Plutarch's closing synkrisis weighs Dion of Syracuse against Brutus of Rome, judging which tyrannicide fought more nobly, more skillfully, and for purer motives.
This short comparison closes the paired Lives of Dion and Brutus, Plutarch's standard practice of following two parallel biographies (one Greek, one Roman) with a formal synkrisis that tallies their virtues and faults against one another. Dion overthrew the Sicilian tyrant Dionysius II with almost nothing behind him — no partner of Cassius's stature, no war chest built from the conflict itself — spending his own exiled wealth in advance for Syracuse's freedom. Brutus, by contrast, struck down Julius Caesar, a ruler whose power and reputation dwarfed anything Dionysius commanded, and did so while personally indebted to Caesar's clemency.
Plutarch moves category by category: who achieved more with less, who fought from necessity versus free choice, whose cause was more purely principled, and whose death was more honorably received afterward. He credits Dion with self-sufficiency and financial sacrifice, but faults him for going to war only after suffering personal injury, and for the friends who ultimately destroyed him. He credits Brutus with disinterested hatred of tyranny — he had no personal grievance against Caesar — and with the sheer daring of striking a heavily guarded, world-dominating man, but convicts him of the gravest charge of all: killing the very man who had spared his life. The essay closes with an anecdote of the later emperor Augustus (Caesar's heir) discovering a statue of Brutus in Mediolanum and, rather than destroying it, praising the Gauls for loyalty to their friend even against fortune.
Historically, this comparison matters because it shows Plutarch practicing moral history rather than mere narrative: he is not simply recording what Dion and Brutus did but building an explicit ethical ledger between a fourth-century-BCE Sicilian statesman and the assassin of Julius Caesar, using Plato's own letters as a documentary source on Dion. The passage also preserves a strikingly even-handed ancient verdict on the assassination of Caesar — written under the Caesars' own dynasty — that concedes both the nobility of Brutus's stated aim (restoring the ancestral constitution) and the ugliness of killing a benefactor, a tension that shaped how the Roman world remembered the Ides of March for centuries afterward.
“For he did not have a rival to share the credit, as Brutus had Cassius”
— Comparison Of Dion And Brutus
“Dion advanced his own wealth in support of the war beforehand, spending in advance the resources of his exile for the sake of his fellow citizens' freedom.”
— Comparison Of Dion And Brutus
“he became the very slayer of the man who saved him.”
— Comparison Of Dion And Brutus
“Dion, however, would not have gone to war had he not himself suffered ill, and this is made plain by Plato's letters”
— Comparison Of Dion And Brutus
“he called for the magistrates, declaring that he had found their city to be in breach of treaty, since it harbored an enemy of his among them.”
— Comparison Of Dion And Brutus
Plutarch does not hand down a single flat verdict; the comparison is deliberately balanced, crediting Dion with self-reliance and financial sacrifice while crediting Brutus with disinterested motive and remarkable daring. Each man's greatest praise doubles as the seed of his sharpest criticism.
Both men led armed movements to overthrow a ruler they regarded as a tyrant, Dion against Dionysius II of Syracuse and Brutus against Julius Caesar, which made them natural subjects for Plutarch's parallel-lives method of comparing a Greek and a Roman figure who faced similar moral choices.
That Brutus was saved by Caesar's clemency and even used that favor to spare fellow captives, yet still became the slayer of the man who had saved him. Plutarch says no comparable charge can be brought against Dion.
No; Plutarch argues the opposite. He notes, citing Plato's letters, that Dion took up arms only after he himself had been exiled and wronged, whereas Brutus held no personal grievance against Caesar and acted purely from hatred of tyranny.
With an anecdote about Caesar's heir finding a statue of Brutus standing in Mediolanum in Gaul; rather than destroying it, he praises the Gauls for remaining loyal to their friend even against fortune and orders the statue left in place.
Plutarch says Dion either judged badly in choosing wicked friends or, by associating with them, turned good men wicked, and adds that Plato himself rebuked Dion for the friends by whom he was ultimately destroyed.
Plutarch says yes: Dionysius was a man contemptible for spending his time in drinking, dice, and women, while Caesar's power and fortune were so formidable that even the kings of the Parthians and Indians could not sleep easy because of his name.
It is the formal synkrisis, or comparison, that Plutarch appends after the paired biographies of Dion and Brutus within his Parallel Lives, summarizing and weighing the two preceding narratives against each other.
Aemilius Paulus · Agesilaus · Agis · Alcibiades · Alexander · Antony · Aratus · Aristides · Artaxerxes · Caesar · Caius Gracchus · Caius Marius