[1] He was admitted by the Alexandrian critics into the canon of historiographers, and his work was highly valued by Alexander the Great.

Before his rise to power, Dionysius criticized the generals of Syracuse on their poor performance against the Carthaginians, and was fined by the assembly for his seditious language.

[citation needed] In 386 BC, without consulting the tyrant, Philistus married the daughter of Dionysius' brother Leptines.

Dionysius feared that Leptines and Philistus would use the marriage as the basis of an alliance against him, and exiled both men from Syracuse.

[2][clarification needed] When Dion set sail from Zacynthus with the object of liberating Syracuse in 356 BC, Philistus was entrusted by Dionysius II with the command of the fleet.