Julius Caesar was the first living person whose portrait appeared on a coin struck at Rome. Portraiture on coinage was considered a mark of kingship, a form of government at odds with Roman Republican values. While Caesar never allowed himself to be formally recognized as king, extraordinary honors and privileges had effectively made him the sole ruler of Rome by the mid-40s B.C. To those already concerned about Caesar's growing power, coins issued in early 44 B.C. featuring his portrait would have provided tangible proof of his royal aspirations.

These initial coin portraits of Caesar, showing him with wrinkled neck and sunken cheeks, conform to the stylistic norms of Roman Republican portraiture, which tended to accentuate signs of advanced age. However, certain aspects of Caesar's appearance allude to his exceptional status; for example, he wears a laurel wreath, ordinarily reserved for generals celebrating triumphs but worn by Caesar on all public occasions. The legend "CAESAR DICT QVART" accompanying the portrait head pictured here commemorates Caesar's designation as dictator for the fourth time, an unprecedented extension of authority normally granted for short-term emergencies.

On March 15, 44 B.C., a group of senators, convinced that Caesar intended to dismantle the Roman Republic, stabbed him to death. Brutus, the leader of the conspiracy, soon left Rome to prepare for war with Caesar's supporters. To pay his troops, Brutus issued coins. One of these, a rare denarius whose reverse is shown, presents Brutus's role in the assassination as a strike in defense of freedom from tyranny. A pair of daggers flanks a pileus, a felt cap symbolizing liberty, above the legend "EID MAR," referring to the date of Caesar's death according to the Roman calendar.

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