The Best Troll Rome Ever Knew

Edward Watts reviews Josiah Osgood’s “Lawless Republic: The Rise of Cicero and the Decline of Rome.”

By Edward WattsAugust 19, 2025

• History

• Law

IT HAS BEEN nearly 30 years since Bill Clinton stood on the White House lawn following the House impeachment vote and implored Americans to “stop the politics of personal destruction” and “get rid of the poisonous venom of excessive partisanship, obsessive animosity, and uncontrolled anger.” We have, of course, not done this. Americans have instead become addicted to the intoxicating rage that venom produces before it kills. As we have made nearly everything in life political, the impulse for inflicting personal destruction has followed. Battles once fought over the reputations of the most powerful people in the nation have spread into confrontations at school board meetings, arguments between PTA members, and random attacks by social media mobs that leave ordinary people bewildered, traumatized, and, most of all, so uncontrollably angry that they lash out at others.

The cycle of conflict, bewilderment, and anger that has consumed the United States over the past three decades reflects something deeper and much more dangerous than a general inability to handle the communication technologies of the internet age. Unsettled political systems destroy their citizens’ sense of appropriate behavior toward one another. At one moment, someone might revel in the destruction of an adversary’s reputation through a quip applauded by a semi-anonymous gallery of observers. The next moment might bring terror that their own reputation is about to be destroyed if their target responds with a devastating reply. And beneath it all is the “obsessive animosity” and “uncontrolled anger” that Clinton spoke about. This is our country in 2025. As Josiah Osgood’s new book Lawless Republic: The Rise of Cicero and the Decline of Rome shows, it was also Rome in 55 BCE. And we know the catastrophe that Roman representative democracy suffered because citizens continued to empower ancient edgelords and the militias that followed them.

Lawless Republic profiles Cicero, perhaps the best troll the Roman world ever knew. Relying on a series of speeches Cicero made in criminal cases and Senate meetings between 80 and the mid-40s BCE to reconstruct his life and career, Osgood transports the reader into the Roman Forum at regular intervals during these four decades, showing how the trauma and corruption injected into Roman life by the dictator Sulla in the 80s steadily corroded trust in representative democracy and coarsened Cicero’s rhetoric.

Although Cicero was never kind to the people sitting across the tribunal from him, his attacks grew increasingly vicious as the years progressed. And the reactions of his opponents did too. Remarks that might have elicited gasps and headshakes in 80 BCE incited threats of physical violence from angry mobs in the 50s. These changes stand out so starkly to readers of Lawless Republic because, as each chapter jumps a few years into the future, one is immediately struck by how much Rome changed in the intervening time.

This chronological structure works well because Osgood carefully layers contextual descriptions, historical exposition, and dramatic storytelling across each chapter. After introducing Roman criminal procedures and the physical space in the Forum where trials were held, Osgood begins with Cicero’s defense of the accused parricide Sextus Roscius Jr. in 80 BCE. This criminal case arose in the chaotic aftermath of Sulla’s dictatorship and involved an associate of Sulla colluding with Roscius’s relatives to kill his father, take the family’s estates, and frame the son for the murder. Cicero uncovered the plot, presented its outlines to the jury, and secured Roscius’s acquittal by focusing on the motives of those prosecuting him. Even Cicero’s attacks on the luxurious lifestyle of Lucius Cornelius Chrysogonus, the freed slave and Sullan ally who appears to have masterminded the scheme, were relatively mild compared to what we would later see.

Cicero won the Roscius case, but his performance also highlighted the young, skinny orator’s physical and rhetorical deficiencies. Cicero packed his speeches with ponderous subordinate clauses that invited listeners’ minds to wander as they waited for the verb that, almost invariably, concludes each Ciceronian thought. In some cases, the verb would remain concealed for a minute or more as Cicero droned on in sentences that fill nearly half a page in modern texts. Cicero himself was too physically weak to project his voice across the Forum as these sentences meandered to their conclusion. Such limitations would simply not work for the ambitious young man, so, Osgood explains, Cicero went to Greece and embarked on a training program that combined exercises in gymnasiums with intensive rhetorical and philosophical training.

Cicero returned to Rome a much more formidable speaker who could better deploy his stylistic creativity and lacerating wit. In 70 BCE, he argued the case that would mark him as Rome’s foremost courtroom advocate. Cicero faced off against Hortensius, Rome’s reigning king of judicial advocacy, and successfully prosecuted Gaius Verres, a dishonest governor of Sicily whose extrajudicial execution of a Roman citizen, as well as his large collection of artistic masterpieces extorted from their Sicilian owners, demonstrated his obvious guilt. And yet many Romans doubted that Verres would ever pay for his crimes because of the deep corruption of the Roman courts. Osgood explains how Cicero overcame procedural delays, crooked jurors, and witness tampering by expanding his prosecution of Verres to include attacks on Hortensius for bribing jurors and for his complicity in Verres’s Sicilian plundering. When Verres fled to Massilia (today’s Marseille, France) before the verdict, Cicero’s victory offered fuel for his rapidly accelerating political career. In a little over six years, he won elections to serve as aedile, praetor, and finally consul, Rome’s highest office. Personal attacks worked.

Osgood also reveals how the public insults and blatant corruption of the 70s metamorphosed into acts of physical violence and murder in the 60s. Osgood focuses on two moments that transformed Cicero’s public and personal life. The first occurred when Cicero served as consul and directed the Senate’s response to Lucius Sergius Catiline’s attempt to overthrow the republic in 63 BCE. Although the orations Cicero delivered during this crisis were (and still are) rhetorical masterpieces, his decision to condemn without trial a group of Roman citizens accused of conspiring with Catiline tainted his legacy. Their executions not only broke Roman law but also echoed the most damning charge that Cicero had leveled against Verres a few years earlier. Public opinion quickly turned against Cicero.

The second moment occurred less than two years later when Cicero testified in the trial of Publius Clodius Pulcher, a charismatic young politician who was discovered sneaking into a religious ceremony where only women were allowed. Clodius led a gang of devoted, sometimes violent followers and realized that he could arouse wider public support for himself by mobilizing people against Cicero. Cicero fought back with devastating put-downs and allusions to Clodius’s rumored incestuous liaisons, but Clodius ended up buying the votes of enough jurors to secure his acquittal.

Osgood traces how the conflict between a vindictive Clodius and an eristic Cicero upended the orator’s life for much of the next decade. Cicero continued to pound away at Clodius’s reputation, but Clodius did far more damage to Cicero. He passed a law sending Cicero into exile, had his supporters destroy Cicero’s house, and then tried to block any reconstruction by erecting a shrine to the goddess Liberty on the site. For Clodius, the politics of personal destruction had ceased to be metaphorical. And Cicero, Osgood argues, lost many of the material things that were most important to him and suffered damage to his marriage and other personal relationships that he could never repair.

Cicero returned to Rome in 57 BCE after a 17-month exile, but he could not escape the threat of Clodius and his gang until Titus Annius Milo, another Roman politician whose activities blended traditional campaigns and street fighting, killed Clodius in a roadside brawl. Milo was tried for murder, with Cicero serving as one of his defenders, but on the day of the trial, Cicero could only give a short speech before he was intimidated into silence by crowds who had once supported Clodius. Osgood explains that Cicero responded by revising his original oration, which presented Milo’s killing of Clodius as an act of self-defense, into a longer published speech that instead endorsed the vigilante murder of people who posed a threat to civil order. Cicero knew firsthand how destructive political violence could be, but he had stopped caring.

Lawless Republic culminates with a concise, powerful description of how Cicero’s pugnacity, gift for crafting biting insults, and political tone-deafness led to his death in 43 BCE. Osgood describes Cicero’s flailing attempts to find his political footing after Julius Caesar’s crossing of the Rubicon revealed the hollowness of the Roman republican system. Stripped of the political protections that had enabled him to speak so forcefully in the past, Cicero fled Caesar and joined Pompey’s resistance army. But he could not keep his mouth shut. “Even in war,” Osgood writes, “Cicero couldn’t refrain from wisecracking” as he mocked Pompey’s tactics. This contributed to the senatorial backbiting that forced Pompey to launch a disastrous (and strategically unnecessary) attack on Caesar’s besieged forces at Pharsalus in 48 BCE. After Caesar prevailed and Pompey was killed in Egypt, Cicero crept back to Italy to beg for Caesar’s forgiveness.

Caesar pardoned Cicero, who retreated into a sort of political retirement. He reemerged briefly following Caesar’s murder to try to convince the assassins to target Mark Antony, the deceased dictator’s most capable ally. When that failed, he knew his best choice was to leave Italy and sit out the civil war he knew would come. Cicero could not, however, resist one final public attack on Antony in the Senate house. The speech he gave was relatively mild, but Antony responded by criticizing Cicero’s conduct during his consulship. Cicero then did as he had learned to do over the past 40 years. As Osgood explains, “he subjected Antony’s own life and career to an excoriating review,” detailing his drunkenness, forgeries, debauchery, and friendships with pimps and prostitutes. Cicero ultimately composed 14 speeches assailing Antony that got more aggressive and vicious as the series progressed. It was, Osgood writes, “thrilling for Cicero […] to play a leading part in public affairs again.”

But Cicero misread the situation in Rome. He had made an alliance with Octavian—the 19-year-old who would eventually become Emperor Augustus—that Cicero believed freed him to attack Antony with the cutting language he had deployed in the 50s. When Cicero tried to dispose of Octavian in 43 BCE, however, Octavian quickly turned on the orator, made an agreement with Antony, and stood aside as Antony added Cicero’s name to the list of people he wished to condemn to death. Cicero was decapitated and his head and hands nailed to the Rostra in the Forum to show all Romans how rhetorical assaults would now be handled.

The increasingly brutal verbal battles in Roman courtrooms developed into “tests of power between groups” who believed that judicial corruption gave wrongdoers “a decent chance of winning in court” and who did not hesitate to take up arms if a trial did not go their way. This is how someone like Cicero, who knew that political violence destroys free societies and who once prosecuted a man for killing a Roman citizen without a trial, “came to embrace violence over the course of his political career,” Osgood concludes. It seemed necessary in the moment. It was catastrophic in the long term. Osgood quotes the Roman historian Livy, who wrote that Cicero “suffered nothing crueler from his victorious opponent than what he would have done, if he had enjoyed the same success.”

This, unfortunately, is where our own politics of personal destruction may lead as we push each other toward greater viciousness and violence. Lawless Republic shows how the small, daily steps we take toward casual cruelty desensitize each of us until, ultimately, we become willing to overlook the humanity and basic rights of our fellow citizens. The abyss then awaits unless, unlike Cicero, we realize that the barbs we direct at others also harm us by eating away at our own empathy and humanity. The best way to avoid Cicero’s end is to turn back from the path of obsessive animosity and uncontrolled anger now, while we still can.