During the decades leading up to Julius Caesar's dictatorship, Roman coinage took on an increasingly personal character, displaying designs with a clear propagandistic message promoting the family or the political favorites of the moneyer who struck the coins for that year. Types commemorated victories, beneficent legislation, famous ancestors, and the like. The trend reached an extreme in early 44 BC when Caesar, stockpiling money to pay for his imminent Parthian campaign, had coins struck with his own portrait, a first for the official coinage of Rome (the images of living Romans had appeared on coins at the periphery of the empire as early as ca. 196 BC, but never on Rome's official state issues). This move was counted as one among many which showed Caesar's tendency towards monarchical behavior and which resulted in his assassination.Far from removing this problem of self-aggrandizement on coinage, however, Caesar's death left the field open for a wide array of would-be rulers who copied the trend to promote themselves, first among the soldiers who supported their causes (for pay and rewards of booty), secondly among the rest of the populace. Thus, we have today a most interesting numismatic documentation of portraits and propagandistic messages of the men who struggled for power in the political vacuum left by Caesar's sudden departure; more to the point, we also can trace the rise to power of Octavian, who ultimately became Rome's first Emperor, known otherwise as Augustus. These are presented below.