Top Tier Losing Generals/Leaders

Lets face it History has some great generals and some opponents who were nearly as great and others who are merely the opponent who faced the great guy.

To get at what I mean, nobody thinks Darius the 3rd was in the same league as Alexander. But Hannibal and Scipio Africanus are closer to equals. If anyone would have defeated Julius Caesar, it would have been Vercengetrix, not Pompey, even though Pompey had a better 'starting position' of being part of the Roman War machine vs the 'Gallic' one IMHO, though reasonable people might disagree.

Guthrum seems to have had some very bad 'dice rolls' vs Alfred though Alfred was great at making sure that the Norse would not have another shot at Wessex. But Guthrum the Conquerer could be a thing.

Lee was good. Grant was better.

So, who are your top tier losers?
 
Richard I vs. Saladin? Saladin gained the upper hand, but Richard I was still very skilled.
Post-1900 example: Erwin Rommel was legitimately dangerous and skilled. However, the Allies had better generals, logistics, and industry.
 
Eumenes of Cardia
Pyrrhus of Epirus
Quintus Sertorius
Vercingetorix
Cao Cao
Constantine XI
Caspar Röist
Albrecht von Wallenstein
Louis-Joseph de Montcalm

Charles Cornwallis
Charles O'Hara (twice)
Hyder Ali
Archduke Charles
Shaka Zulu
Manuel Fernández Castrillón
Joseph E. Johnston
William S. Rosecrans
Joseph Hooker
Jubal A. Early
George A. Custer
Crazy Horse
Alexander von Kluck
 
Lets face it History has some great generals and some opponents who were nearly as great and others who are merely the opponent who faced the great guy.

To get at what I mean, nobody thinks Darius the 3rd was in the same league as Alexander. But Hannibal and Scipio Africanus are closer to equals. If anyone would have defeated Julius Caesar, it would have been Vercengetrix, not Pompey, even though Pompey had a better 'starting position' of being part of the Roman War machine vs the 'Gallic' one IMHO, though reasonable people might disagree.

Guthrum seems to have had some very bad 'dice rolls' vs Alfred though Alfred was great at making sure that the Norse would not have another shot at Wessex. But Guthrum the Conquerer could be a thing.

Lee was good. Grant was better.

So, who are your top tier losers?
Actually, Lee was probably better at strategy, and army management. Grant was great in that he understood that he was actually able to take advantage of the weaknesses in the Army of Virginia.

Stonewall Jackson
Napoleon, I mean he was defeated in the end.
Von Hindenburg
Gustavus Adolphus
 
Sextus Pompey.

This makes me think of some interesting alternate match ups/meet ups.

Sextus Pompey, Consul of Rome, retrieving the Eagles lost by Julius Ceasar, either against or in collusion with Vercengetrix, King of the Gauls, in order to outmanuever his political rival Octavian.
 
So, who are your top tier losers?
There are a fair few examples where one side was simply outmatched, whether in terms of technology or overall resources. E.g., Manco Inca, the last emperor of the Incas, or Caractacus, the leader of the British resistance against the Romans.
 
what is the definition of a losing general?

I have a very hard time calling Napoleon a losing general. Or Robert E Lee. or Hannibal. Sure, there sides ultimately lost the wars, but with the significant number of battles in the win column vs the small number in the loss column???

Now an Arch Duke Charles who usually showed pretty well, but usually lost against Napoleon and the French; yeah, pretty sure he would fit in the top-tier losing general description however loosely or strictly its defined.

Or maybe not. If Napoleon is defined as a top-tier losing general, can ANY general who lost a battle to him then also be considered a top-tier losing general? I mean you lost to a loser, what does that make you?
 
what is the definition of a losing general?

I have a very hard time calling Napoleon a losing general. Or Robert E Lee. or Hannibal. Sure, there sides ultimately lost the wars, but with the significant number of battles in the win column vs the small number in the loss column???

Now an Arch Duke Charles who usually showed pretty well, but usually lost against Napoleon and the French; yeah, pretty sure he would fit in the top-tier losing general description however loosely or strictly its defined.

Or maybe not. If Napoleon is defined as a top-tier losing general, can ANY general who lost a battle to him then also be considered a top-tier losing general? I mean you lost to a loser, what does that make you?
In my mind, a losing general is someone whose career is made by losing battles while a top-tier losing general would be someone like Archduke Charles who is most remembered for his hard-fought defeats. So someone like Albrecht von Wallenstein or Louis-Joseph de Montcalm wouldn't seem like a top-tier losing general because both of them made their careers through their victories, even if toward the end they lost. Even someone like Cumberland would be hard to qualify as a losing general because technically his career was made through his bravery at Dettingen and his victory over the Jacobites at Culloden. However, I guess you could say that once he was put in command and faced standard European armies he only ever really saw defeat, but those defeats were probably too severe to designate Cumberland as top-tier. In my opinion, a really really good example of a losing general is Prince Charles Alexander of Lorraine because he basically spent his career getting beat by Frederick the Great. Maybe you could call Charles Alexander a top-tier general because of how close some of his defeats were and because of his successes against Bavaria, but that's up to someone else to decide. I just think that a career like Charles Alexander's is a great model of what a losing general should be. But that's just my opinion.
 
You know, playing a lot of wargames, you play them as a match, once as the defender, and once as the attacker. One way to frame this is:
How would General (fill in the blank) fare against General (fill in the blank) if their places were reversed?
 
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