base with the word "Simon's" (Greek: ΣΙΜΟΝΟΣ) inscribed on it.
[10] In the recording of Simon's dialogues, Diogenes Laërtius' lack of order and the repetition of some titles point against the works being fabrication.
[7] R. F. Hock concludes that the lack of information and interest on Simon the Shoemaker is testified by the fact that he "came to function in a very specific context" and he "was admired really only by strict Cynics.
[7] As with Simon himself, the reality of these lost works has also been doubted, but the lack of any order in Diogenes’ list and the repetition of some titles point against its being a fabrication.
The titles of his works are as follows:[17] However, in recent times it has been argued that what Diogenes Laërtius meant was, rather, that Simon had been the first with whom Socrates entertained philosophical conversations.