Top 10 Historical Downgrades: Going from Good Leaders to Terrible, Awful Ones

We go from Akbar to Washington to Edward I, and their ignoble successors.  

Transcript

Top 10 Historical Downgrades: Going from Good Leaders to Terrible, Awful Ones 

July 2025

True leaders don’t invest in buildings. Jesus never built a building. They invest in people. Why? Because success without a successor is failure. So your legacy should not be in buildings, programs, or projects; your legacy must be in people. 

Myles Munroe

Civilizations are built by the ceaseless toil of a succession of generations. With softness and sloth, civilizations succumb. Let us beware of decadence. 

Rajiv Gandhi

The criteria for this list are pretty straightforward.  A leader, whether a ruler, president, or prime minister, must have demonstrated an outstanding ability to govern their nation.  Whether it be the ability to unite a country, fight off an invasion, or create a sense of prosperity, those are the criteria for the first name.  The 2nd name needs to represent a figure of such utter incompetence that, during their lifetime, they either undo the good of their predecessors or sow the seeds for the eventual chaos of bad governance to which their nations descended.  In this list, I left off the likes of Augustus, whom I feel was one of the greatest monarchs in history.  Tiberius was not as great as his predecessor, nor was he as notable as Vespasian or Diocletian.  But he was not terrible.  Now, his successor, Caligula, could have earned this crown, but he did not directly follow Augustus.  After all, Tiberius’Tiberius’ reign was 22 years.  

I also considered several figures, such as Kublai Khan and his successor, his grandson Temür Khan.  After all, it was after Kublai’s death that the preeminence of the Yuan Dynasty began to fade.  However, I would argue that the splintering of the Mongol world began under Kublai, and that Temür was not a terrible ruler.   

10. Akbar the Great to Jahāngīr

Akbar is considered, without doubt, to be the greatest Mogul Emperor.  At its height under Akbar, from 1556 to 1605, the Mughal Empire was the wealthiest and most powerful state in the world, with the possible exception of Ming China.  To preserve the unity of his empire, Akbar implemented programs that won the loyalty of the non-Muslim populations within his realm. He reformed and strengthened his central administration, centralized his financial system, and reorganized tax-collection processes. Although he never renounced Islam, he took an active interest in other religions, persuading Hindus, Parsis, and Christians, as well as Muslims, to engage in religious discussion before him. Illiterate himself, he encouraged scholars, poets, painters, and musicians, making his court a center of culture.  Akbar expanded the empire southward into the Deccan plateau and eastward towards Bengal, adding whole provinces. He also extended northwards into Kashmir and Afghanistan, the original home of the 

Moguls.   Akbar also reformed the army, the financial system, and the civil administration.  

Yet the later years of Akbar’sAkbar’s reign were marred by the revolt of his Jahāngīr.  Though not completely talentless, at different times he succumbed to addictions to food, opium, and drink.  

One Mogul noble, Prince Khurram, openly led a rebellion between 1622 and 1625. In 1626, Jahāngīr was temporarily placed under duress by Mahābat Khan, another rival for power.  Jahāngīr, a heavy drinker and opium eater—until excess taught him comparative moderation.  He also, copying his actions, witnessed a revolt from his own son Shah Jahan.  Though victorious, upon Jahāngīr’sJahāngīr’s death, Shah Jahan murdered his brother Shahryar, and other male Mogul heirs.  Typically, Jahāngīr might not have made this list, as we are not nearly as terrible a ruler as others on this list.  It was his fate to have succeeded someone like Akbar the Great.

9. Edward I to Edward II

In a few weeks, I will be creating the corollary to this list, which includes upgrades. Edward might be the only historical figure to make both lists.  His father, Henry III, though pious, was an ineffectual and spendthrift ruler.  Henry himself would have lost his throne were it not for the intervention of his son, Edward.  When Simon de Montfort, Earl of Leicester, rose against Henry, he was initially successful.  But due to Edward, almost despite his father, Simon was defeated.  

Edward later went on to crusade in the Holy Land, where he learned of Henry’s death upon his return.  He formerly conquered Wales and transformed the region from a collection of nobles who swore allegiance to the English crown to one where the King himself managed affairs. 

Edward also temporarily conquered Scotland, though, as we shall see, this was not a permanent acquisition.  Nevertheless, Edward I earned the nickname Hammer of the Scots along with that of Longshanks, due to his height and the length of his legs.  Simply put, he was an imposing and majestic presence.  

Edward I, who reigned from 1272 to 1307, is often referred to as the “English Justinian” due to his significant legal reforms. Edward also strengthened the role of royal courts, making them more central to the administration of justice. 

And as with all great historical figures, there are flaws.  It was not just that Edward was an antisemite. We will not impose our moirés upon the past, a term called presentism, because most Christians of Edward’sEdward’s day had the same views.  Instead, his expulsion of the Jews from England set up serious financial issues for his successors as they lacked this banking outlet for their costly reigns, thanks to Edward.  

Yet Edward I is considered, rightly, the greatest medieval English king.  His son was one of the worst. Edward II was a man of limited capability who waged a long, hopeless campaign to assert his authority over powerful barons.  He earned the hatred of the barons by granting the earldom of Cornwall to his frivolous favorite (and possible lover), Piers Gaveston. In 1311, a 21-member baronial committee drafted a document—known as the Ordinances—demanding the banishment of Gaveston and the restriction of the King’s powers over finances and appointments.

In 1314, Edward led an army into Scotland but was crushed by Robert the Bruce at Bannockburn on June 24. With one stroke, Scotland’s independence was virtually secured, and Edward was put at the mercy of a group of barons.  After many ups and downs throughout the reign which saw first the barons, then Edward on top, marked by his ability to choose the wrong people often, his own wife, Queen Isabella of France, and her lover, Roger Mortimer, invaded England, executed the Despensers, and deposed Edward in favor of his son, who was crowned (January 1327) King Edward III. Edward II was imprisoned and, according to the traditional account, died in September 1327, probably by violence though of being rammed with a poker up his backside (supposedly Queen Isabella’sIsabella’s revenge for his proclivities, is probably false.  

8. George Washington to John Adams

One of the most incredible aspects of Washington, the indispensable man of the Revolution, was not that every decision he made as president was the first for a continental-wide republic. Instead, it was that he got so many of the correct answers.

His successor, however, got it wrong too many wrong. One of Adams’sAdams’s first acts as president was an attempt to retain Washington’s cabinet secretaries. However, the secretaries took their orders from Alexander Hamilton and worked to undermine Adams’sAdams’s foreign policy agenda and reelection campaign in 1800.  Adams’sAdams’s presidency was also marred by the Alien and Sedition Acts, which targeted immigrants and political opponents of the Adams administration.  permitted the government to deport foreign-born residents and indict newspaper editors or writers who published “false, scandalous, and malicious writing or writings against the government of the United States.”  To my eyes, this is a blatant violation of the 1st amendment.  To Adams’ credit, he ended the “quasi-war” with France, but given that country’s continental problems, I would imagine they wanted Peace as much as Adams.  

7. James I to Charles I 

This one is tricky.  Was James a “great king?”  He carried the sobriquet “the British Solomon,” so he was certainly intelligent. I rank him high because he had the challenging task of merging, after 300 years of incessant war, the crowns of Scotland and England into a single kingdom, which required intelligence and finesse. The opening years of his reign as king of Great Britain were a time of material prosperity for both England and Scotland.

For one thing, he established peace by speedily ending England’s war with Spain in 1604. One of James’sJames’s faults was his inability to manage Parliament with the same finesse as his famous predecessor, Elizabeth I.  Besides the political problems that he bequeathed to his son Charles, James left a body of writings which, though of mediocre quality as literature, entitle him to a unique place among English kings since the time of Alfred.  And of course, there is the “King James” version of the bible.  

Charles had all of his father’s desire for greater crown control, with none of his wisdom or circumspection.  His demand for greater powers for the crown in the face of Parliament was not entirely new, but rather a continuation of a struggle dating back to 1215.  Charles has many attributes, including a strong work ethic and resolve that enabled him, for example, to overcome a stutter when speaking in public.  However, it was his self-righteousness, inflexibility, and sometimes pig-headedness that helped create a Civil War, which he lost, along with his life.  He tended to try to bludgeon his way through difficulties by invoking his authority, assuming that once his wishes were known, his subjects would stop squabbling and obey him. This ignored the expectation that there should be a good deal of give and take in the execution of royal policy and that where policies were unpopular, these should be blamed on royal counsellors. 

6. Winston Churchill to Clement Attlee

Winston Churchill was the man who kept Britain intact and played a crucial role in helping win the Second World War. If you have heard any bunk about his starting the war, look at my September 2024 podcast on the subject, and realize you are being fed snake oil.  Without Churchill, I believe Germany would have signed a dishonorable peace with Germany, enabling the latter to focus all of their efforts against the Soviet Union with disastrous results.  

But in one of those oddities that come with democratic government, just when Churchill had completed his work in 1945, the British public voted him out, and Labour Party leader Clement Attlee in as Prime Minister.  

He presided over the establishment of the welfare state in Great Britain and the granting of independence to India, the most crucial step in transforming the British Empire into the Commonwealth of Nations. He was perhaps the leading Labour politician of the 20th century. He transformed his party into the natural opponent of the Conservative Party, thereby polarizing British politics.

Atlee crafted a firm program of nationalization, including coal, railways, gas, and electricity. One of the highlights of his administration was its social reforms, including the creation of the National Health Service. Together, these programs shifted the British political agenda in a moderate-left direction for a generation.  Now, if you prefer your leaders to be leftist in makeup, there is much to love about Attlee. However, I believe it was Attlee who oversaw the nation’s permanent leftward tilt and subsequently contributed to the decline of what was once the world’s greatest power.  

5. Charlemagne to Louis the Pious

Between the fall of the Western Roman Empire in 476 and the reign of Charles V Habsburg, Charlemagne, King of the Franks and Lombards, and later the first Holy Roman Emperor, was the most powerful figure in Western Europe over the 1,100 years that followed.  Inheriting the Crown of the Franks from his father, Charlemagne would go on to conquer Italy, Saxony, a buffer state between Spain and the Rhine, and territories along the Upper Danube.  And in 800, he was crowned with the aforementioned title (well, a variation of it) that would last until 1806.  He was a towering figure.  However, in the Frankish tradition, he initially planned to divide his realm among all his living sons.  Fortunately for the youngest, Louis, his older brothers died, enabling him to receive the Kingdoms and the title of Emperor intact.  Unfortunately for the Carolingian dynasty, Louis was not that effective as a ruler.  

Louis I the Pious (814–840) was a man in every way different from his father. Whereas Charlemagne was decisive, Louis dithered.  Louis I’s proposals of succession aroused the conservative opposition of the Frankish nobility, and soon the Frankish lands were involved in civil war. Furthermore, internal dissension helped the papacy, which increased its influence by favoring one party or the other.  Louis experienced several revolts among his own children, and he was the last Carolingian to preside over a unified realm.  One of his legacies, however, was that his sons eventually created the modern states of France and Germany, with a slice of territory between them that became similar to a bone over which two dogs are constantly fighting.  

4. Ashoka to Dasharatha Maurya

Ashoka the Great (r. 268-232 BCE) was the third king of the Mauryan Empire (322-185 BCE), best known for his renunciation of war, development of the concept of dhamma (pious social conduct), and promotion of Buddhism as well as his effective reign of a nearly pan-Indian political entity.

At its height, under Ashoka, the Mauryan Empire stretched from modern-day Iran through almost the entirety of the Indian subcontinent. Ashoka was able to rule this vast empire initially through the precepts of the political treatise known as the Arthashastra. 

After the death of Ashoka and the succession of Dasharatha, the Mauryan Empire began to decline. Hence, he became the ruler of the declining imperial rule. The Mauryan Empire received a massive setback as several territories broke away from Mauryan rule during his reign. He continued the social and religious practices established by his grandfather, Ashoka. Also, he was the last ruler of the Mauryan dynasty to issue imperialistic inscriptions, as no detailed records have been found of other Mauryan rulers who succeeded him.

The political unity of the Mauryan Empire did not long survive Ashoka’sAshoka’s death. One of Dasharatha’s uncles, Jalauka, set up an independent kingdom in Kashmir. Another Mauryan prince, Virasena, declared himself king in Gandhara. Vidarbha also seceded. Evidence from Greek sources confirms the loss of the north-western provinces, which the Mauryan ruler then ruled. There is also much modern speculation about a possible east–west division of the empire involving Dasharatha and another Mauryan ruler. Epigraphic evidence indicates that Dasharatha retained imperial power in Magadha.  There were also defections in the south.  In other words, none of the kings, after Ashoka, were powerful enough to hold the territories under the central authority. Due to this, the Mauryan Empire started to decline and completely collapsed within 50 years of Ashoka’s death, not that of his grandson.  The fact that Dasharatha only ruled for 8 years after his grandfather’s 34-year reign tells volumes.  

3. William Taft to Woodrow Wilson 

Was Taft a great president in the lexicon of Washington, Lincoln, or Reagan? (You probably thought I was going to put FDR in there, but for reasons I will not elucidate here.) He was not great.  But Wilson was, in my opinion, the worst president in the history of the Republic.  Yup, even worse than Buchanan, who was preceded by two ineffectual presidents and also the inevitability of the Civil War.  

Taft was caught between the massive personality (and ego) of Teddy Roosevelt and the cunning progressive reign of Wilson.  Unlike Roosevelt, Taft did not believe in the stretching of presidential powers. He once commented that Roosevelt “ought more often to have admitted the legal way of reaching the same ends.” Which, for this constitutionalist, is all to the good.  Taft alienated many liberal Republicans, who later formed the Progressive Party, by defending the Payne-Aldrich Act, which unexpectedly continued high tariff rates. A trade agreement with Canada, which Taft pushed through Congress, would have pleased eastern advocates of a low tariff, but the Canadians rejected it. He further antagonized progressives by supporting his secretary of the interior, who was accused of failing to carry out Roosevelt’s conservation policies.  

And yet, despite a decision by the narcissistic Roosevelt, Taft would have won reelection against Wilson in 1912.  But TR could not stand to see his successor undo any of his policies, so believing himself to be invaluable, he ran as a third-party candidate in 1912.  This split the GOP vote, giving Wilson the White House.  Yet, unlike pretty much every other president, Taft came out OK, having been named Chief Justice of the Supreme Court in 1921 – the job he coveted more than the White House, and serving in that role for 9 years.  

There is so much to despise about Wilson.  As the champion of a living Constitution, no one has done more in this country to remove the concepts of separation of powers and checks and balances, and give more and more power to the executive than Wilson.  He once described the American people as “bees” all working toward a single end, as opposed to individuals.  And he was as much the egoist as Roosevelt, believing himself to be capable of making all the decisions.  He built the progressive model that has been the natural fit for FDR, LBJ, and Barack Obama.  And even the left has something to hate.  Wilson was a eugenicist who believed that African Americans were an inferior race.  

Taft may not have been among our greatest presidents (though he should be in the top 25), but his successor was the worst.  

2. Qin Shi Huang (Qin Dynasty) to Qin Er Shi

Born Zhao Zheng, Qin Shi Huang of the Qin dynasty (221–207 bc) and creator of the first unified Chinese empire (which collapsed, however, less than four years after his death).  By 221, with the help of espionage, extensive bribery, and the ruthlessly effective leadership of gifted generals, Zheng had eliminated one by one the remaining six rival states that constituted China at that time, and the annexation of the last enemy state, Qi, in 221 marked his final triumph: for the first time China was united, under the supreme rule of the Qin.

To herald his achievement, Zheng assumed the sacred titles of legendary rulers and proclaimed himself Qin Shi Huang (“First Sovereign Emperor”). With unbounded confidence, he claimed that his dynasty would last “10,000 generations.”

As emperor, he initiated a series of reforms aimed at establishing a fully centralized administration, thus avoiding the rise of independent satrapies. Following the example of Qin and at the suggestion of Li Si, he abolished territorial feudal power in the empire, forced wealthy aristocratic families to reside in the capital, Xianyang, and divided the country into 36 military districts, each with its military and civil administrators. He also issued orders for almost universal standardization—from weights, measures, and the axle lengths of carts to the written language and the laws. Construction of a network of roads and canals was begun, and fortresses erected for defense against barbarian invasions from the north were linked to form the Great Wall.  Though later dynasties would perpetuate the union of China begun by Qin Shi Huang, his dynasty would survive only two generations.  

His son Qin Er Shi proved to be incompetent and lived surrounded by sycophants, ultimately leading to the dynasty’s collapse.  He was put on the throne by politicians Li Si and Zhao Gao, circumventing his brother Fusu, who had been the designated heir. Upon Huhai’s ascension, both Fusu and the popular general Meng Tian were killed on the orders of Li and Zhao, with Qin Er Shi’sShi’s role in the assassinations remaining uncertain and controversial. A weak ruler, Qin Er Shi’sShi’s reign was completely dominated by Zhao Gao, who eventually forced him to commit suicide. By the time of his death, the Qin Empire’s power had lessened so much that his successor Ziying ruled as a king, not emperor. 

1. Marcus Aurelius to Commodus 

I also thought of Septimius Severus, Caracalla, and Geta about this survey.  After all, Severus unified the Empire.  Yet his reign was not the triumph of Marcus Aurelius in terms of his overall contributions to history.  Nor do I think that Caracalla was a worse Emperor than Commodus.  Additionally, Commodus inherited an Empire that had enjoyed a relatively successful period for 80 years.  Previous to his father, Caracalla’sCaracalla’s time was one of chaos and division.  

In some regards, it is challenging to separate Marcus Aurelius, a successful Roman Emperor, from Marcus Aurelius, a Stoic philosopher.  I can trace elements of all these men’s times to the present day, especially with that of Washington.  But Marcus stands alone in claiming our hearts and minds. 

Marcus’Marcus’ rule was one fraught with continuous wars on nearly all frontiers, the rise of Christianity as a threat to the state, the dilution of silver as a coin of the realm, rebellions, and worst of all, a plague that killed nearly 10% of the population.  And in many regards, Marcus’sMarcus’s approaches to all of these issues are subject to scrutiny, not all of it positive.  He was not as great or as successful an emperor as Augustus or Vespasian before him, or Diocletian and Constantine after him.  However, in terms of managing all these issues, he maintained a unified empire and the loyalty of his subjects.  

Much has been made of his departure from the successful tradition of his four immediate predecessors in naming his son as his successor—two points to consider regarding this choice.  At the time of his death, Commodus was not the monster portrayed in the movie, especially the one depicted in Gladiator.  Second, not naming him would have immediately set up a possible civil war, as Commodus would be instantly a source of a faction.  Before the so-called Five Good Emperors, the precedent of selecting by family members had been established by the Julio-Claudians, and in the case of the Flavians, the transfer of power from father to son was a common practice.  

It is through Stoic philosophy that most people are familiar with Marcus today, primarily through his work, Meditations, a copy of which sits in my library.  It is difficult to watch so many of our people today struggle through life, voice unending complaints, and seek pleasure in some screen, despite the greatest prosperity in the history of our planet, and when I contemplate this, it is hard to see the wisdom of Marcus Aurelius.

“You have power over your mind, not outside events. Realize this, and you will find strength.”

“The happiness of your life depends upon the quality of your thoughts.”

“When you arise in the morning, think of what a privilege it is to be alive, to think, to enjoy, to love ...”

“If someone can show me that what I think or do is not right, I will happily change, for I seek the truth, by which no one was ever truly harmed. It is the person who continues in his self-deception and ignorance who is harmed.”

The irony of Marcus’sMarcus’s actual life is how much of his great philosophy was lost on his son. Cassius Dio, for example, claims that he was not naturally evil, but instead surrounded himself with depraved individuals and lacked the guile and insight to resist their insidious influences.  It was also Cassius Dio who wrote of the death of Marcus (from natural causes, there is no evidence that Commodus murdered him – again, thanks a lot, Ridley Scott) and the accession of Commodus. This marked the moment when the empire descended from “a kingdom of gold, to one of rust.” Indeed, the accession of Commodus as sole ruler has forever marked a turning point in the decline of Roman history and culture, as intermittent civil war, strife, and instability primarily characterized the next few centuries of Roman rule.  

Initially, despite uprisings in Britain and North Africa, and furthering his father’s policy of debasing the gold, Commodus’sCommodus’s direct reign was mainly one of peace and relative prosperity across the empire.  That was to change as Commodus’sCommodus’s disinterest in governing led to increasing unrest.  

The senatorial class despised him for his lack of attention to his duties, his preference for lackies, and his favoritism towards the army. The general public and soldiers seemed to be quite fond of him. Indeed, for the former, he regularly put on lavish shows of chariot racing and gladiatorial combat, which he would on occasion take part in.  So plots arose, and the more attempts were made on his power and life, the more it fueled his sense of paranoia, thus creating more plots.  Whilst it is tough to ascertain whether any of these were genuine plots against him, it seems clear that Commodus quickly got carried away and began to undergo a campaign of executions, clearing out the aristocratic ranks of almost everyone who had become influential in the reign of his father. 

Eventually, Commodus descended into madness, and after a 12-year rule, a trio of conspirators had him strangled in his bath (again, he was not killed in the Coliseum in gladiator garb).  Rome had managed to quickly right itself after the deaths of mad Emperors Caligula, Nero, and Domitian.  Such restoration was not happening this time.  Following Commodus’sCommodus’s death, the Roman Empire descended into a violent and bloody civil war, in which five different figures competed for the title of emperor, a period that was accordingly known as the “Year of the Five Emperors.”  Although some emperors, such as Septimius Severus, enjoyed a unified reign, the time of Roman prosperity would not be revived until the late 200s, a century after Commodus’ death, by the Emperors Aurelian and Diocletian.  

Marcus Aurelius was a strong Emperor who wrote philosophical works that are read widely today. His son initiated 100 years of “rust.”  That is why Commodus is the biggest downgrade in history.