In the late 5th century BC, Syracuse emerged as a hub of innovation in Greek numismatics, driven by its need to finance mercenaries and expand its hegemony. This period saw the creation of high-denomination silver coins that served as canvases for some of antiquity's most brilliant engravers, including Euthydamos and Eumenes. Their tetradrachms, struck during the Second Democracy (466–405 BC), introduced groundbreaking artistic elements. On the obverse, a winged male figure, possibly Eros, drives a chariot while Nike crowns him, with the dynamic horses depicted mid-motion.

Beneath the scene lies the mythological Skylla, a blend of human and sea serpent forms, unprecedented in Syracusan coinage. The reverse features a finely detailed head adorned with plaited hair and barley, often interpreted as Persephone, signaling a departure from the earlier depictions of Arethusa.

This era marked a shift in Syracusan coinage, characterized by artistic dynamism and the increasing prominence of engraver signatures. Earlier static horse depictions were replaced by action-packed scenes, reflecting the city’s cultural and military vibrancy during its conflict with Athens (415–413 BC). The chariot designs incorporated foreshortening and intricate details, such as the contours of the horses and the charioteer. The obverse, with its winged figure and maritime motif of Skylla, possibly alludes to Syracuse's naval victories, particularly against Athens. Such innovations inspired engravers across Sicily, including those at Selinus, whose coins share stylistic similarities with Syracuse’s dynamic designs, suggesting possible collaboration or influence.

Syracuse’s position as the dominant Greek city of Sicily underpinned its artistic achievements. Founded around 733/2 BC by Corinthian settlers, it flourished into a major power, ruling extensive territories in Sicily and southern Italy. Despite political instability and frequent conflicts, the city maintained its cultural prominence. The tetradrachm in question likely dates to the early reign of Dionysios I (405–367 BC), though it may have been struck during the final years of the democracy. Its obverse imagery of Skylla, tied to maritime symbolism, and the reverse depiction of Demeter or Kore underscore the coin’s role not only as currency but as a celebration of Syracusan identity and triumphs.

SICILY, Syracuse. Second Democracy. 466-405 BC. AR Tetradrachm (28mm, 16.96 g, 1h). Dies signed by Euth- and Eumenes. Struck circa 415-405 BC. Nike as charioteer, holding reins in both hands, driving fast quadriga right; above, Nike flying left, crowning charioteer with wreath; in exergue, Skylla, holding trident, swimming right; behind her, dolphin swimming right; EVΘ before / Head of Arethusa left, wearing wreath of grain ears, and necklace with lion head ornament; EVM below neck; four dolphins and [ΣV]PAKO-ΣIΩИ around. Tudeer 46 (V15/R28); SNG ANS 273; BMC 153; Rizzo pl. XLIII, 11; Basel 460; Gulbenkian 279; Jameson 796; McClean 2714; Hunterian 45 (all from the same dies).

Ex Numismatica Ars Classica 52 (7 October 2009), lot 76; Numismatica Ars Classica 29 (11 May 2005), lot 118; Numismatica Ars Classica 8 (3 April 1995), lot 162.