Watch List notes:

Ancients
SICILY. Syracuse. Time of Dionysius I (405-367 BC). AV 100 litrae (15mm, 5.79 gm, 7h).  Struck circa 396 BC. ΣΥΡΑΚ[ΟΣΙΩΝ], head of Arethusa left in high classical style, hair pulled back into parallel waves along brow line, back held in sphendone decorated with stars, eight-pointed star behind head / Nude youthful Heracles kneeling to right, arms wrapped around neck of Nemean lion crouching left, his head pressed against the lion's back, the lion's claws pushing against his thigh and the ground. Bérend 43.8 (this coin). Spencer-Churchill 53 (this coin). SNG ANS 339 (same dies). Rizzo pl. 53, 11 (same dies). A few minor surface marks on cheek, flat spot on Heracles' leg, otherwise an exquisite and gemlike example from the very pinnacle of Sicilian numismatic artistry and possessing an impeccable pedigree to some of the greatest collections of ancient coins ever assembled. NGC MS 5/5 - 4/5, Fine Style.

From The Providence Collection. Ex DNW A11 (27 September 2011), lot 2002; Spink Gallery de Monnaise (10 October 1977), lot 110; Edward George Spencer-Churchill Collection; C.S. Bement Collection (Naville VI, 28 January 1924), lot 505; Avola/Mammanelli Hoard of 1914 (ICGH 2122).

A strong case can be made that Syracuse was the leading city in the Greek world following the defeat of Athens in the Peloponnesian War. It was by far the richest and most powerful city-state in Magna Graecia and its numismatic master engravers produced a magnificent coinage that put nearly all issues of mainland Greece to shame. The pinnacle of Syracusan power came under the reign of the "Tyrant" Dionysius I (405-367 BC). Although cruel and despotic, Dionysius was also a visionary who employed the greatest artists of his day to create what would today be called a "marketing campaign" to advance the city's image and prestige. This remarkable gold piece was likely struck circa 396 BC, after Dionysius won a great victory over Carthage at the River Anapos. The head of Arethusa, nymph of the spring of Ortygia near Syracuse, is rendered with the skill of a true master, perhaps a student of the great Euainetos whose style it closely matches. The reverse image of Heracles strangling the Nemean Lion is likewise a work of great power and pathos. The engraver has captured the moment of maximum tension, with Heracles tightening his grip around the lion's neck and mane while it claws desperately against his legs for escape. Though only a few millimeters across, the expression on Heracles' face shows both the strain of effort and a hero's determination. 

Estimate: 80000-110000 USD