The Top Benevolent and Malevolent Dictators From History
The Top Benevolent and Malevolent Dictators From History

The Top Benevolent and Malevolent Dictators From History

Khalid Elhassan - November 30, 2020

“Dictator” and “tyrant” are dirty words today, and rightly so. Millennia ago, however, tyrants were wildly popular in Ancient Greece, and a dictator was a highly respected position in the Roman Republic. Good tyrants or benevolent dictators were not just propagandistic descriptions, but actually existed. As was inevitable, however, bad tyrants and not-so-benevolent dictators eventually emerged, to demonstrate the downside of one-man rule and give those words the bad odor they carry today. Following are thirty-five things about some of ancient history’s good and bad tyrants, and benevolent and non-benevolent dictators.

The Top Benevolent and Malevolent Dictators From History
Sacha Baron Cohen’s ‘Dictator’ reflects the modern distaste for dictatorship. Amazon

35. When the Words “Tyrant” and “Dictator” Did Not Carry a Bad Odor

Merriam-Webster’s Dictionary defines a tyrant as an absolute ruler unrestrained by law or constitution; a usurper of sovereignty; or a ruler who exercises absolute power oppressively or brutally. A dictator is defined as a person granted absolute power; one holding complete autocratic control; a person with unlimited governmental power; or one ruling in an absolute or oppressive way.

Relatively few in modern society would welcome being ruled by a tyrant or dictator. However, the terms dictator and tyrant have a complicated history. For centuries in the days of the ancient Greeks and Romans, more people loved tyrants than feared them, and many accepted dictators as necessary. Indeed, in the Roman Republic, a dictator was not a usurper of power, but the legal holder of an office, appointed to that position by constitutional means.

The Top Benevolent and Malevolent Dictators From History
‘The Rape of Lucretia’, by Boticelli, depicting the assault and the popular uprising that it triggered. Wikimedia

34. Ancient Romans Detested the Absolute Power of Kings – But Had no Problem With Dictators

In 509 BC, a popular revolt overthrew Rome’s monarchy, and replaced the rule of kings with the Roman Republic. While Rome’s earlier kings had been revered, the last one, Tarquinus Superbus, or Tarquin the Proud, was overbearing. His family was worse: the uprising was triggered by one of Tarquin’s sons raping a Roman woman named Lucretia. Between such abuses and frequent fighting against Tarquins trying to regain power, the Romans developed a long-lasting loathing of kings and would-be kings.

The newly-established republic divided the government’s executive power between two annually elected officials known as praetors, later as consuls. Checks and balances were put in place to guard against the gathering of too much power in the hands in any one man – lest that tempt him to try and become king. Unfortunately, emergencies cropped up at times – primarily foreign wars, but sometimes internal crises – that required the concentration of the state’s powers in the hands of a single individual. That was pretty much the definition of a monarch, but the Romans detested monarchy and wanted nothing to do with it. So they created a constitutional office for such emergencies: the dictator.

The Top Benevolent and Malevolent Dictators From History
Roman Republic legion, from the era when dictators were common. Pintrest

33. The Roman Dictator Was a Temporary King

The Roman Republic’s system of checks and balances sometimes checked the exercise of governmental power too much at moments when the exercise of that power was urgently needed. The annually elected consuls were equal in power, and little could be done if they disagreed about something. In the republic’s early days, fears grew of an impending war against a coalition of powerful neighbors. Simultaneously, there were widespread suspicions that one or both consuls wanted to restore the monarchy.

The Top Benevolent and Malevolent Dictators From History
Rome’s steady expansion was the results of a series of successful wars against her neighbors. Wikimedia

So the Romans got together and decided to deal with the emergency by appointing an official whose powers were superior to those of the consuls. Designated a dictator – a term meaning “one who gives orders” – the newly-created official wielded absolute authority, including the power of life and death over others. His decisions were final, with no appeal to a higher authority. However, that presented the Romans with the dilemma that such absolute power smacked too much of the absolutism of the recently overthrown and detested kings. So they imposed a significant check on the power of the dictator: term limits.

The Top Benevolent and Malevolent Dictators From History
The Roman Republic’s Curiate Assembly. Alamy

32. To Avoid the Risks of Permanent Tyranny, the Romans Imposed Time Limits on the Office of Dictator

The Romans established a process for appointing a dictator. It began with the Senate authorizing one of the consuls to nominate a dictator. Either of Rome’s two consuls could make the nomination, but if they disagreed, they drew lots to decide which of them would choose the nominee. Next, the nomination was sent to Rome’s Curiate Assembly – later the Centuriate Assembly – for approval.

If the Assembly approved the nomination, it would then enact a special law to grant the nominee the extraordinary powers of a dictator. To guard against the possibility of the dictator turning into a permanent tyrant, the law granting him power limited his term to the longer of six months, or until the emergency that required appointing a dictator was over.

The Top Benevolent and Malevolent Dictators From History
Roman legion from the era of the Punic Wars. Pintrest

31. Rome Used Dictators During Emergencies for Centuries, Before Serious Abuses Brought the Office of Dictator Into Disrepute

The Roman Republic’s existence spanned five centuries, from 509 BC to 27 BC. During that time, dozens of dictators were appointed to deal with extraordinary emergencies. The appointments were most frequent during the 5th and 4th centuries BC, then began tapering off in the 3rd century BC.

Abuses of the office were few and far in between, and many dictators behaved in an exemplary manner that transformed them into Roman icons and national heroes. After 202 BC, no dictators were appointed for 120 years, until 82 BC, when a Roman general, Sulla, got himself appointed dictator. As will be seen, he was no benign dictator, and his abuse of the office caused many Romans to consider abolishing the position of dictator for good.

The Top Benevolent and Malevolent Dictators From History
Cincinnatus returning his fasces with ax head, the symbol of his power and authority as dictator. Wikimedia

30. Ancient Rome’s Most Beloved Dictator

Lucius Quintius Cincinnatus (519 – 430 BC) was one of the Roman Republic’s most admired figures. He was elected Rome’s consul in 460 BC, and was twice appointed dictator, in 458 BC and 439 BC. Cincinnatus became legendary for his selfless devotion to the republic during crises. He assumed extraordinary power when it was thrust upon him to deal with grave problems, then surrendered it when the crises were over.

Cincinnatus was a conservative patrician and a capable general who had opposed the plebeians’ – Rome’s commoners – demands for a greater share of power. He ended up on the losing side of that fight. When his son killed a plebeian and fled Rome, Cincinnatus’ opponents held him accountable and impoverished him with a huge fine. His possessions were reduced to a small farm, and he was reduced to manual labor at an advanced age, forced to toil in his fields with his own hands. That changed in 458 BC, when a military emergency cropped up that required the appointment of a dictator, and the Romans realized that the man whom they had recently reviled and ruined was the best man for the job.

The Top Benevolent and Malevolent Dictators From History
Cincinnatus at his farm when Rome’s emissaries arrived to inform him that he had been appointed dictator. Encyclopedia Britannica

29. Cincinnatus Became Antiquity’s Iconic Good Dictator

When a delegation arrived to inform Cincinnatus that he had been appointed dictator, they found him toiling in his farm. Whatever hard feelings he might have harbored towards his countrymen over the vitriol directed his way, and the fine that had ruined him financially, Cincinnatus put those sentiments aside in his country’s hour of need.

He put aside the plow and took up the sword, and led the Romans to a swift victory. He then promptly resigned the dictatorship and went back to laboring on his small farm. Cincinnatus was appointed dictator again in 439 BC, when Rome was threatened with an internal conspiracy. He put it down, then once more laid down his power as soon as the crisis was over, and returned to his farm.

The Top Benevolent and Malevolent Dictators From History
‘Cincinnatus Leaves the Plough to Dictate the Laws of Rome’, by Juan Antonio Ribeira. Wikimedia

28. Admiration for This Dictator Endured for Thousands of Years

Cincinnatus went down as one of the most revered figures of the Roman Republic, and as an exemplar of civic virtue, modesty, and outstanding leadership. His reputation endured long after his death, and long after the demise of the Roman Republic. Over two thousand years later, George Washington consciously sought to model his career after that of Cincinnatus.

The Top Benevolent and Malevolent Dictators From History
Statue of George Washington as Cincinnatus, resigning his command. Roman Roads Media

That comparison resonated with contemporaries during the Age of the Enlightenment, who knew their Roman history well. Thus, when America’s first president and first great general voluntarily laid down his power at the end of his second term and went into retirement, he was lauded as a modern Cincinnatus.

The Top Benevolent and Malevolent Dictators From History
Peisistratos. Alchetron

27. In Ancient Greece, Being a Tyrant Was Not Always a Bad Thing

The words dictator and tyrant are often used interchangeably. However, in ancient Greece, while a tyrant was like a Roman dictator in that he exercised one man rule with few checks on his power, the tyrant’s term was open ended, and lasted for as long as he could hold on to power. Also, to contemporary Greeks – at least initially – the word “tyrant” did not carry the modern connotations of brutal oppression. It had instead a narrower meaning of a populist strongman who, with a support base of commoners excluded from power by an aristocracy, overthrew an oligarchy and replaced it with his own one-man rule.

Many ancient Greek tyrants were wildly popular – except with the aristocracy. Commoners had little power in the aristocratic system, so they were no worse off if ruled by one tyrant than when they had been ruled by a small clique of nobles. Also, with the power of an overbearing aristocracy reduced, government under tyrants tended to be more fair, rather than wildly favoring the nobles.

The Top Benevolent and Malevolent Dictators From History
Ancient Athens’ agora, or marketplace and town square. Pintrest

26. Ancient Greek Commoners Fared Better When Ruled by a Tyrant Than When Ruled by Aristocrats

Ancient Greek commoners tended to be better off economically under tyrants. A tyrant, usually encouraged activities such as commerce and crafts and manufactures, that benefited commoners. Those types of pursuits were viewed by the aristocracy as socially gauche, and even threatening insofar as they destabilized the social order by making jumped up commoners as rich as or richer than their social betters.

By breaking the power of the aristocracy, an ancient Greek tyranny was often necessary first step on the road to democracy. It removed from democracy’s path the barrier of strongly entrenched nobles who had previously held power in a death grip, refusing to share it with commoners. Tyrants had an interest in weakening the aristocrats who had monopolized power for centuries. So they adopted populist policies that appealed to commoners, whose support was necessary for the tyrant’s continued hold on power. Only after the aristocracy had been weakened, and its stranglehold on power broken, was there an opening for democracy to emerge.

The Top Benevolent and Malevolent Dictators From History
Peisistratos entering Athens with his fake goddess. Ancient World History

25. Ancient Athens’ Poor Invited a Tyrant to Govern Them

The process of one-man-rule by a dictator, or tyrant, paving the way for democracy played out in Ancient Athens with Peisistratos (died circa 527 BC). Athens’ hill district was its most populous – and also most impoverished – region. Earlier, a reformer named Solon (630 – 560 BC) had enacted reforms that ended the aristocracy’s monopoly on power. He gave the people of the hill district, known as The Men of the Hill, the right to vote for the first time.

However, a vote was all that the hill district people got, and it was a meaningless vote at that: the system still left the aristocrats with a lock on actual power. So The Men of the Hill invited Peisistratos, a popular general and distant relative of Solon, to make himself tyrant. With their support, Peisistratos marched on the city in a procession headed by a tall girl dressed up as the goddess Athena. The “goddess” blessed Peisistratos and declared that it was her divine will that he be made tyrant. However, the other Athenians saw through the mummery, and chased Peisistratos and his followers out of town.

The Top Benevolent and Malevolent Dictators From History
Greek mountains and hills filled with silver mines. Wikimedia

24. Ancient Athens’ Wildly Popular Tyrant

After fleeing Athens, Peisistratos bought silver and gold mines in northern Greece and got rich off their proceeds. Then, investing his wealth in mercenaries, he returned to Athens and tried again, this time with a well-equipped private army instead of a girl dressed up as a goddess. It worked, and in 546 BC, Athens’ overthrew the government and had himself proclaimed tyrant. Peisistratos championed the lower classes, and his tyranny became a wild success.

He suppressed the feuding factions, exiled his aristocratic enemies and confiscated their land holdings. He broke the confiscated land into small farms, and redistributed them to his followers, thus cementing their support. He also loaned small farmers money for tools, lowered taxes, standardized currency, and enforced the laws even-handedly. Peisistratos also promoted the growing of olives and grapes, encouraged commerce and craftsmen, and funded popular religious rites such as the Dionysia. He promoted theater, culture, and the arts, built an aqueduct, implemented a public buildings program, and beautified the city. By the time Peisistratos died, circa 527 BC, Athens was peaceful and more prosperous than it had ever been, with a growing and increasingly affluent middle class.

The Top Benevolent and Malevolent Dictators From History
Ancient Greek vase depicting the assassination of Peisistratos son, and Hippias’ brother, Hipparchus. Martin von Wagner Museum, Wurzburg, Germany

23. Peisistratos Demonstrated the Upside of a Good Tyrant, but His Successors Demonstrated Tyranny’s Downside

A key problem with a dictator or tyrant that capable and benevolent dictators and tyrants are hard to find. For every capable and benevolent dictator or tyrant who advances the public good, there are many more incompetent ones who leave nothing but misery in their wake. Ancient Athens discovered that the hard way, when its wildly popular tyrant Peisistratos was succeeded by his sons.

After Peisistratos died in 527 BC, his sons Hippias and Hipparchus succeeded him as co-tyrants. At first, the siblings governed Athens competently and with a light hand. Then Hipparchus was assassinated in 514 BC in a private feud stemming from a romance that went bad. After his brother’s assassination, Hippias grew paranoid, and his rule became oppressive as he lashed out indiscriminately at enemies real and imagined. As Hippias grew ever more violent, and the number of victims and exiles forced to flee Athens grew, the popularity that tyranny had enjoyed since the days of Peisistratos faded.

The Top Benevolent and Malevolent Dictators From History
Cleisthenes. Short History

22. A Good Tyrant Removed the Obstacle of Aristocratic Power From the Path of Democracy, and a Bad Tyrant Triggered a Democratic Revolution

One of the exiles chased out of Athens by Hippias was Cleisthenes (flourished late 6th Century, BC). He began plotting with other exiles to overthrow the city’s tyrant. Invasion was considered, but Hippias had a well-equipped army, while the exiles did not, and lacked the funds for an army of their own. So they sought to enlist the help of Sparta, which had the Greek world’s best army, to liberate Athens.

To get help from the Spartans, who were known for their piety, the exiles bribed the priests of Delphi, the Greek world’s most important religious site and home of the Oracle of Delphi. For centuries, the Oracle had given petitioners cryptic answers that could be interpreted in a variety of ways. Soon as Cleisthenes bribed the priests, the Oracle suddenly began giving every Spartan petitioner who showed up the same straightforward and decidedly not cryptic answer: “Liberate Athens!“. So the Spartans marched into Attica in 508 BC, chased out Hippias and liberated Athens, then marched back home. The victors then began the messy process of creating democracy.

The Top Benevolent and Malevolent Dictators From History
Athenian coins from the days of Cleisthenes. CNG Coins

21. The Struggle to Replace the Rule of a Tyrant With the Rule of the People

After liberating Athens, the Spartans left the Athenians to govern themselves. They immediately split into rival camps: oligarchs and populists. The oligarchs, led by Isagoras, wanted government returned to the hands of the wealthy. The populists, led by Cleisthenes and comprising a majority of Athenians, declared Athens a democracy ruled by a popular Assembly. Cleisthenes’ camp prevailed, but the oligarchic faction solicited Spartan aid to forcibly overthrow the democracy. The Spartans, no fans of democracy, sent another army to Attica, overthrew the democracy, and replaced it with an oligarchy. Cleisthenes and 700 democracy-supporting Athenian families were exiled.

However, Cleisthenes and the exiles returned soon thereafter. The population rose up in revolt, and the aristocratic faction and the Spartans were besieged in the Acropolis, Athens’ fortified hilltop. The rebels allowed the Spartans to leave, but the Athenian anti-democrats were slaughtered to a man. Having decisively dealt with the oligarchic threat, Cleisthenes set about laying the groundwork for what would eventually emerge as the flourishing democracy of Classical Athens.

The Top Benevolent and Malevolent Dictators From History
Quintus Fabius Maximus Verrucosus. All Free Photos

20. The Underappreciated Dictator Who Rescued Rome

Roman dictator Quintus Fabius Maximus Verrucosus (circa 280 – 203 BC) was underappreciated by his contemporaries. That, despite the fact that he saved them from ruin, and saved Rome from extinction. Fabius was a statesman and general whose cautious delaying tactics and strategies early in the Second Punic War (218 – 201 BC) against the Carthaginian general Hannibal earned him the nickname Cunctator, or “the Delayer”. Fabius’ delaying tactics saved a Rome reeling from a string of humiliating defeats, and gave it time to recover its equilibrium and gird itself for a difficult and long war.

However, Fabius delaying methods were derided by more hot-headed Romans, who wanted to come to grips with Hannibal and destroy him in battle as soon as possible. The problem was that Hannibal was one of history’s greatest generals, and Rome at the time had none who were his equals. Each time they came to grips with the Carthaginian general and offered him battle, it was the Roman army, and not Hannibal’s, that was destroyed.

The Top Benevolent and Malevolent Dictators From History
Hannibal crossing the Alps into Italy. Medium

19. Fabius Was Appointed Dictator to Save Rome From Hannibal

At the start of the Second Punic War, Hannibal led an army into Italy, and won a series of crushing victories. That threatened Rome’s hold on Italy, as its allies joined Hannibal or declared neutrality. At the time, Fabius was a respected senior statesman. He had been elected Consul in 233 BC and 228 BC, as well as Censor – a highly prestigious position – in 230 BC.

Faced with the dire emergency posed by Hannibal, the Romans appointed Fabius dictator for six months. As seen below, he ended up saving his countrymen from disaster. Little thanks did he get, however: the Romans reviled and abused Fabius while he was saving them, because he did so in a manner that they considered timid and cowardly.

The Top Benevolent and Malevolent Dictators From History
Hannibal. Wikimedia

18. The Dictator Who Perfected Delay Tactics and Gave Them His Name

Fabius realized that Rome had no general at the time, including himself, who was Hannibal’s equal as a battlefield commander. So instead of marching out to meet Hannibal and offer him battle, he adopted delaying tactics and an attrition strategy that came to be known as “Fabian”.

Fabius shadowed the Carthaginian army, refusing to offer pitched battle. He gradually whittled his enemy’s strength with scorched earth tactics, coupled with attacks against his supplies and isolated detachments. That stabilized the situation, but it was resented by other Romans who took to calling Fabius Cunctator, or “Delayer”. It was meant as an insult, but it eventually became a badge of honor.

The Top Benevolent and Malevolent Dictators From History
Hannibal and his army celebrating their victory at the Battle of Cannae. World History Gallery

17. It Took a Catastrophic Defeat for the Romans to Realize that This Dictator Had Been Right All Along

Fabius’ delaying tactics gave a reeling Rome an opportunity to catch its breath and recover from the defeats dealt it by Hannibal. However, as soon as his six-month-term as dictator expired, Fabius’ overconfident countrymen amassed 87,000 men, the biggest Roman army to date, and marched off to crush Hannibal. The Carthaginian general was eager to let them try. At the Battle of Cannae in 216 BC, Hannibal adopted a brilliant tactical plan that was executed to perfection. He lured the overeager Romans into a double envelopment, and destroyed them. Of 87,000 Romans, only 10,000 escaped. The rest were slaughtered or captured.

There were no more snide comments and sneers directed at Fabius, and Cunctator became an honorific instead of an insult. Fabius was elected consul three more times before his death in 203 BC. His Fabian strategy became the official one followed by Rome for the remainder of the war, which was finally won in 201 BC. Fabius did not live to see the victory, but the erstwhile dictator laid the groundwork leading up to it.

The Top Benevolent and Malevolent Dictators From History
Sulla. The Romans

16. This Roman Dictator Was Definitely Not Benevolent

During its first few centuries, the Roman Republic was fortunate that no dictator went rogue and seriously abused the extraordinary powers handed to him. That good fortune ran out with the dictator Lucius Cornelius Sulla (138 – 79 BC), a general who led the Optimates – Rome’s conservative and aristocratic-leaning political faction.

Sulla did something that no Roman dictator or general before him had done: he led his legions in a march on Rome. Sulla seized power by force, and fought and won a civil war against the Populares – Rome’s progressive-leaning political faction. He then had himself appointed dictator, and massacred his political opponents by the thousands. Sulla also enacted constitutional reforms that were intended – but ultimately failed – to strengthen the Roman Republic in its final decades.

The Top Benevolent and Malevolent Dictators From History
Gaius Marius. Quora

15. This Dictator Started Off as a Seducer – and Murderer – of Wealthy Older Women

Sulla belonged to an old patrician family, but it was centuries removed from its heyday by the time he was born. He grew up dissolute and debauched, consorting with actors – a despised profession in those days. However, Sulla was strikingly handsome, so as a young man, he earned his keep by seducing and preying upon wealthy older women. At least two of them died in suspicious circumstances after naming Sulla as sole heir in their wills.

He began his political career in during the Numidian War (112 – 106 BC) as quaestor, or financial magistrate, for Rome’s then-greatest general, Gaius Marius. However, when Sulla captured the Numidian king by treachery and claimed credit for ending the war, he aroused Marius’ resentment. That was the start of bad blood between the two men. The consequences were dire: the shedding of rivers of actual blood, and kicking off a chain of events that eventually culminated in the collapse of the Roman Republic.

The Top Benevolent and Malevolent Dictators From History
Sulla attacking Rome. Imgur

14. Petty Jealousy Ends With a Roman General Leading His Legions on a March Against Rome

In 91 BC, the Social War broke out between Rome and her Italian allies and subjects, who demanded Roman citizenship and rights. Sulla performed brilliantly in that conflict, which ended in 88 BC. His erstwhile commander, Gaius Marius, who was aged and ailing by then, did not. In 88 BC, Sulla was elected consul, he was given command of a war against Pontus, in today’s Turkey. However, Marius engineered the enactment of a law that stripped the command from Sulla, and gave it to Marius instead.

Sulla responded by informing his legions that if Marius was appointed to command the war, he would use his own legions and not Sulla’s men. That would deprive Sulla’s men of the rich rewards they had expected in the form of booty from a successful war against Pontus. With their financial interests threatened, the legions supported Sulla in marching on Rome.

The Top Benevolent and Malevolent Dictators From History
An exiled Gaius Marius in Carthage, after he was chased out of Rome and Italy by Sulla. Wikimedia

13. Unlike Prior Roman Dictators, This Dictator Abused His Power in a Serious Way

When Sulla marched on Rome, Gaius Marius and his supporters were forced to flee. When Sulla eventually left to fight the war against Pontus, Marius returned to Rome with his own army in 87 BC. He had Sulla’s enactments reversed, executed about a dozen leading Sulla supporters, and in 86 BC, he was elected consul for an unprecedented seventh time. Marius’ seventh consulship did not last long: he died only 17 days into his term in office.

The Top Benevolent and Malevolent Dictators From History
Sulla posted public lists of those proscribed, marked for death and the confiscation of their property. Wikimedia

After winning the war against Pontus, Sulla returned to Rome with his army, defeated the Marians, and entered the city in 82 BC. He undid all the Marian legislations, introduced reactionary conservative constitutional reforms that solidified the power of the aristocracy and weakened that of the middle classes, and got himself appointed dictator. He then massacred the Marians and Populares by the thousands. Sulla posted proscriptions, or lists naming enemies of the state who could be legally killed by anybody in exchange for a reward and a share of the victim’s property upon presentation of his head to Sulla’s agents. He resigned in 79 BC, retreated into private life, and died the following year.

The Top Benevolent and Malevolent Dictators From History
Augustus. Encyclopedia Britannica

12. History’s Best Benevolent Dictator?

History’s best dictator was probably Gaius Octavius, better known as Augustus (63 BC – 14 AD), Rome’s first emperor. Octavius was born to an affluent plebian family on his father’s side, while his mother was of the patrician Julii lineage, and a niece of Julius Caesar. Octavius’ famous grand-uncle launched his grand-nephew into public life, and groomed him to be his heir. Octavius was in Albania, completing his military and academic studies, when Julius Caesar was assassinated in 44 BC.

The Top Benevolent and Malevolent Dictators From History
The assassination of Julius Caesar. Smithsonian Magazine

When he got back to Rome, Octavius learned that Caesar had adopted him as his son in his will, and made him his chief heir. He was advised to decline the dangerous inheritance, but he ignored the advice and went to Rome. There, Caesar’s lieutenant, Mark Antony, refused to honor the will. Caesar’s assassins, from the conservative faction known as the Optimates, ignored the teenaged Octavius. Cicero, one of Rome’s prominent elder statesmen and a leading figure of a politically powerful but militarily weak faction, sought to manipulate him, quipping that he would: “raise, praise, then erase” the young man. He was mistaken.

The Top Benevolent and Malevolent Dictators From History
A younger Octavius. Wikimedia

11. History’s Greatest Dictator Was Underestimated by Everybody

Just about everybody underestimated Octavius. They took him for a lightweight teenager who had nothing going for him except the famous Caesar name. However, the unprepossessing young man – he was frail and prone to illness throughout his life – was a master politician. So he set out to play the long game. The future dictator paid for public games in honor of Julius Caesar, his adoptive father. He sought to gain recognition and popularity, and lead Rome’s populist faction, fittingly known as the Populares. Octavius also set out to woo Caesar’s veteran soldiers to his side.

He succeeded beyond anybody’s expectations. With a military force at Octavius’ command, Cicero’s faction sought his aid. They bent the rules to appoint him a senator despite his being legally below the minimum age, and sent him against Mark Antony, who was forced to retreat from Italy to Gaul. The consuls in official command of the forces arrayed against Mark Antony were killed, so Octavius got the Senate to appoint him to a vacant consulship, once again despite being legally too young for the position.

The Top Benevolent and Malevolent Dictators From History
Cicero denouncing a Populares rival, Catalina, in the Roman Senate. Encyclopedia Britannica

10. The Rise of This Dictator Was Bad News for Rome’s Patricians

Once he secured himself a consulship, Octavius promptly double-crossed the very Senate and senators who had bent the rules to get him the position. He reached an agreement with Mark Antony, and joined him in a power sharing dictatorship. A generation earlier, after his victory in Rome’s first civil war, the dictator Sulla, head of the conservative patrician Optimates faction, had gone after the Populares faction that had stood for the Roman commoners.

Sulla murdered the Populares by the thousands in terrifying proscriptions. The conservative victory was not permanent, however. As seen below, once Octavius secured power at the head of the Populares, he paid back the Optimates in full, and with interest to boot.

The Top Benevolent and Malevolent Dictators From History
Octavius and Mark Antony overseeing the proscription of the Optimates in 43 BC. Alamy

9. This Benevolence of this Dictator Did Not Extend to His Enemies

A generation after the dictator Sulla’s proscriptions at the head of the patrician Optimates devastated the Populares faction, the pendulum swung when Octavius and Mark Antony, now leading the Populares, went after the Optimates. In even bloodier and more thorough proscriptions than those of Sulla against the Populares, the duo launched a massive purge that executed thousands of Rome’s conservative Optimates. They also killed other suspected opponents, including Cicero, who had tried to follow a centrist path only to end up offending both sides.

The Top Benevolent and Malevolent Dictators From History
Roman gold aureus depicting Mark Antony, left, and Octavius, right, struck in 41 BC to celebrate their power-sharing agreement. Coin Talk

Having slaughtered the conservative faction and broken its back for good, Octavius and Mark Antony next went to war against Julius Caesar’s assassins. They defeated them, and exacted revenge for the death of Caesar. In subsequent generations, in the Roman Empire, what remained of the patrician class was gradually killed off, as they were caught up in or were falsely accused of conspiracies against various emperors, until they became virtually extinct.

The Top Benevolent and Malevolent Dictators From History
Antony and Cleopatra. Fine Art America

8. After Removing His Enemies, Octavius Went After His Former Partner

After defeating their enemies, Octavius and Mark Antony swore friendship, and sealed their agreement to share power with Antony wedding Octavius’ sister. They then divided the Roman world, with Antony ruling the east, while Octavius stayed in Rome and ruled the west. However, the duo fell out when Antony fell in love with Cleopatra in Egypt, and married her, abandoning Octavius’ sister.

The future emperor used that family insult as a pretext to attack Antony. He defeated his former partner decisively in 31 BC, and became Rome’s sole ruler and de facto dictator. He then seized Egypt and the eastern provinces, which finally brought the entire Roman world under his control.

The Top Benevolent and Malevolent Dictators From History
Bronze bust of Octavius. British Museum

7. From Overlooked Teenager to Dictator, Emperor, and Founder of the Roman Empire

After he defeated Mark Antony, Octavius set about reorganizing the state. He ended the Roman Republic, whose political structure, created for a city-state, had proved impractical for the governance of a vast empire. The Republic’s fraying institutions had led to a century of chaos and bloodshed, until the reins of power were taken in hand by Octavius.

In recognition of his ending the generations of chaos and restoring stability, the Roman Senate granted Octavius the honorific title “Augustus”, by which he is known to history. In the Republic’s place, Augustus established the Roman Empire, with himself as its de facto dictator.

The Top Benevolent and Malevolent Dictators From History
‘The Emperor Augustus Rebukes Cornelius Cinna for His Treachery’, by Etienne Jean Delecluze, 1814 – Augustus pardoned Cinna and gave him a government job. Van Go Yourself

6. Augustus Declined the Formal Office of Dictator, While Accepting All the Powers of a Dictator for Life

Rome’s elites had hated Julius Caesar because of the perception that he wanted to be king – a title and position that the Romans loathed. As seen previously, although a traditional Roman Republic dictator had nearly absolute and semi-monarchical powers, his term was limited to a maximum of six months. In 82 BC Sulla had himself appointed dictator with no time limit set on his office, but he resigned the following year. By contrast, Julius Caesar had first gotten himself appointed dictator for ten years, then extended it to dictator for life. That made him king in all but name, so Rome’s traditionalists did away with him.

The Top Benevolent and Malevolent Dictators From History
Augustus. History

After Caesar’s assassination, the office of dictator was formally abolished. In 23 BC, the Senate offered to revive the office and make Augustus dictator. Well aware of his uncle’s fate and wishing to avoid a similar plot that could do him in, he declined. However, he accepted the executive powers of a consul for life, as well as those of a tribune – whose person was theoretically inviolate. Thus, Augustus effectively assumed the powers of a dictator for life, without the title. That setup was passed on to his successors.

The Top Benevolent and Malevolent Dictators From History
Augustus. Wikimedia

5. The Dictatorship of Augustus Ushered in the Most Prosperous Stretch of Roman History

The Roman Empire ushered in by Augustus as dictator in fact but not in name, replaced the Roman Republic. It was a stable, autocratic, and centralized de-facto monarchy, whose founding kicked off a period known as the Pax Romana. It brought the Greco-Roman world two centuries of peace, stability, and prosperity.

Augustus held power in the Roman world from 43 BC, first in conjunction with Mark Antony until 31 BC, and thereafter alone, until his death in 14 AD. As he lay dying, Augustus compared the role he had played as emperor to that of an actor on a stage. His last words to those gathered around his deathbed were: “Have I played the part well? Then applaud as I exit“.

The Top Benevolent and Malevolent Dictators From History
Vespasian. Wikimedia

4. From Humble Origins to Emperor

The powers of a de facto dictator were passed on to Augustus’ successors. They included Titus Flavius Vespasianus, better known to history as Vespasian (9 AD – 79 AD), who was born in an unremarkable Italian village to an undistinguished family. His ancestors included a common legionary who went on to become a centurion, a debt collector, and a small scale money lender with a clientele of barbarians. Vespasian rose from those humble origins to become emperor and found the Flavian Dynasty.

A self-made man, Vespasian entered the cursus honorum (the career ladder of Roman officialdom) as a military tribune. He rose steadily through military and civilian positions of increasing responsibility. His first big break came during the invasion of Britain in 43 AD. He displayed exceptional brilliance in command of a Roman legion, and his military talent earned him the esteem of Emperor Claudius. Vespasian’s success in Britain led to a consulship, but then he displeased the emperor’s wife and was forced to retire soon thereafter.

The Top Benevolent and Malevolent Dictators From History
Battle of the Medway during the Roman invasion of Britain, in which Vespasian shone. British Battles

3. Vespasian Lived Through The Year of the Three Emperors, and Decided to Make it the Year of the Four Emperors

Vespasian reemerged from retirement after Emperor Claudius’ death, and won favor with his successor, Emperor Nero. However, his revived career was derailed when he gave offense by falling asleep while Nero was giving a lyre recital. Vespasian’s fortunes sank so low, that he was forced to become a muleteer in order to make ends meet. His fortunes revived once again in 67 AD, when he was appointed to suppress the Great Jewish Revolt.

Vespasian was busily engaged in doing that, when Nero was forced to flee Rome and driven to suicide in 68 AD. In the subsequent scramble for power, competing governors and generals mounted the throne in quick succession. By April, 69 AD, the year was already known as “The Year of the Three Emperors”. Vespasian reasoned why not four?

The Top Benevolent and Malevolent Dictators From History
Vespasian. Museum of Classical Archaeology

2. Rome’s First Emperor From a Non-Senatorial Background

In the chaos following the fall of Nero, Vespasian seized the moment. He secured support in the Roman east, where he had been sent down to put down the Jewish Revolt, and declared himself emperor. He sent his forces to Rome, and by the end of 69 AD, he had won. That victory made him Rome’s first emperor who hailed not from a senatorial family, but an equestrian one – a social rank below that of senators.

Vespasian’s rule was successful, as he restored stability and good governance, and launched a massive building and public works program. Construction of Rome’s Colosseum, known at the time as the Flavian Amphitheater, was begun in his reign. It was completed and inaugurated in the reign of his son and successor, Titus.

The Top Benevolent and Malevolent Dictators From History
Bust of Vespasian. Capitoline Museum

1. Despite Wielding the Powers of a Dictator, Vespasian Never Lost the Common Touch or Forgot His Humble Origins

Despite having all the powers of a dictator, Vespasian was never full of himself, and had a reputation for wit and amiability. As emperor, he seldom stood on ceremony, but cultivated a blunt and even coarse mannerism, and was given to forthright speech. Never forgetting his humble origins, he resisted the temptation to put on airs, to which most Roman emperors succumbed. One of his revenue-raising schemes involved a tax on public urinals, which was widely ridiculed. His son and designated heir took him to task for that, arguing that it was beneath imperial dignity to collect revenue from bodily excreta.

Vespasian responded by holding a coin beneath his son’s nose, and asking whether he could smell any urine. He concluded by saying: “money does not smell” – which became a Latin proverb. Starting with Julius Caesar, who was declared a god after his assassination, Roman emperors who died in good repute were deified after death. When he felt the end nearing in 79 AD, Vespasian, in a final illustration of his lifelong penchant for not taking himself too seriously, joked just before dying: “dear me, I think I am becoming a god“.

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Where Did We Find This Stuff? Some Sources and Further Reading

Baker, George Philip – Sulla the Fortunate: Roman General and Dictator

Cassius Dio – The Roman History: The Reign of Augustus

Ehrenberg, Victor – From Solon to Socrates: Greek History and Civilization During the 6th and 5th Centuries BC (2010)

Encyclopedia Britannica – Augustus

Encyclopedia Britannica – Fabius Maximus Cunctator

Encyclopedia Britannica – Peisistratos

Everdell, William – The End of Kings: A History of Republic and Republicans (2000)

Forsythe, Gary – The Beginnings of the Republic, From 509 to 390 BC (2015)

Goldsworthy, Adrian – Augustus: First Emperor of Rome

Gonick, Larry – The Cartoon History of the Universe (1990)

Keaveney, Arthur – Sulla: The Last Republican (1982)

Livy – History of Rome, Book III

Livy – The War With Hannibal

O’Neil, James L. – The Origins and Development of Ancient Greek Democracy (1995)

Morgan, Gwyn – 69 AD: The Year of the Four Emperors (1937)

Plutarch – Parallel Lives

Suetonius – The Lives of the Twelve Caesars

Tacitus – The Histories

Wikipedia – Lucius Quinctius Cincinnatus

Wikipedia – Vespasian

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