Who do you think are the greatest losers in history...and you favourite?
Who do you think deserves the "historical facepalm award" for his failures?
Perdiccas: one of Alexander's "tier one" generals,Perdicca decided to assert himself after the death of the King of Makedon, but failed to unite most of the Diadochi and was soon despised by his own officers, who decided to have him assassinated in 321.
Crassus(115-53 BCE): despite his enormous wealth, he is mostly remembered for being the least talented of the triumvirs and for his disastrous campaign against the Parthians that led to his violent death.
Sigismondo Pandolfo Malatesta(1517-69): one of the most sought-after condottieri of his time and lord of important cities like Rimini,Fano and Senigallia. Due to an "unfortunate" twist of events, he was left out of the Peace of Lodi and found himself against most of the Italian powers(the Pope, the King of Naples,Venice the Duke of Urbino).At the end he lost everything,save a small strip of land around Rimini(where the construction of the Malatesta Temple was stopped due to a lack of fundings). He died from malaric fever after a difficult campaign against the Ottoman Empire,started in order to "re-establish" his reputation.
He is considered the "best loser in history" by Ezra Pound.
Charles of Burgundy(1433-77)(my favourite


): the man who wanted to create an empire stretching from the Mediterranean to the North Sea and with the best army of his time simply ended up repeatedly beaten by the Swiss Confederation(nothin' more than a bunch of mountain men) until he was himself killed at Nancy
Imagawa Yoshimoto(1519-60: the daimyo who wanted to assert his authority over Kyoto an beyond, was caught with his fundoshi down by Oda Nobunaga, who destroyed his ambitions in just a moment, when he ambushed Yoshimoto's 30 thousand strong army with just 300 hundred warriors and gave a terrible headache to the Imagawa daimyo.
Takeda Katsuyori(1546-82): the heir of Takeda Shingen, one of the greatest daimyo of Japanese history, decided to honour the memory of his late father with an in style offensive against the province of Mikawa,the military operations obviously ended in a failure: Katsuyori lost most of his army and his veteran generals during the battle of Nagashino(1575) against Oda Nobunaga, who permanently cancelled him from the political map of Japan in 1582, after years of somewhat miserable resistance.
Moreover, Katsuyori never proved to be a good administrator of the lands inherited by Shingen.
One of my favourite "facepalm" events in history is undoubtedly the Imperial Election of 1519: the king of France Francis I decided to bribe the electors before the vote in order to get their support, while Charles said to them "i will simply pay you after my election"; so the electors doubled the profit, at the expenses of the "unwise" Francis

.