In the 20 years since his suppression of the Catilinarian Conspiracy as consul in 63 BCE, Cicero had a checkered political career: exile at the hands of Clodius for his execution without trial of the citizen-conspirators, an uneasy accommodation with Caesar and Pompey after his recall, a lukewarm involvement in the civil war, and years in solitude composing philosophical tracts. As if throwing off 20 years of malaise, Cicero propelled himself into events following the assassination of Caesar. Cicero was not a party to the assassination, but he wasted no time in praising the tyrannicides and the newly asserted liberty. He was now the elder statesmen for a new generation of political leaders; most of his contemporaries had died either from age or from the violence of the civil wars.

Cicero publicly aligned himself with Brutus and Cassius and sought to take under his wing Octavian, Caesar's grandnephew and adopted son, a political neophyte, though wise and ruthless beyond his years. In late 44 and early 43 BCE, the senate, led by Cicero, attempted to turn Octavian to their side and against Mark Antony. For a brief time, this strategy was successful, but Cicero would soon learn what many others have, that a “fateful alliance,” rather than caution or outright opposition, with an ambitious, yet inexperienced, political outsider can fail tragically. Cicero viciously tore into Antony in his famous Philippics, 14 speeches named after the orations against King Philip II of Macedonia by the Athenian orator Demosthenes. The speeches (some were published without being delivered) called Antony every name in the book—a drunkard, a gambler, and a whore-monger. Whether one agreed with Cicero or not, such language was in 43 BCE standard fare for how Romans frequently spoke and wrote about rival politicians. Simply put, Rome enjoyed free speech, lots of it. When Cicero composed his speeches and philosophical tracts, some of the most influential writings in Latin and European literature, no doubt he thought a great deal about what people would think of them—would his words be persuasive, would they stand up to his reputation, would they have their intended effect upon his audience? We can never be certain if Cicero ever thought about whether his words would get him imprisoned, exiled, or killed; given the ferocity with which Cicero attacked his political enemies, it seems that this was not foremost in his mind.