5. The Ottoman Turks
First they spent two centuries conquering the remains of the Byzantine Empire while painting Romans as heathens, infidels, and all-around dumbasses — which, truth be told, they kinda were at that point.
Pictured: The late Byzantine Empire.
However, after capturing of Constantinople in 1453, it’s hard to argue that capturing the city did not kinda go to Mehmed II’s head. He began paraded himself around town as “Kayser-i Rum,” which literally translates to “Caesar of the Romans.” Politically, it made about as much sense as Harry S. Truman declaring himself the new Emperor of Japan after winning WWII.
However, he did have the clothes.
Despite Mehmed’s impressive capture of the city, his fancy title died along with him because his heirs knew he was fooling no one.
4. The Holy Roman Empire
For nearly 750 years, the Holy Roman Empire enjoyed a formidable reputation perhaps best described as the McDonald’s of the European nobility. However, after some frequent disagreements with the papacy and one too many bouts of inbreeding, the philosopher Voltaire eloquently captured with his pen what a monumental poser the empire was: “This agglomeration which was called and which still calls itself the Holy Roman Empire was neither holy, nor Roman, nor an empire.”
The gigantic mess was finally euthanized in 1806 by Napoleon, of all people.
3. Andreas Palaiologos
The nephew of Constantine XI Palaiologos, the last Byzantine Emperor of Constantinople, Andreas fled to Italy after his empire was completely overrun by the Ottomans. Despite owning a potentially legitimate claim to a title he called “Emperor of Constantinople,” the man was so broke that he—no joke—sold the rights to his empire to Charles VIII of France as if the whole thing was a record label.
After agreeing to sell the rights to his throne a few more times, Andreas died a pauper in 1502.
2. Pope Boniface VIII
This one should not be too surprising. However, some popes were better than others at establishing themselves as the political heirs to the Roman Empire. Pope Boniface VIII was not one of these people.
Pope Boniface VIII, the gold standard of asshole popes.
After making life hell for famous figures such as Dante Alighieri, Pope Boniface VIII realized that the Papacy wasn’t as all-powerful as he wanted. His solution to this problem was the Papal bull Unam sanctam, which essentially declared him King of Kings of Christian Europe and, thus, ruler of everyone. A French minister subsequently excommunicated by Boniface responded to this by dispatching a posse to kick his 68-year-old ass, which we do not mean in a figurative sense. They physically beat him up.
Guess who won the fight?
Boniface died a little over a month later of kidney stones/an ass-kicking.
1. Benito Mussolini
This genius’s idea of rebuilding Rome consisted of joining forces with Adolf Hitler and doing as much as possible to work with him militarily. It would have been a great idea if his plan was to make Germany lose World War II as quickly as possible.
And if WWII was really a fashion contest.
Despite being credited as a key figure in the creation of fascism, Mussolini developed a military resume during WWII comparable to a Gen. George Costanza. His strategy in Africa consisted of marching 130,000 men into Egypt just so they could surrender and forcing Germany to deploy their single best general into the area to clean up his messes.
When he invaded Greece in 1940, his overwhelmingly larger army was kicked out of the country and eventually forced to surrender Albania.
This particular blow hit the Axis hard since it forced Germany to sweep into the region and spend time and soldiers that otherwise would have been useful in Russia. By the end of his tenure, the war seemed so hopeless that his speeches actually demoralized the Italian people because even they could tell how full of shit their leader was.
Sure enough, Mussolini eventually found this out the hard way as well when he was captured and subjected to a death that made the ending of Inglourious Basterds seem tame.
Jacopo della Quercia is now on Twitter. Follow him!