Obv: Head of Heiron I facing left. Rev: Horseman Prancing right holding spear beneath in ex. ieprosnoz (in Greek). Metal: Bronze 20.9 grams, 27 mm diameter. Condition: VF/F.

In 416 BC, the Sicilian city of Segesta requested Athens to aid them against Selinus (a city backed by Syracuse). Athens decided to take this opportunity to conquer Sicily as a spring board against Carthage. In 414 BC, the Athenian fleet under the Athenian general Nicias attacked Syracuse. After initial victories outside the city walls, Nicias decided to withdrawal to Katane for the winter. In the meantime, Syracuse strengthen its walls and got assistance from Sparta and Corinth. In the spring of 414 BC, the Spartan general Gylippus attacked and defeated the Athenians. Nicias requested that the war be called off, but instead Athens sent additional ships. However on 20 September 413 BC, Gylippus defeated the Athenians at sea. This was Athens first major naval defeat and the start of the end for Athens.

In the 3rd century BC, Heiron II was king of Syracuse and made an alliance with Rome against the Carthaginians during the First Punic War (264 - 241 BC) giving the Romans a valuable base for military operations. After the war, Sicily was conceded to the Romans and became the first Roman province. Herion II was permitted to continue his rule for the rest of his life, but in 212 BC Rome sacked Syracuse and put all of Sicily under their rule.