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I agree that "greatest" is too wide of a window, if you are a person accustomed to measurable variables.

The entire premise of the question is likely flawed, in that the demands of time and place change what is "great".

I don't think winning every time is tied to "greatness", maybe because of my Celt blood?

Leonidas, King of the Spartans, and his 300 Spartans, and 1100 Thespians, against hundreds of thousands of Persians, at Thermopaleae, in 480 BC?

Vercingetorix, who at Alesia (52 BC), did everything wrong, while Caesar did everything right.

Boadicea (Boudicca) queen of the Iceni against the Romans (60-61 BC)

Or the last queen of Carthage, whose name is unknown to me, who threw her children back into her burning city, and then jumped into the same fire after them, rather than joint her husband in disgrace and dishonor, who had just surrendered Carthage to the Romans who were putting the entire city to the sword except him and his family?

I know we are talking military commanders but, you just cannot ignore the traditions of self aware sacrifice, examples of leaders, if not truly Commanders.

It seems to me, that batting a thousand, is not a reasonable requirement for greatest military commander. In fact, it is how great commanders deal with defeat, that shows the depth of their greatness.

Jes my .02

I think that how commanders deal with their defeats shows their wisdom and their humanity and other traits. But if the criteria is military greatness, I think that victory is the coin of the realm. Much like football or chess games: how a side deals with defeat shows their mettle, teaches things, etc. But the unbeaten team at the end of the season is still the best team.

The Celts military history shows their passion for war but also the flaw in the civilization. Hot blooded, they spoiled for a fight. But they could not long endure any sort of discipline and command over them in any sort of supra-clannish way. The result: wild warfare, but the more organized states steadily plowed them under. Celts would fight Celts in the face of a foreign threat. And in the end lost their land to the foreigner - the classic case of hanging separately because of the adamant, persistent, cultural refusal to hang together.